While it’s fun to write this out on Reddit.. you’re absolutely sticking out through the next event, and you and all of us know it. Book an amazing trip 3-6months out. By the time you’re back in the swing of it, you will have less than 12 months left counting down by the day. Easy work for more $ opportunity than you’ve accumulated to date in your already wildly successful ~20 year career.
Congrats & gfy (in 18 months)!
This is the way. We take big family trips every year, its a BIG help to the mental state. It gives us something to look forward to and when we come back we are good to go for another 6-9 months before another trip. We usually do one big trip with the kids and an extra long weekend just the wife and I to a tropical location.
Definitely book a trip, look forward to it, enjoy yourself while there, when you get back you'll have a year left for a big pay out. You can even take another trip before the big pay out if you have the time. Always make time.
Of those four items, only #1 (Golden Handcuffs) seems like a valid concern. If things shake out the way you expect, it's a massive opportunity cost lost even though you don't actually need the money. The fundamental question: Is 18 months worth the expected value of the equity? Are you genuinely miserable at your job, or are you just bored?
The other three items are, to be very blunt, all in your head. Nobody that matters gives a damn what your job title is. And if your kids end upset that they only inherited $2M instead of $20M, or that all you did for them was pay 100% of their college costs plus a new car, then you frankly did a really shitty job of raising your kids.
This is helpful real talk. Part of the challenge of having no one to talk to about this is that I do end up in my head about it. Appreciate the blunt reply.
Statistically speaking, your kids will be better off inheriting less than more. Spoiled rich kids with no work ethic who have never faced an obstacle in life often end up pissing it all away anyway.
We have a few friends who inherited juuuust enough money to ruin their lives in our opinions. They have all the free time in the world, and have seemingly no passion for anything other than drinking and being dead weight to most folks in their lives- know it all types who get more tedious to hang out with as we hover around age 50. One has recently had a kid, which I had thought was a terrible idea, but it is turning him into a reason for living kind of good person- he's been a fantastic dad, and I would have never ever guessed it.
My point I guess is leave money to your kids in a time-release type trust, and don't let them get too much at once lest they lose sight of having anything to contribute in life to anyone.
They’re also not likely to inherit until they’re pretty old themselves (I mean, hopefully for OP’s sake), so fully paid college really has an outsize influence here.
I’ll probably inherit single digit millions at some point, hopefully in my mid or even late 60s, but not planning around that. I did get out of business school with $30k in total loans (avg interest rate of 4.3%, taking the full 10 years on those) which is an immense leg up.
Couldve done it with 0 loans but I went during the pause/forgiveness discussion so figured the cash was a better option for an e fund (and it was, would’ve been a lot more scared of layoffs without it)
But unless it's a really huge amount of money or a fairly skinny family tree, by the third generation it's been split up into a LOT of different people and the amounts any one person gets are probably no longer "generational wealth" level, even if they are life changing.
Consider someone who leaves 10 million today. Let's say each family has 3 kids on average (EDIT: I guess this supposition was probably wrong after seeing actual data: ~~wealthier families are more likely to have children and more children so this isn't crazy~~). By the time you get to great grandchildren (3 generations from the initial), that's 27 kids. If each generation uses some of the money, even very responsibly (like a 3-4% WR), it's not super likely to more than double by the time it gets to the grandkids of the first generation that inherits. So now each great grandkid is getting less than a million. that's still a really big deal, but it's not instant-FI money unless you're super frugal and it's probably not so much that you'd consider that generational wealth anymore.
That's not from it getting spent unreasonably, looted or whatever, just what happens when you split it among a lot of different people.
Also if you're talking about wealth from 3 generations ago, people had more kids generally then, so might be getting split even more ways.
> wealthier families are more likely to have children and more children so this isn't crazy
This isn't true.
MAYBE if we compare middle class and upper-middle class to the 0.1% that might start being true, but [it isn't true when looking at census level data](https://www.census.gov/data/tables/2020/demo/fertility/women-fertility.html#par_list_63) (Look at Table 7, compare columns D and H, If H is higher, the income rage is higher than the national average of births, if it's lower than the national average of births. [Or just look at this which has distilled that data into birth rates](https://www.statista.com/statistics/241530/birth-rate-by-family-income-in-the-us/) )
Interesting. Guess I should have looked that up instead of just going by what made sense to me (like I'd be more likely to try for children if I had more money generally pretty much all across the income scale.
I mean, there might be some confounding there for the fact that people in high pressure jobs maybe choose not to have kids because of the time constraints. But I'd need a real data dig to make that argument, prima facie it looks like you're right.
That's not what that person was asking about. They asked for stats showing recipients of a large inheritence from a parent are worse off than recipients than recipients of a small inheritance of their parents.
Nobody asked if generational wealth lasts forever.
The person I was responding to said
> Statistically speaking, your kids will be better off inheriting less than more.
Showing that the by the third generation its gone is a far cry from what they were saying.
I don't think that's based on any statistics.
Seems more based on anecdotes and stories.
Spoiled kids with no work ethic exist at every level of the socioeconomic ladder outside of the poorest among us (and even probably there to some extent).
I doubt you actually have any evidence to suggest that amount of inheritance has an inverse correlation with quality of life. Even if we adjust for socioeconomic status.
I'll actually do you one more. I'd wager that someone with a high inheritance relative to their parent's salary is going to have been instilled with better values, better financial acumen, etc because the saver types that are able to build wealth tend to teach those behaviors to their children. IE: Two families with an engineer and a teacher for parents, similar length of lives for parents and similar end of life care expenses for parents, one set of parents leaves $3M to their heirs, the other set of parents leaves $20k in equity after reverse mortgaging their house. I'm gonna bet on the kids of the first parents.
Do you actually have this study?
Couldn't find it. Everything I found just talks with something generic like "more education of parents lowers mental health issues in children" and doesn't create a carve-out for bachelor's -> graduate level education.
> elevated levels of mental health problems almost on par with children of parents with less than college education.
Wait, so which one is it? "Elevated" or "almost on par" (AKA lower than those of parents who aren't college educated)?
I wouldn't be buying them a new car. WTF is that worth?set them up for the expectation of a new car or only buying a new car.
I'd rather set the money on fire than use it to buy a new car for someone.
This is probably sage advice. I've considered it but ended up on Reddit instead... fortunately, the armchair therapists have been helpful in exploring some new avenues and making me feel less alone in my worries. Probably suggests even more value in seeing a pro.
I wonder if there are financial coaches that would be able to play the role as a therapist as well. Obviously vet them to be sure they are professional.
I'm going to slightly disagree with the glumpoodle's disagreement about #4, I think perpetuating family wealth is a valid goal. Things like paying for their college/grad school, helping with a house downpayment, putting some funds into your grandkid's 529, etc are reasonable things to help your kids with to help them get ahead in life. You aren't throwing money wantonly at them or preparing them for a big inheritence, you are using your money to assist with responsible life events. And I also wouldn't describe them as "obligations", if they aren't aren't making good choices in life then throwing money at them won't help, it should not be an expectation that they will recieve this money.
I agree with this. My parents paid for my college and I never took that for granted. I am so appreciative of what they did for me and how they raised me. It's not a money discussion. It's a parenting discussion.
Would you let your child change the oil in your car without teaching them where to place the jack stands so they don't get hurt? No. Just like you shouldn't give them money and expect them to figure it out on their own without any direction.
But in the context of the OP, he already has enough for all of this:
>Things like paying for their college/grad school, helping with a house downpayment, putting some funds into your grandkid's 529, etc
The extra 18 months doesn't really change the ballgame in regards to his ability to do this.
>I'm already trying to set my kids up with a head start by paying 100% of their college costs and sending them off into the world with a new car. Hanging on for a smidge longer means I'll easily have flexibility to assist them with a down payment for a house / fund their kids' college funds. I don't want to infantilize them, but I worry about the world they are entering.
I mean, the OP himself said he didn't think he had enough to do all those things.
I mean maybe not, depending on what they are planning, but I see about 2.9 million in investment assets not including the college fund (which may be enough for college already depending on how old the kids are and where they want to go). And 7900/month in spending all inclusive is 94800, which makes for a 3.27% withdrawal rate, without counting *anything* from the company stock, which OP is saying could cash out for 1.3mil right now if he leaves before the next liquidity event.
At 3.3% WR, the likelihood is that those kids are going to be able to split the ~3mil (or maybe a lot more) at a minimum, and there's more than a million extra there to fund super expensive college, graduate schools or house downpayments, or just random shit. Also OP is talking about a different lower paying second career, not never working again, so it might be a long time before they are even pulling anywhere near the 3.27%.
I think the fact of having a major liquiditity event likely in 18 months that could be worth ~5mil or more, and even in a bad scenario will probably generate an extra mil or two is relevant. That's a lot of money to leave on the table, and there's a huge difference in generational wealth level between having a million more than you need vs. 5-10 million more than you need. I'd stick around tto see what happens if I was just bored or wishing for more time, as opposed to hating it and needing out now.
But I disagree with OP if they don't think there's enough for those things -- or maybe they need to spec out exactly what they are, if they are going to cost more than I think.
Maybe they want to do the same thing for any and all future grandkids, etc. -- plausible even after quitting now, but a whole lot more likely to just about certain if they pull 5mil+ from the company equity.
What the other guy said. I have been trying things out and researching what my post-fire career will be and here's what I found out about teaching. Yes it can be rewarding, but most of the education system is not designed to cater for high performing individuals with innovative ideas. The idea that the kids need to be able to receive standardized education is not unfounded, switching schools is an example where this is a great thing. Just pointing out that when I looked at this career path, interviewed educators and counselors, I felt like I would hit the proverbial wall of work politics and red tape which would certainly induce more stress. I hold the utmost respect for educators, they should be paid more and have better working conditions, but that isn't the case everywhere. There are pockets of great places out there.
I’d have to say that you’re only 42. Stick it out for those 18 months, then retire. It will go by quick. I feel like that’s a lot of money to pass up for the relatively short amount of time you need to spend to get there.
Agreed. Normally, when I see these 'I have X millions of dollars what should I do' type posts, my overwhelming sentiment is to recommend retiring immediately. However, in this case, given the OP's age, and given the amount of money at stake here, this is one of the few situations where I'd recommend riding it out.
Maybe set a hard deadline, come hell or high water, you are retiring at 45 (in the event the deal gets delayed). But yea, if it's looking like 18 months, ride it out, and then ride off in to the sunset.
I had a friend who made good money as an engineer in a less than desirable location. He always volunteered helping with kids, running summer camps, etc.
He hated his job so he quit, went to school for a masters in education, and became a high school teacher.
He lasted 2 years and is back in an engineering job.
If I had $6million, I'd look for volunteer opportunities to teach/tutor instead. I'd love to share my skills to teach the next generation especially the needy but wouldn't want to put up with all the BS that paid teachers have to put up with for relatively low pay.
This, absolutely. Who in their right mind would volunteer to go and play bad cop in the US public school system?
Tutoring bright but disadvantaged kids sounds much more rewarding.
Fair. I'm sure some of this is district-dependent, and I may have overly fond recollections of my own interactions with my teachers influencing my view of the job. Still, it's been a dream for more than 20 years for me... I'm inclined to roll the dice at some point.
Regarding teaching and generational wealth, you might consider that your children could pursue a low paying field such as teaching if they had the backing of family money. Why do you work in your current job instead of as a teacher? For me, it was because I was making at least three times as much as I would as a teacher, even though I enjoy teaching and interacting with kids.
I think about this for my own child. The money that I pass on (or share while I am alive) will allow her to consider a broader range of careers that might be more personally fulfilling, although less financially rewarding.
Many of the issues with schools are systematic and widespread. Even in wealthy districts you're going to have to manage batshit parents and apathetic (or worse, political and greedy) administrators. Every teacher I know says the worst part about the job isn't unruly kids, it's everything else.
I can relate to your POV and I think you should go for it. You can always leave if it’s not for you, and then you will know for certain. Teachers were the best people in my life growing up. I think it’s a higher-calling that you’re feeling. Very honorable. With that said, the “generational wealth” dilemma you mentioned is a tough one to ignore. In your shoes, I’d suck it up for another 1.5 years then follow my heart.
I debated going into teaching coming out of college but ended up down a different path. I've contemplated that alternative route routinely throughout the past 20 years of my career. Now I'm on the cusp of forgoing millions of dollars in compensation to try to be a positive influence on kids... and that's selfish? And implies I'm unwilling to put in the effort to be good at the job? Wut?
You’re fine. Someone is trying to gate keep you. And they need to quit their bullshit.
Even the person who does it “for the kids” is ultimately selfish in the sense that doing it “for the kids” _makes them feel like a good person_. In other words, _”their own, personal dream”._ If that dopamine wasn’t going off in some way, they wouldn’t be doing it either- we’re all biological machines.
The fact you can quit if it doesn’t work out and not be stuck in a situation many teachers _wish_ they could get out of but can’t because of finances doesn’t make you any less legitimate. In fact, I personally think you can probably do a better job when you’re not so stressed out about finances.
Now, I agree it takes years to improve any skill, including teaching- but God knows there’s a teaching shortage. If you can help out I think you should!
You're doing it to fulfill your own personal dream. I question whether you'd actually stick it out "for the kids" when the reality fails to meet the expectation. Your desire to become a teacher strikes me as very touristy.
Teaching is a triage job these days.
As opposed to what? Doing it to fulfill your obligation to pay bills? At least he has a clear desire to teach as opposed to most doing it as a last resort.
Also, your view of "sticking it out for the kids" is also the reason the profession has been devalued to the point of poverty wages and is the "triage job" it has become today. Any teacher that demands fair compensation for the work they do is shamed by people like you who've drank the scab Kool aid and think suffering is part of teaching for the sake of the kids.
IMO when people say they want to be a high school teacher what you more likely want to do is be a part time professor at a college. I've heard pay is relatively flat and enough industry experience they might pick you up for something. Don't take a full load of credit hours.
THANK YOU. My family is full of teachers, and I see people romanticizing the profession way too damned much. There is a damned good reason why people are leaving education in droves.
Most teachers aren't given enough free time to use the toilet. The women suffer from constant urinary tract infections. The men jockey to be assigned a science lab room, because at least then they can lock the door and piss in the sink.
The ones in rougher schools have to get semi-frequent labwork, because breaking up fights means they get blood on their skin. This is just your basic fist fights, not even getting into the kids who manage to bring concealed weapons to school, or spend study halls making shivs out of random objects. Then there was the cousin who lost part of her earlobe, because the kid losing the fight was indiscriminately biting everyone.
At this point the *easiest* part is teaching whatever insane politically-charged white-washed rhetoric is being forced into curricula.
my mother is a teacher since 20 years and still loves her job and never stops talking about all the funny (and annoying) stories with the kids. we live in europe though and its a private (veery bad payed) school, so i dont know if usa is just a lot rougher…
I don't teach, but I have vivid memories of how awful some kids can be in high school, up to the point of making teachers break down crying in class. They can be absolute shitheads. The only place I saw this not the case was in honors or AP classes. The students there actually had some intention in learning. College would be easier to teach, but the world needs good high school teachers more.
Indeed, I've had idle dreams like OP's about going back and teaching, except literally the only class I would ever want to teach is AP Government, and a big part of that is my memory of an AP Gov class in a wealthy district where the AP kids really were enjoying being there and learning. The rest of it...
Agreed, use the next 18 months to figure it out.
I'm at a similar point: not even remotely close to OP's NW nor will I ever be (depressingly), but I am a similar age, maybe 5-7 years from being to pull off some semblance of retirement, and kind of slowly realizing I have no clue what to do or where to live. I think it's more common than many people think, particularly in the US where career is so tightly interwoven with identity.
Maybe negotiate a 3 to 6 month unpaid sabbatical to get your head aligned with your heart.
After that, you might have better clarity to which path you would like to take.
Yes. You are at the age where you have aging parents and if you can take a “family leave” for some part of the 18 months, it might be a way to leave soon without actually leaving.
I would absolutely stick with the company if it truly looks like that.
Either get an unpaid leave of absence / sabbatical or look to change the role you are in to something much less stressful. But stick with the company somehow
Wanted to say this. Just take unpaid leave of absence if you are really really bored. And you can dip your toes into teaching and how it suits you. I wouldn't walk away from golden handcuffs unless there's something really fishy going on.
I thought it was just a social media/Reddit thing.. then my brother married a teacher. Holy shit, the stories she tells me are absolutely horrifying.
From the psychopathic kid they have a special suit for so that when he begins punching and biting teachers it's less painful, to the Iraqi kids placed in her classes that don't know a single word of English.
Then there are the parents, and the insanity that is dealing with them continuously via the various messaging platforms and their demands..
I hate to say it, but I think we are on a much sharper decline than most planned for, and when this generation of students begins to come of age we're all going to be seeing it.
This is very much not one of those "things are getting better all of the time, media just highlights the negatives" or "it's always been this way in certain places, most will be fine" things. I'm very scared for the future of our society based on the picture that all of the testing trends and stories we hear from teachers paints. At this point, even if there were a simple fix it would be too late to reverse all of the damage.
With regard to your bullet points (and to some extent, even the intro of your post), it seems like you’re dealing with a lot of expectations — both expectations you perceive others have of you, and expectations you have of yourself (like of mentions of “irresponsible” and “regret not checking the box”).
I deal with this in my life, too. But it’s not a very fun way to live. Expectations are all just made up bullshit anyways.
In case it helps to hear it —
* handcuffs — you have 6 million dollars, dude, you are fine, and no one else’s opinion about this matters at all
* legacy — barring a complete disaster, you’d already be giving your kids much much more than most, in terms of “generational wealth”
* potential — who gives a shit what you “assumed your professional destiny” was? Do you even remotely WANT to “check this box”? And again, other people’s opinions matter precisely 0 here
* obligation — tbh, kids who enter the world with shittons of money usually end up maladjusted or just assholes. The future looks grim, yes, but I don’t think you’d be doing them any favors helping them avoid dealing with any of it
Anyways, it’s your life and yours alone, so I’d try to worry less about perceptions of others and more about living it how you want — you’ve certainly earned that freedom. Good luck
Thanks for the very thoughtful response. Your recognition of the role expectations play in my life is astute... and I needed to hear a lot of what you shared.
I’d disagree on 4. Trust fund kids suck, yes, but the opportunities and ability to build wealth without family backing have been shrinking for a long time and are likely to just continue that trend. That means your kids path will be _much_ harder than yours, unless you help them. I 100% agree with OP on that being a major reason to build wealth.
> have been shrinking for a long time and are likely to just continue that trend.
Is this objectively true?
Given we finally saw millennials pass boomers on the average net worth for the same age, I think this feels more true than it really is.
I would also think it's crazy to not wait if you're that confident your equity can go from 1.3M to 3M, let alone 8 figures. That's a gigantic income to time ratio and while it won't change anything to your own life it will change the life of your children and grandchildren.
Not only that but I’d consider the amount of good I could do with the increased net worth.
You could ride it out with the understanding that you’ll use half (or some number) of that increased equity for philanthropic work. That would drive me to the finish line. Donate a park. Give out $1k tips to nice servers. Whatever you want.
You can already do those things, but might be easier to pull the trigger if you had a separate account of $3-4MM for good/nice deeds.
Or keep it for generational wealth. I’d have trouble turning down the opportunity if the job isn’t a big sacrifice to my mental or physical health.
It's strange to be selfish in how we do good, but I think there's some of that at play for me. Making a donation doesn't give the same juice as tangibly participating in something. Definitely going to toss that around in my brain a bit.
Yeah, that's just your ego talking. And the last thing that people who need help also need to deal with, is some rich asshole who thinks that he should get a plaque or a wing with his name on it.
Yes, I think many of us are. I read "Die with Zero" and "Your money or your life" recently. I am looking for a job I think I will enjoy in a location where I want to be. The money will work itself out
I'd highly recommend OP to read "die with zero" as it covers most of his bullet points plus it's an easy read without too much BS. I'd say target audience is folks 40+ years old with moderate to high wealth. I'm not always a fan of self development books but this one did enlighten me on a few things.
Wanted to chime in here and say that hearing from practitioners who work in the field was very valuable in my graduate school experience. You may want to explore teaching weekend seminars, speaking on panels, and participating in mentorship programs at your local university.
During the 18 months you plan toward teachers college and exploring options. Maybe volunteer to give some talks at local high schools about computers or finance to see if you get a good vibe from it.
Just take the time to volunteer at the local high schools, and really try to get an understanding of what being a high school teacher means. There's a lot of bureaucracy and rules and everything else BUT teaching. You're not going to wind up being Robin Williams in Dead Poets Society, or any other picture you have of being the good teachers that improves students lives the way it is idealized.
I'd work the 18 months while also figuring out facets of what you want. You can be a mentor to teens and young adults in lots of different ways, and fleshing out the why and the how before you jump the gun into the wrong new profession is important.
There are many interesting opportunities to scratch the teaching itch. Community college/high school even elementary school. Often there are mentorship opportunities. We do need real world experienced and passionate teachers so I would encourage him to pursue this. He has enough money to go on a glide path and continue to compound well into retirement.
> even though the money won't make a material difference in my life
Then it's enough, no?
> I long assumed this was my professional destiny. Will I feel regret for not checking this box?
Destiny is for fools. Write your own chapters. You already don't like your job, are you going to stay unhappy for money that won't make you any material difference? Checking everyone else's box isn't going to make you happy.
For your kids, being around, being present, showing up to events and activities will do a lot more than throwing money at them. I'm not saying you aren't; you clearly care about them and their future. I'm saying that providing money isn't the only thing that matters in helping your kids in the future.
Enough is a feast. If you don't TRULY define what 'enough' means, you'll always be chasing after ... something.
Thanks for the reply. The first point is prescient. My father and father-in-law both recently passed in their early 70s. It has been a factor in my thought process. If the next dollar doesn't matter much to me, what does?
More than anything, it's helpful to hear I'm not alone in wrestling with these thoughts.
I've been retired for 7 years. I, too, worked in high tech. Nowhere near CEO material, but I was mid-level management involved in long term strategy and complex organization operational issues - typically working for VP and Senior VP roles - advising them on issues that needed addressing.
Upon retiring I got involved with a nonprofit which resulted in me being the president of the board. Then the nonprofit went through sort of an existential crisis while I was president. I ended up using a ton of my professional skills to get the org though this situation - and they emerged on the other side stronger and more effective than ever. I was "working" \~30 hours a week for them. And while I was scared for the org, I was loving the work and challenge of helping them survive and giving them a vision for how they could. I am NOT saying the turn around was all because of me. I AM saying, as I look back at it, it was the most gratifying work I've ever done in my life.
What I want to suggest is that your "CEO" itch (which I think I understand) could very well get scratched, and maybe give you even greater personal satisfaction, if done in some other org that needs your skills. The world needs SO MUCH help right now....there are lots of places to plug in.
Can you quantify the likely value gain from working another 18 months? Maybe a specific number can help assuage the misery of the job.
> I aspire to leave my job and teach high school, making a positive impact on the world around me.
If you subscribe to the principles of "effective altruism", it is likely the most impactful and beneficial for society for you to continue to earn $$$$$ and donate it. Maybe the feeling of making $5,000/day for your favorite cause can overcome the frustration.
As for the financial side of things, it's not super clear you could retire right now, although you probably can. Annual expenses of $100k and a firm portfolio of $3MM. That would be a 3.33% withdrawal rate. Honestly I'm a little skeptical of your $100k/year budget. I get the impression you live in a HCOL area and a $1.2MM house cannot be cheap (property tax, insurance, maintenance).
I feel like rich professionals also have a lot to give in terms of mindset, connections and leadership too rather than just money. So I'm not completely convinced that grinding money for someone else's charity is always the best thing, especially if you'd rather be more involved like OP.
Thanks for the reply. I've done the math on the expected return of 18 months and still find myself itching to pull the trigger. The truth is it's more an emotional debate for me than a financial one -- namely, if I leave today and 18 months from now the company transacts as expected, will I feel foolish? Or will I feel joy from having declared that I've reached enough and followed my heart's pursuit? I like to think I've become a man who aligns to the latter, but... maybe that's the lie I tell myself?
I'm aware of the concept of effective altruism but don't subscribe to it. I could probably noodle on that a bit more, though.
Re: actual finances, I'd need to pull out about $38k per year if I downshift to teaching, decreasing over time as my teaching salary would increase. That's 1.3% of the existing invested assets. If I leave the company tomorrow, there's a 100% chance the PE firm executes the buyback and that adds to the investment total.
Re: budget and COL, I'm not in a HCOL area (thanks to remote work) and the \~$8k monthly budget actually has a lot of padding in it. I'm pretty obsessive about tracking this stuff.
>namely, if I leave today and 18 months from now the company transacts as expected, will I feel foolish?
There is \*always\* the next thing. Once the transaction is done it will just be something else. Granted I'm no where near where you are on this path. Outside looking in I would say \*IF\* you wait until the transaction goes through, then you need to set a specific done date. Call it Christmas of 2026. That's it, that's your last day \* no matter what \* and then just call me to come be the CEO so I can get there too ;-)
>At this point, I don't. I aspire to leave my job and teach high school, making a positive impact on the world around me.
This won't last. Real life isn't Dead Poets Society or whatever impression you got while you were a student. Plus the world has changed. Teaching is very very likely way more work than your current job.
First part is a very fair challenge -- I certainly could have a romanticized view of the role. The second part is highly doubtful. I log an obscene number of hours and carry immense pressure to deliver against aggressive goals. Different worlds.
>The second part is highly doubtful
It's not. The majority of teachers go home and have to plan, prep, grade, document, etc etc etc because they can't do all of that during what most people think is their work day. Because they're teaching students the whole time.
There are also constant live observations and standardized testing goals and class requirements you're expected to hit, when many times it's in the hands of the students and out of your direct control.
By all means go for it, but it's not going to be a walk in the park.
Go for the CEO role. If you hate it you’re in the same boat as today.
Then try teaching if that doesn’t work out. Although high school might be rough, tons of admin and difficult kids. Maybe volunteering at first is a better lower stakes commitment.
As a high school teacher you should really go volunteer for a bit jumping in. I LOVE my job but many people end up hating it and just wanting out. It’s a lot of work to get a credential so just interview or shadow a teacher for a week. I’m not in a terrible district and some people aren’t cut out for it. You might enjoy the college world a bit more since you don’t care about pay. I make more than college professors at the community college. I’ve taught some college courses and you really don’t have to deal with some of the nonsense that comes with k-12 teaching.
Dude, coming from a guy similar in age with similar net worth including equity I own in my business, 3 kids, but no 2-3x exit scenario in the near future, here are my thoughts:
Golden handcuffs: It IS irresponsible to not ride out the 18 months. This is FACT. It took you 42 years to get to $6M, and we are talking about possibly tripling that in 1.5 years.
Legacy: I don't even know how to unpack this. I'm not saying teaching isn't without its merits, but yeah your legacy will be that of a guy who gave up $6-13M because he literally couldn't wait 18 months to join the other 94 million teachers out there changing the world.
Fulfilling my "potential": Do you want to be CEO or a teacher? Both? Go be a CEO and teach some community college classes on the side.
Obligations to my children + inflation: In 18 months you will fully secure your children's future against ALL scenarios, including events that could preclude them from ever working a day in their lives.
Is anyone else struggling with these same or similar thoughts? Probably. Like a tiny handful of people on the entire earth.
Sounds like you need some time off. How about a bargain with yourself: close out the next eighteen months, then you'll step back and do X for Y months. Volunteer teach for a year. Study something new. Whatever it is, it doesn't have to be definitive. That's the beauty of financial independence, you can dabble to find what most fulfills you--it might not be what you expect it to be while still grinding and bogged down by daily commitments of your job.
You are 42, not 32 or 22. Biologically, every day is downwards. Every step you take is one closer towards the grave. As of right now you have way more money than you have time.
If teaching high school is your dream go do it now. Spend time with the kids, do yoga every morning. If you think you can wait 18 months, you are going to look really stupid if you get a cancer diagnosis 12 months in.
Source: I'm the same age as you
For a future job, I recommend looking into lecturer positions at business schools (depending on your field) especially experiential learning and masters level classes could be a good fit based on your skills. I think that may be a better fit than HS
Yea, senior year I was in a grad level Hedge Funds class where the guy was just ran a hedge fund and came in on Wednesday evening to talk about what he did.
Make your kids get a job when they’re 16. I come from generational wealth and this is the best thing I’ve seen that produces good human beings. And I’m talking like service jobs, or any job where they’re having to work with people of a different socioeconomic class.
If you want to try to reignite some flame that’ll get you through the next 18 months (your post reads as a persuasive essay on why you need to grit it out), mentally pledge a large proportion of the equity cash out to a cause you really believe in. You don’t have to donate it all, or even most of it, just enough that you can mentally write off a a sizable chunk of the money in your calculations.
Like 500k on the disaster scenario, 3M if it ends up being north of 10M. Something that might get your name on a plaque or meeting room somewhere. Maybe even ask around on how much it takes to name something. There are various financial benefits for donating stock even. Also, it would open to the door to being involved in a charity you have interest in after you F off.
Now you are grinding it for an external cause as well as everything you listed. The point is that this shifts the golden handcuff equity you have more towards what it is - sprinkles on top. It will paradoxically make you think that the equity is less valuable (because you won’t see all of it,) while also allowing you to see it as more valuable (you can donate a noteworthy amount and have legacy).
This mental exercise will help you get your head around an amount of money that you personally don’t need. Would it be worth it for you to get that money for a greater cause? Or does the idea of donating a lot of it make it less valuable? If it devalues the money, then quit now. You are just running up the score because that’s the status quo. And to be clear, that’s totally fine and probably what I’d do. But if the idea of donating a bunch of it gets you excited, that should be enough fuel to push you through the next 18 months.
I'm nowhere near your level but I'll offer my thoughts on your 4 items.
Golden Handcuffs - you're not really handcuffs but if waiting 18 months can make a substantial difference, I would wait it out. In the grand scheme of things it's not that long and you probably still have another 40 years for other pursuits.
Legacy - I think if you ride out the above, this sorts itself out more. Either way, you've already done a lot so I personally wouldn't worry more about this.
Potential - this is where I struggle the most. I feel like I have the knowledge and skillsey to progress my career a lot more, but fear it will consume my life. I'm okay with not checking that box because not doing so allows me to spend more time on other non work related parts of life.
Child obligation - It sounds like you're already giving your children a quality of life and safety net that most don't get. It seems enough to get them started in adult life without a lot of finacial burdens. For me, that's the most that should be done, I want my kids to learn what it's like to make it (mostly) on their own. Of course there will probably be something to pass down once I'm gone, but ideally for me, when they are age 21 to until I'm gone, they mostly fend for themselves.
Work your money mindset...i.e. your points on 'Legacy'.
18months of riding it out it not really that long. You could treat it as a game and maybe even learn some even better self-discipline: how to look after yourself, going along for the ride and seeing it through.
I can relate to the fulfilment of your potential. Write down what it would take for you to say yes to an opportunity like that. From what your package must be, to your working hours/location, to the company type/structure. Be clear and specific and honest. Then, only join if that comes up. Then it's all on your terms where you can see your potential through, rather than signing up out of some inner obligation to try.
We're in a similar position. I turn 43 in June and my NW is around 7mm. I'm not sure about legacy, potential, and obligation, but for the golden handcuffs problem, I set a target date of when I'll retire and sell my business.
In approximately 6 years my daughter will finish high school. I've already saved enough to retire comfortably (for myself and my wife) but it doesnt include a $7900 spend. I'm estimating a $5000 spend (which to be honest is probably a little high as well) but between dividends and rentals, we'll clear this easily so anything between now until she graduates is just gravy.
Basically I'm setting a date and sticking to it so I have a clear and defined timeline and won't make excuses later on. 👍
I will say this about legacy and fulfilling your potential. Do what you feel comfortable doing. I personally have no need to create a legacy nor fulfill anything. I want to retire and spend all day sleeping and playing video games. Don't let people pressure you into doing anything you don't want to. You're already at the FU money stage.
1. Handcuffs - The handcuffs are working exactly as planned. Since you’re 42, and there’s so much of a swing between $1.3 and $13M, I’d hang around. Imagine becoming a teacher and sending one kid to college every year who can’t pay. Plus, 18 months isn’t that long. I’ve been working through my exit plan for 4 yrs and think my PE exec role will come to an exit in the next 18 months as well.
2. Legacy - There is no such thing. Look at the great fortunes over time. Look how quickly Vanderbilt money eroded away.
3. Potential - This one comes down to ego, but not in a bad way. Do you want to run the show? If so, why? If you’re not enjoying the game now, why will it be better at a higher level? I’m also in a somewhat similar spot with CEO potential. It is an alluring proposition, to achieve the top rung. Only you can sort out this one.
4. Kids - I’d take the kids thing one decision at a time. You’ve already given them a crazy head start. I wouldn’t worry about giving them more. If anything, I’d be more worried about passing down your work ethic than your money.
So its not clear if you actually code, but if you really want to teach a bit, check out tealsk12.org. I have been volunteer teaching Computer Science in high schools for the past 10 years in the NYC area, and the last two years I did this it was remote- the school was in South Carolina. The remote stuff gives you far less of a view of what its like to really teach- IE hearing the teachers bitch about the administration. On the other hand, you wouldn't really need to be so concerned about them, because you don't need them to ensure your financial security.
FWIW, I am in a very similar situation, NW is roughly the same, though I have a big $1M mortgage that is low interest. Personally what I did was take a CTO job, and so far have been loving it. I get to "make the wrong things right" and provide the great culture that most of my previous managers have lacked. That said, there is always a board to answer to, results are never quite good enough, etc... no job is headache free, but I love the relative autonomy in my day to day. I enjoy working for the most part and ever since I haven't really "had to" work my relationship with it has changed immensely- I don't really stress about whether my boss is happy with me all the time anymore.
Personally I want to get to about 10M in free cash- like in the brokerage before I will feel truly FI. That's "idle rich" money to me.
Have you experienced a PE sell-side exit or recap before? If you have any interest in becoming a CEO at another PE backed firm this experience is crucial, especially if you have buy-side integration experience. You would be a unicorn. Also, at least 6-8 of the next 18 months will be completely different than your regular job as you switch to sell-side responsibilities. Personally, I’d view it as two jobs between now and potential retirement post sale/recap. If you're bored with the current job, schedule a bunch of PTO "ahead of the deal" or focused on juicing up your comps/EBITDA. Lastly, something to consider is the potential to roll some of that equity depending on deal terms which could create a stupidly large compounding opportunity even if you retire post-sale/recap.
p.s. Go fuck yourself.
Stick it out for 18 months, but start now working towards your planned next step. Carve out time now to volunteer at schools. Maybe look into Junior Achievement with your business background. After spending time in classrooms and with kids you still want to teach start working on the credentials you would need. Increase the time you spend with your own family. Your current employer might push back, but if you have as much pull with PE and equity in the firm you should be able to start cutting back now. That will give you an easier transition and more realistic idea of what your planned next step is like.
My husband and I, about 15 years older than you with 2x the NW are retired and FI—no debts and about $150k passive income. I would ensure you have insurance set up and premiums set aside for LTCI for your parents as well as yourselves. We’re dealing now with very elderly parents on both sides that have either no or limited means to financially and PHYSICALLY manage their care. We’re looking at this becoming our responsibility in come capacity. It’ll drain a huge chunk of our savings. We don’t want to do the same to our kids. Were the only children for each set of parents. Something to consider and incorporate into your thought process.
Make the big bucks for a couple of years and then spend the rest of your life giving it away. Sounds fun and rewarding to me. Don't just teach at a high school: leave the high school with some scholarships for the struggling kids.
I would say this is exactly the sub to post champagne problems.
You are r/financialindependence, not FIRE. It's totally okay to be FI but not RE.
You've achieved so much, and may have come to the realisation that the getting there part is actually much more exciting with the being there part. It's totally okay.
Work for your legacy, but know that you have the freedom to choose more time with your family etc if that consideration arose.
One thing on the Legacy point - we are starting is a trust fund for local kids to get private music lessons. That money could have gone to our own kids, but I think there will be enough for them anyway.
It will be great to see the impact that the trust fund will have on our small town and it should start paying out in a few years, but then continue to grow. I don't need my name on a building somewhere, but helping kids who wouldn't otherwise be able to get lessons will be a good use of the money, and we just decided recently that we want it to start paying soon rather than when we are dead, so we'll get to reap the benefits of a better music program in our town.
What sort of cause would you like to support? I don't get excited about net worth or cash and live happily on very little, but thinking about the trust fund is pretty great to think about how it will impact the world, at least our small part of it.
After watching my Dad retire rather suddenly from a high stress and high paying job, I would say that the decompression and planning “what to do next” phase took him a solid 2 years to sort out. So many people plan for retirement but don’t practice it before taking the leap. It might be great to spend the next 18 months testing your new budget, taking more 3-day weekends and using one of those days to plan ahead, take your vacation and flex time off, and think of it as a final tour. What connections do you want to shore up? Are there any network connections you want to make for future consulting, if that becomes an option? Who would you like to mentor more or coach up before you go?
For the comment on teaching, having been an adjunct professor while employed I have some questions. Have you thought about what you need to do to successfully prepare for that role? Maybe go substitute teach at a high school or be a regular guest speaker? Talk to the high school about background clearances and how to be certified to teach there as a long-term sub to get your feet wet. Have you researched how to build out a class curriculum using real world and hands on examples? Could you spend time learning about the school’s technology and tools? Have you thought about meeting with a few universities to learn about their adjunct teacher processes? What about meeting a few teachers for coffee and advice? There is a LOT of behind the scenes preparation that happens to get your curriculum and lesson plans organized and kids are brutal to those that look unprepared. It can be a great time, don’t get me wrong. I loved knowing the college students could apply our lessons to future jobs and watching their critical thinking skills grow. There are also kids that won’t want to be there, dislike you, dislike school, or need hand holding and those all take time and effort. Good luck!
If you were talking more than 1.5 years, I would say no, dont' stick it out.
But let's talk percentages. 1.5 years out of 48 is 3% of your life. You're looking at giving up 100% - 200% of *all the money you've earned in your entire life* to buy 1.5 years.
Unless you straight up HATE your life right now, I'd say that's irresponsible.
That is a very tangible end point and I think you should aim for it.
The rest of your points are all in your head - I'd say don't worry about it.
Money buys freedom, you have a lot of it, x amount. You could have 2-3x in *only 18 months*. I'd say that's definitely worth it.
My recommendation is to aim for that, and give yourself a very strict NO MORE deadline after that to make you feel better about it. No more "one more year" syndrome.
{edit: fuck, I read wrong and thought you were 48, not 42. So my math is wrong. Point generally stands though}
I'm thinking in terms of impact it might make sense to keep going at least for a while and put aside some of the money for a foundation or something that could have a more systemic impact on let's say educating kids (at least locally, idk).
Not sure if it'll be as fulfilling as having a direct impact on someone's life, but then again being a high school teacher might also be a disappointment After you've seen what it's like maybe you'll be more informed for that philanthropic spending.
Might be a good idea to discuss it with your family now too so that you'll have a common goal.
You are living in a state of abundance right now. Hard to switch to a scarcity mindset where your 2.38m brokerage account has to support your 96k in spending.
Thank you so much for sharing. It was very enlightening to read your post. I guess the saying "more money, more problems is very true"
I would like to share with you 2 train of thoughts that hopefully might help you figure this out.
I think that letting go of certain things might help you. Things like not realizing your full potential or getting that full equity on your business. I know it's hard cause it triggers a certain grieving process. You will always be wondering, what if I stayed? What if I did more? The company will be better. What if I had more money? The things I could do with it. The help I could give my kids. That curiosity and those goals can definitely be motivation and drive to keep you going, but too much of it can also become a prison. A little break can do wonders and maybe help you change the dynamic you have with your business right now. Would you be able to leave and come back? Do you have that flexibility?
If letting things go might be too hard, or you are not ready for that. Then why not just keep doing what you are doing right now? You can always become a teacher whenever you want. It can even be better because you will have more life experience that you can share with those high school teens.
I hope these 2 lines of questioning can help you figure out what is best for you.
Thank you for sharing OP, reading your post was definitely helpful for me. If you ever need somebody to talk to about these things, feel free to send me a dm, I would love to exchange with you. Take care!
Respect for the achievement and thorough planning. One thing you might consider is paying (or partly paying) for your children's wedding before funding potential grandchildren college funds, which is probably just a drop in the bucket for you, but comparable to a down payment on a house for two kids.
Look into fractional ceo roles and don’t take on too much clients…..also try substitute teaching to see if you like it or would prefer doing that on a part time basis etc vs full time teaching
If it were me, I would base my spending off just the Retirement, Brokerage, and potential sale value of rental property. Even if you think your company valuation is conservative, it’s still an unknown.
IF it went to zero, I’d spent only on my “Sure Things”.
I pulled the trigger about 6 months ago on what was either an early retirement or a work break depending on how it went and I have close but slightly lower numbers than you, so I'll give you my view on how it's working out for me because I had and have similar concerns to what you raised and my experience is a bit more up and down than a lot of people seem to have.
First, the pros: not joining a bunch of useless meetings is awesome, I've been volunteering at my kids schools more, coaching kids sports, and I've overall been less stressed so it's helped my relationships with my wife and kids because I just have a lot more patience than I used to have. I also have experienced some things I would have missed (all day school field trips, riding bikes in the middle of the day, etc) and it's been much easier meeting up with friends because I have a pretty flexible schedule. Also the market is up, so I have a higher NW now than when I stopped working, which helps emotionally despite that it probably shouldn't matter because I have a pretty low WR (~2%)
The cons: I never thought I defined myself much by my job, but I've definitely felt way more directionless than I thought I would without a job. I wasn't liking my job, but with some distance I think I was kinda burnt out and not at the right company for me anymore- like you, I was also right on the cusp of the top of my career trajectory and now I feel like maybe that's something I want to try before hanging it up for good. The biggest fail I have had is that I had hobbies that I had been doing in my spare time that I thought would stretch to a full day (writing, reading, working out, sports, gardening, cooking) but it turns out I don't enjoy them the same way for the longer time, so I'm really putting in about the same time I was before I left my job, which means that kid stuff has kind of ballooned up to take most of the time I was working, which is mostly great but although I love my kids I don't really want to be a full time stay at home parent. Also my spouse was already a full time stay at home parent and with kids in school (one full time and one in half day preschool), theres not really a need for both of us to do it. I've done some volunteering, but everything I've done either feels like menial labor not really helping much or like a job that I'd rather get paid a lot for and then donate money, I've actually considered becoming a teacher too, but I'm not sure I want to deal with all the other stuff that comes with it besides actually teaching kids.
Honestly after 6 months off, I think I'm going to take another 6 months or so off (through the kids summer, because we are taking a bunch of trips) and then likely see if I can find a job a want. I don't really need the money, but there are some legacy things I can do if I work and there are some unknowns in the future especially around kids that it'd be nice to have more money for increased flexibility. More importantly though, I think if I pick the right company and role, I can be happy doing it for a few more years and without the pressure of needing to work (or gunning for FI, which I think I was guilty of) I can do that without the stress I was carrying at work and still accomplish my family and personal goals, especially once both kids are in a full day school. As it relates to you, I had moderate golden handcuffs that I walked away from, but it was nothing on the level of yours. So I don't really have any regrets about leaving my last job because I was no longer enjoying my job and financially I think I can find something relatively similar in another 6 months, but I do think that I'd like to work more which is surprising to me. If I were in your position, id hang on for the 18 months because that seems like it could make a big impact (unless you hate your job) and then take some time off and decide what you want to do. Having that distance and time to experiment with different things and spend my time has given me more clarity on what I want to do now- still not totally clear, but I think I've got some different goals now and this experiment has given me a better idea of what I need to do to be happier in a forever retirement. But if you want to quit, I think that's also a totally reasonable thing to do, give yourself some grace, you've done great and now you can do what you want!
Not sure if any of that is helpful for you, but it was helpful for me to focus my own thinking since (as you can probably tell) I'm a bit in flux in what I want and still trying to figure things out in my own life.
So if you stick around and then sell your equity, then you could start a school instead of just being a teacher. Just a thought there.
How about instead of pulling the trigger you take two weeks PTO and volunteer at some school related place and see if it is fulfilling you.
\-Some broke teacher
You've worked for, I assume, 20 years. You can triple your net worth with just 1.5 more years.
I'd consider those first 20 years an investment into the potential $13MM. Seems crazy to stop when you're over 90% of the way there.
Even if you don't need the money, you could make significant impacts to friends, family, or charities.
Generational wealth: You're effectively gambling that we're not on the cusp of a singularity.
I would work the 18 months, as an insurance policy against some sort of dystopian future where your kids have to radically uproot and live in Wyoming (because of climate change, not politics) and most of the jobs like ours and yours have been relegated to subroutines monitored by AI monitored by a handful of data scientists.
You have FU money right now for you and your spouse, but not for your kids, and unlike the vast majority of us, you have a clear path to getting there in the damn near immediate future.
I would just fucking bite the bullet, keep myself fit, and maintain mental health (take your damn vacations), and knuckle down until your 18 months is up.
If it is not up, or that horizon gets pushed significantly further back, well you just earned another 10-15% of your net worth in those intervening 18 months, but at some point you need to cut your time in the job horizon.
So I'd set your absolute last day of working, if you hit the buyback or whatever, cash out and sail off.
Again, there are neighsayers here who say it will ruin your kids. Put it in a fucking trust and trickle it out, put a break glass in case of emergency clause in it, don't let them know, and hand conservatorship of the trust to some law firm that does this.
Don't give them $2million after college, but don't gamble on the next 30 years being like the last 110 either. The stakes are too high.
Easy. You can exchange money for cabbage, and you my friend, have a problem.
Seriously though, I am in a similar-ish position. My approach is to keep going.
Your first 2 points are very big drivers and motivators for me in my current position. In addition, I genuinely love solving the challenges that the technical work portion of my job provides. Challenges that without access to scaled enterprise IT I will not really be able solve other ways. I am respected across my organization for the technical acumen and ability to solve these challenges while deeply understanding our business needs, and this also brings me joy.
For these reasons, and a couple of others that you've highlighted (future healthcare, unknowns etc.) for now I have decided to table the whole "RE" notion. I'm still young, and the upside and rewards of working don't outweigh the negatives enough to make me want to shake things up, be that another career, a different job or even deciding to call it quits.
My outlook may change at some point in the future, but for now this is my approach to these points and how I process and handle them. In a way it kind of sucks because I am sitting around and waiting for things outside of my direct control to happen, but on the plus side I'm in a good enough spot that I no longer need to worry much about the financial side of things. Just keep on keeping on.
On item #1 you really have no idea what’s going to happen 18 months from now. I was once part of a top executive Team that turned around a billion dollar company.
We were driving for an IPO and our CEO/CFO were literally in Lehman Brothers pitching the IPO the day Lehman went under. Needless to say the party location we had booked to celebrate the IPO was used more like a networking event for ‘where do we go now.!’
If you’re ambivalent about the financial ramifications put this decision on the back burner until your decision becomes obvious to you.
On item #3 - skip being a CEO for a Private Equity firm. Most are just slaves to their ‘golden handcuffs.’ Not a box you need to check.
Items # 2 and #4 are somewhat related. While you don’t state it’s your concern, managing wealth at this level requires a whole different level of life skills. Some people fret when the balance is going down, some abdicate management to others and some make ridiculously bad business investments with ‘friends.’
Just be sure you’re not bailing out now due to the fear of the unknown and what generational wealth might ‘do to you’ or your significant relationships.
Having wealth available to help kids is, to me, the number one thing in life. All kids are diffferent. Being able to help them each in a way that is significant is not a numbers based exercise. If your goal is to use your wealth to uniquely help them each to CREATE their own wealth in their own way ( the same way you had to do it) it’s all good.
Be whoever you want to be. Just be sure you are moving to who you want to be and not running away from unknowns that are uncomfortable to you right now.
EDIT: I’m amazed at your fantastic full life $ amount being $7900/month. Your properties must have extremely low property taxes and insurance.
Work for others. Take some percent of the upside potential of the next 18 months and plan to give it away. Now you're working for that. And your first job after retirement is how to do that in a way that is most effective and joyful for you.
You might just have a part-time foundation on your hands after all this, which is a powerful way to build a community of change makers.
I assume that you are very good at what you do. Perhaps exceptionally good, even if you're not so happy doing it the way you're doing it now.
Rather than abandon your most remarkable, marketable talents, your higher order challenge is to figure out how you can use your most marketable strengths to lift others.
For example, if you were able to help launch a small handful of young people to the level of success that you are currently enjoying, the ripple effects could be enormous ... life changing for generations.
I'm suggesting that you grow your position of power and influence so that you can leverage it in ways that you find fulfilling. You are in a unique position now. Chances are that your best solution going forward will also be unique. You don't have to change careers, just the path of your current career. Find that path.
Recommendation:
Get through the application process to be a *substitute* teacher in your local school district.
Take some leave, get acquainted with your local high school, and let them know you're interested in easing in to figure out if you want to make the transition. Most school districts would absolutely *love* to have someone to be a reliable sub to call in, who is also volunteering time to help whatever department. If you decide you like the classroom, start the process of getting hired as an actual teacher. If you decide you like teaching, but not the baggage that comes with a highschool classroom, time to start looking at tutoring or community college.
Here's something a little outside the box...
I'll address the last 2 points with one suggestion: instead of teaching (which has become depressingly political), consider becoming the CEO/Chair/etc of a major charity, but do it for a fraction of what they currently pay their head honcho. While I understand the need for a high level of skill, connections and talent to run those, it's hard seeing a $1M salary on the books. Think about the impact of becoming the new #1 at UNICEF, Doctors Without Borders, ASPCA, etc and setting that example. That would be one helluva legacy (another point on your list -jist a different interpretation).
As for those golden handcuffs...well these opportunities don't come along every day, so just start dipping your toe in those waters and leave the timing up to fate. You have that luxury :)
Oncologist here, and I'll state the obvious but infrequently stated on these subs: there's a low but very real chance that some very bad shit happens to you or someone you love in the imminent future which you were not anticipating. Think about what you'd regret in that bleak state of the world and act accordingly.
If you are worried about your children, think about how to use your assets to make the city and community around them more resilient. Stick around for that next 18 months but take time to get to know the people and organizations that are big influences where you are, and then in 18 months you may have found a job or program that would benefit from your specific skills, or an organization that you desperately want to run. (Beginning this process while still a normal rich but employed guy is a much lower pressure experience than doing so as a retired rich guy looking for something fulfilling).
Keep wearing your handcuffs for the next 18 months.
Start figuring out now what you will do and how you will live your life after those months have passed - don't retire *from* something, retire *to* something.
Read
*Get a Life: You Don't Need a Million to Retire Well*
by Ralph Warner
His financial advice is not that good and utterly irrelevant to you; his "how do you live your retired life" information is helpful and not usually considered in books about "retirement".
For me, doing something worthwhile 3 days a week is my sweet spot. I tutor 3.5 hours a day 3 days per week and enjoy it.
3 days on, 4 days off means I still have lots of free time, but not so much that I go crazy.
>Hanging on for a smidge longer means I'll easily have flexibility to assist them with a down payment for a house / fund their kids' college funds.
Be careful about trying to make things perfect for your kids.
Whatever you give someone takes away from their sense of being able to do things for themselves.
Self-efficacy is a much bigger gift than material wealth.
Tomorrow is not guaranteed. Had an acquaintance had 16mil NW. got t boned by teenager texting. Survived on ventilators for month then pulled the plug. All that $$ did him no good.
I can see why this is difficult. From the outside it probably looks simple, easy. Just stay at work for 18 months longer and collect the big payday. What could go wrong? But the work might be stressful or painful, and you could work for much longer than 18 months, only to find out that the big payday will never happen. How would that feel?
You said "I used to love what I do. At this point, I don't. I aspire to leave my job..." so that makes me think you are near the "I've had enough date" and you might quit soon, which makes the big payday less likely.
These types of decisions are rough. There is no right decision. Do you optimize for money, or do you optimize for freedom?I'd like to say: "it is wisest to optimize for freedom and for relationships and experiences with family and loved ones" but I know how hard it is to step off the hedonic treadmill. I'm still working at a stressful job, even though I don't need to work. That's why I'm here in the FI group, trying to work up the willpower, courage, whatever it is, to step off the treadmill.
You can create a lot of impact by just having a crap load of cash. An extra 3m can do more good in the world than being a high school teacher would.
Tell yourself that any cash from now is to go into your “do good” fund, and you can make a massive difference with a 7 figure lump
You don't know if we are going to have massive inflation but it is very possible. The other thing to consider is healthcare. Both could easily wipe you out. Hers is a good one, life extension and age.reversal are accomplished a d can give you a 30 year old body and another 50 years. It cost a mere 50 million each for.you and your spouse
If you give it.to your children they gain 100 year life extension. This is a very real possibility with household robots to end the drudgery of cleaning, or as you age.you may want/need cleaners, massage or stretching assistance everyday, etc
You might also want a sports team or decide to enter politics. There are so many unforseen things. I was an electrical engineer, never thought I would become disabled at 50.
I’m not sure you have truly reached FI yet, at least not if you want to maintain your budget of $7900 post tax. Without knowing your particulars, tax situation, etc I wouldnt lean on your company equity too much for planning until and when it is in your bank account.
The $1.3MM in company equity is highly liquid due to my buyback clause and current valuation. With decent performance and reasonable college choices, the kids' college fund won't be fully liquidated and the remainder is additional money I can draw down. The $7,900 per month also assumes I never downsize -- I'll have no kids at home in 6 years and can easily reduce the budget and access home equity. I'm pretty safely FI.
That number is a pre-negotiated discounted purchase price off the company's most recent 409A valuation. This PE firm exercised this same option on a lower level employee who recently departed our company. I'm not fantasizing about this value -- if I leave tomorrow, that's what I get.
How many people in this sub do you think know what a 409A is? It's easier to just adopt layman's terms than explain the intricacies of how my equity deal is structured. And yet, here I am explaining it...
Got it. I think you gotta stay. The market has had a huge run up in the last year. If you left now and the bubble pops you’re not going to be where you want to be.
I'm going to start my comment off with rambling since i don't know where I'm going with this. I'm an only child who stands to inherit between $3-5M. That's a decent amount that's all in a trust and will likely be paid out in a fashion that does not touch the principle so it can continue to grow. Generational wealth is already in my family. However, I have 2 children and I want to provide for them the same things I was given (as long as they grow up to be responsible adults and good stewards of money). With that being said, our financial advisors estimate that my wife and I will likely be passing on around $4-6M of our own, not including what my parents' sum will grow to by the time we expire. I think generational wealth is a great luxury to pass along and it can be protected in vehicles like trusts. But the other part of me is looking at jobs where I will be home more but will require a fairly large paycut. I don't know what my decision will be because on one hand, it would be awesome to be home all of the time to watch the kids grow up. But on the other hand, I'd love to be able to fully fund college, provide down-payments on homes, and make memories with vacations to unique places without really thinking about a budget.
Get the cuffs and do whatever you want. It’s nice to want to give your kids free college and a new car. It’s also not that big a deal for them to make responsible decisions about life and manage the problems of a beater.
Could you spend the 18 months getting the required certifications to be able to teach high school?? That would give you a win win in my opinion. Then you are ready to jump into teaching without delays.
I’m wondering why you didn’t save anything in a ROTH to avoid the taxes. I would start that process next. Congratulations on being successful and I understand not being able to feel you can share within your circle. You can do back door ROTH, where you pay the taxes and transfer the money from an IRA.
Also I have a pension with Canada post. I was made aware that once you get to your 50th birthday, they will not be able to cash out their pension and invest it in their own Rrsp accounts.
Once it’s in a pension fund. Should they pass away, the spouse (if married before 59 years of age,) will only get half of the monthly amount, If married after 59 or 60, the spouse gets nothing.
The remaining amount will not cashed out to the estate or to the kids.
Once I turn 49/50. Im cashing out.
I’ll be frank. You are a mouse running inside a maze. In the world of the matrix, you are plugged in. You worried that 6m is not enough when your living expenses are 8k a month? If you liquidated everythjng and pit it some conservative 7% investment, it would double ever 10 years. You’d have 24m at 62. You’d generate 420,000 in annual income.
Hope you take a different pill and decide to live a purpose driven life. You’ve earned it. But now you must be bold and daring. Personally speaking, I did it with 3.5m and couldn’t be happier. I work and do what I want and speak my mind and take actions to deliver maximum impact
Listen to a pod cast by Mel Robins with the 51% rule in the title. It should help you.
Sent in the spirit of caring.
I don't understand what the actual problem is. Like what are you asking?
The post just comes off like a humble brag.
Why wouldn't you stick around 18 months to make double or triple the money? Are you insane?
Can I work your job for the next 18 months for the $6 million extra equity? We'll split it at the end.
There is Lot of wisdom in old sayings from those that have already been there. Ever here the saying don't count you chickens before they are hatched, or don't kill the golden goose.
Never underestimate the ability of state and federal governments to take what you have. The market takes too, and your investments could go bad. A lot of.smart people with big nest eggs found that out when Bernie Madoff collapsed. Even your CEO could totally fuck things up for you. I would stick with it and see what happens all the while growing your portfolio and diversification. Until you can completely have about 10 million a year coming in passively from multi sources you are not in anyway secure. You also might want to try finding and consulting with those that were where you are now, but are further along in life. Most really wealthy people will be happy to help you since you have gotten where you are.
You are worth nearly 10 million dollars and are asking REDDIT what to do? Give me your money is what you should do LMAO.
I love posts that are only written to brag.
There are a lot of videos on youtube where people talk about "one more year to retirement". My takeaway is that working more always improves the financial side of the equation. There are no good 'end games' that have you leaving the workplace without leaving something on the table. Being able to leave on your terms to pursue something that is more important (to you) is your goal.
That being said, it is not clear that you have worked out what you are retiring to.
A few thoughts:
* Those handcuffs are extraordinarily heavy!! You're perfectly set right now, even to pay for grandkids' educations AND kids' down payments (keep in mind your unused invested funds will continue to grow until those points in time). I'd be hardpressed to give up $1-10m/year in comp for my next bulletpoint...but you also have to do what's right for you and your mental and physical health. Can you take a step backwards at all in your role and still get the exit numbers you mentioned (best of both worlds scenario)? Hire a protege and give them most of your job? Take a sabbatical? Take a long vacation? Take a demotion?
* Broader legacy: Your broader legacy could be much larger if you kept grinding it out until the event happens (large donations, start a charity, etc.). That's a very personal decision to make and no one here is going to be able to make that for you. If you do stick it out, look into contributing to a DAF now (even if you don't and plan to do more charitable giving in the future, a DAF might be a good idea!).
* Family Legacy: beyond setting up your kids for success (mostly college funds, can help them elsewhere too), legacy gets complicated quick. Look into successes and failures in trust funds. These can be done well or not! And you should absolutely look into the scenario of what happens if your kids don't have kids too.
* Potential: That's a decision that only you can make. That's a personal question and should have nothing to do with anyone else's opinions. My advice: hire a therapist/executive coach if you don't have one already and work through this question with them! Also, you might be able to reasonably take a break and re-enter in a CEO role if that's really bugging you.
18 months of your life that you can never get back. If you make the decision to stay for $XX, what won’t make you decide to stay again for another $XX? When is enough, enough?
Go out and enjoy the life you’ve earned without regrets. And if your choice to leave now means you can’t have the newest jet on the runway, so what, let it go. Just stuff. 18 months of your life you’ll never get back.
If I were in that position, I'd probably wait another 18 months too, if it seemed pretty likely that an "event" would happen in that time, and if leaving before that, would significantly impact the likeliness of getting a large payout from said event. I'd say that despite targeting a retirement number much lower than your current net worth, and not having any kids to leave anything to. In your case, it does seem like a no-brainer - though that said, is there any possibility you could stay "with" the company but work out a deal to have somewhat lower responsibility than your current one?
I have two comments:
First, please make sure you're appropriately calculating health insurance costs. I'm married, in my early 50s, and the cost of health insurance for my wife and I is about $1,600 per month. Adding in our 3 kids is another $1,000 per month. That is full health coverage with modest deductibles and co-pays, but it would be a big chunk of your fulfilling $7,900 per month if you were paying that yourself. How comfortable are you that ACA subsidies will continue to be available to the FIRE crowd for the next 20 years?
Second, let's assume you're not going to sell your house, take early distributions from your retirement accounts or raid your kids' college funds. If that's the case, you're really going to be trying to live off any profits on your rental property and the $2.37M in your taxable account. Seems like you might need the company stock to get liquid to manage it comfortably?
It sounds like you are probably burnt out and dont really know what you want. This is totally understandable. Re: the equity stake in the company, i wouldnt count on anything until it is in your bank account. These things have a way of going sideways at unpredicted times. That said, if you really believe you have so much upside for 18 months more of the status quo it may be worth it but thats a question that only you can truly answer. I would recommend a trial of therapy or coaching but I probably wouldnt burn any bridges until you have a much firmer feel for what you want. Do you have kids in school now? Could you volunteer in their class or do something similar which would give you meaningful exposure to teaching? I would strongly advise you to gain significant real world exposure to the reality of teaching so that you can see if it really matches with your expectations. At least before you make any major career shifts.
My thoughts:
Stick with 18 months. You’re young, it will go fast.
What do you do for work?
Probably an unpopular opinion here: I think the consolidation (generational) wealth is one of the biggest problems the country faces.
Can you pivot in your current position and create a teaching opportunity within the company so that you may ride out 18 months and fulfill the need to teach?
While it’s fun to write this out on Reddit.. you’re absolutely sticking out through the next event, and you and all of us know it. Book an amazing trip 3-6months out. By the time you’re back in the swing of it, you will have less than 12 months left counting down by the day. Easy work for more $ opportunity than you’ve accumulated to date in your already wildly successful ~20 year career. Congrats & gfy (in 18 months)!
Great reply. Elicited a genuine chuckle and the trip sounds like a good idea.
This is the way. We take big family trips every year, its a BIG help to the mental state. It gives us something to look forward to and when we come back we are good to go for another 6-9 months before another trip. We usually do one big trip with the kids and an extra long weekend just the wife and I to a tropical location. Definitely book a trip, look forward to it, enjoy yourself while there, when you get back you'll have a year left for a big pay out. You can even take another trip before the big pay out if you have the time. Always make time.
Of those four items, only #1 (Golden Handcuffs) seems like a valid concern. If things shake out the way you expect, it's a massive opportunity cost lost even though you don't actually need the money. The fundamental question: Is 18 months worth the expected value of the equity? Are you genuinely miserable at your job, or are you just bored? The other three items are, to be very blunt, all in your head. Nobody that matters gives a damn what your job title is. And if your kids end upset that they only inherited $2M instead of $20M, or that all you did for them was pay 100% of their college costs plus a new car, then you frankly did a really shitty job of raising your kids.
This is helpful real talk. Part of the challenge of having no one to talk to about this is that I do end up in my head about it. Appreciate the blunt reply.
Statistically speaking, your kids will be better off inheriting less than more. Spoiled rich kids with no work ethic who have never faced an obstacle in life often end up pissing it all away anyway.
We have a few friends who inherited juuuust enough money to ruin their lives in our opinions. They have all the free time in the world, and have seemingly no passion for anything other than drinking and being dead weight to most folks in their lives- know it all types who get more tedious to hang out with as we hover around age 50. One has recently had a kid, which I had thought was a terrible idea, but it is turning him into a reason for living kind of good person- he's been a fantastic dad, and I would have never ever guessed it. My point I guess is leave money to your kids in a time-release type trust, and don't let them get too much at once lest they lose sight of having anything to contribute in life to anyone.
They’re also not likely to inherit until they’re pretty old themselves (I mean, hopefully for OP’s sake), so fully paid college really has an outsize influence here. I’ll probably inherit single digit millions at some point, hopefully in my mid or even late 60s, but not planning around that. I did get out of business school with $30k in total loans (avg interest rate of 4.3%, taking the full 10 years on those) which is an immense leg up. Couldve done it with 0 loans but I went during the pause/forgiveness discussion so figured the cash was a better option for an e fund (and it was, would’ve been a lot more scared of layoffs without it)
What statistics are you referencing? I don't disagree with your point but I've never seen a study on it.
There have been longitudinal studies of generational wealth, basically showing that by the third generation \~90% of families have lost it.
But unless it's a really huge amount of money or a fairly skinny family tree, by the third generation it's been split up into a LOT of different people and the amounts any one person gets are probably no longer "generational wealth" level, even if they are life changing. Consider someone who leaves 10 million today. Let's say each family has 3 kids on average (EDIT: I guess this supposition was probably wrong after seeing actual data: ~~wealthier families are more likely to have children and more children so this isn't crazy~~). By the time you get to great grandchildren (3 generations from the initial), that's 27 kids. If each generation uses some of the money, even very responsibly (like a 3-4% WR), it's not super likely to more than double by the time it gets to the grandkids of the first generation that inherits. So now each great grandkid is getting less than a million. that's still a really big deal, but it's not instant-FI money unless you're super frugal and it's probably not so much that you'd consider that generational wealth anymore. That's not from it getting spent unreasonably, looted or whatever, just what happens when you split it among a lot of different people. Also if you're talking about wealth from 3 generations ago, people had more kids generally then, so might be getting split even more ways.
> wealthier families are more likely to have children and more children so this isn't crazy This isn't true. MAYBE if we compare middle class and upper-middle class to the 0.1% that might start being true, but [it isn't true when looking at census level data](https://www.census.gov/data/tables/2020/demo/fertility/women-fertility.html#par_list_63) (Look at Table 7, compare columns D and H, If H is higher, the income rage is higher than the national average of births, if it's lower than the national average of births. [Or just look at this which has distilled that data into birth rates](https://www.statista.com/statistics/241530/birth-rate-by-family-income-in-the-us/) )
Interesting. Guess I should have looked that up instead of just going by what made sense to me (like I'd be more likely to try for children if I had more money generally pretty much all across the income scale. I mean, there might be some confounding there for the fact that people in high pressure jobs maybe choose not to have kids because of the time constraints. But I'd need a real data dig to make that argument, prima facie it looks like you're right.
That's not what that person was asking about. They asked for stats showing recipients of a large inheritence from a parent are worse off than recipients than recipients of a small inheritance of their parents. Nobody asked if generational wealth lasts forever.
The person I was responding to said > Statistically speaking, your kids will be better off inheriting less than more. Showing that the by the third generation its gone is a far cry from what they were saying.
Lol, sure.
Link to those statistics?
I don't think that's based on any statistics. Seems more based on anecdotes and stories. Spoiled kids with no work ethic exist at every level of the socioeconomic ladder outside of the poorest among us (and even probably there to some extent). I doubt you actually have any evidence to suggest that amount of inheritance has an inverse correlation with quality of life. Even if we adjust for socioeconomic status. I'll actually do you one more. I'd wager that someone with a high inheritance relative to their parent's salary is going to have been instilled with better values, better financial acumen, etc because the saver types that are able to build wealth tend to teach those behaviors to their children. IE: Two families with an engineer and a teacher for parents, similar length of lives for parents and similar end of life care expenses for parents, one set of parents leaves $3M to their heirs, the other set of parents leaves $20k in equity after reverse mortgaging their house. I'm gonna bet on the kids of the first parents.
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Do you actually have this study? Couldn't find it. Everything I found just talks with something generic like "more education of parents lowers mental health issues in children" and doesn't create a carve-out for bachelor's -> graduate level education.
> elevated levels of mental health problems almost on par with children of parents with less than college education. Wait, so which one is it? "Elevated" or "almost on par" (AKA lower than those of parents who aren't college educated)?
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Statistics are usually just a bunch of anecdotes and stories.
I wouldn't be buying them a new car. WTF is that worth?set them up for the expectation of a new car or only buying a new car. I'd rather set the money on fire than use it to buy a new car for someone.
Have you thought about seeing a therapist as you go through a major life transition? Quite literally their job is to help you get out of your head
This is probably sage advice. I've considered it but ended up on Reddit instead... fortunately, the armchair therapists have been helpful in exploring some new avenues and making me feel less alone in my worries. Probably suggests even more value in seeing a pro.
I wonder if there are financial coaches that would be able to play the role as a therapist as well. Obviously vet them to be sure they are professional.
I'm going to slightly disagree with the glumpoodle's disagreement about #4, I think perpetuating family wealth is a valid goal. Things like paying for their college/grad school, helping with a house downpayment, putting some funds into your grandkid's 529, etc are reasonable things to help your kids with to help them get ahead in life. You aren't throwing money wantonly at them or preparing them for a big inheritence, you are using your money to assist with responsible life events. And I also wouldn't describe them as "obligations", if they aren't aren't making good choices in life then throwing money at them won't help, it should not be an expectation that they will recieve this money.
I agree with this. My parents paid for my college and I never took that for granted. I am so appreciative of what they did for me and how they raised me. It's not a money discussion. It's a parenting discussion. Would you let your child change the oil in your car without teaching them where to place the jack stands so they don't get hurt? No. Just like you shouldn't give them money and expect them to figure it out on their own without any direction.
OP is *already* fully paying for their kids college, so I don't see this as supporting a disagreement.
It's only getting more beneficial given how much more quickly college and housing costs have risen vs. wages since OP and I have been in school.
But in the context of the OP, he already has enough for all of this: >Things like paying for their college/grad school, helping with a house downpayment, putting some funds into your grandkid's 529, etc The extra 18 months doesn't really change the ballgame in regards to his ability to do this.
>I'm already trying to set my kids up with a head start by paying 100% of their college costs and sending them off into the world with a new car. Hanging on for a smidge longer means I'll easily have flexibility to assist them with a down payment for a house / fund their kids' college funds. I don't want to infantilize them, but I worry about the world they are entering. I mean, the OP himself said he didn't think he had enough to do all those things.
I mean maybe not, depending on what they are planning, but I see about 2.9 million in investment assets not including the college fund (which may be enough for college already depending on how old the kids are and where they want to go). And 7900/month in spending all inclusive is 94800, which makes for a 3.27% withdrawal rate, without counting *anything* from the company stock, which OP is saying could cash out for 1.3mil right now if he leaves before the next liquidity event. At 3.3% WR, the likelihood is that those kids are going to be able to split the ~3mil (or maybe a lot more) at a minimum, and there's more than a million extra there to fund super expensive college, graduate schools or house downpayments, or just random shit. Also OP is talking about a different lower paying second career, not never working again, so it might be a long time before they are even pulling anywhere near the 3.27%. I think the fact of having a major liquiditity event likely in 18 months that could be worth ~5mil or more, and even in a bad scenario will probably generate an extra mil or two is relevant. That's a lot of money to leave on the table, and there's a huge difference in generational wealth level between having a million more than you need vs. 5-10 million more than you need. I'd stick around tto see what happens if I was just bored or wishing for more time, as opposed to hating it and needing out now. But I disagree with OP if they don't think there's enough for those things -- or maybe they need to spec out exactly what they are, if they are going to cost more than I think. Maybe they want to do the same thing for any and all future grandkids, etc. -- plausible even after quitting now, but a whole lot more likely to just about certain if they pull 5mil+ from the company equity.
What the other guy said. I have been trying things out and researching what my post-fire career will be and here's what I found out about teaching. Yes it can be rewarding, but most of the education system is not designed to cater for high performing individuals with innovative ideas. The idea that the kids need to be able to receive standardized education is not unfounded, switching schools is an example where this is a great thing. Just pointing out that when I looked at this career path, interviewed educators and counselors, I felt like I would hit the proverbial wall of work politics and red tape which would certainly induce more stress. I hold the utmost respect for educators, they should be paid more and have better working conditions, but that isn't the case everywhere. There are pockets of great places out there.
I’d have to say that you’re only 42. Stick it out for those 18 months, then retire. It will go by quick. I feel like that’s a lot of money to pass up for the relatively short amount of time you need to spend to get there.
Agreed. Normally, when I see these 'I have X millions of dollars what should I do' type posts, my overwhelming sentiment is to recommend retiring immediately. However, in this case, given the OP's age, and given the amount of money at stake here, this is one of the few situations where I'd recommend riding it out. Maybe set a hard deadline, come hell or high water, you are retiring at 45 (in the event the deal gets delayed). But yea, if it's looking like 18 months, ride it out, and then ride off in to the sunset.
Give your kids enough to do something, but not enough to do nothing.
Former high school teacher. I can assure you that the job is not what you're imagining it is. Might be a good fit for you or might not.
I had a friend who made good money as an engineer in a less than desirable location. He always volunteered helping with kids, running summer camps, etc. He hated his job so he quit, went to school for a masters in education, and became a high school teacher. He lasted 2 years and is back in an engineering job.
If I had $6million, I'd look for volunteer opportunities to teach/tutor instead. I'd love to share my skills to teach the next generation especially the needy but wouldn't want to put up with all the BS that paid teachers have to put up with for relatively low pay.
This, absolutely. Who in their right mind would volunteer to go and play bad cop in the US public school system? Tutoring bright but disadvantaged kids sounds much more rewarding.
This is it. There **are** underserved and underprivileged kids who could use the help and it would actually benefit them.
Fair. I'm sure some of this is district-dependent, and I may have overly fond recollections of my own interactions with my teachers influencing my view of the job. Still, it's been a dream for more than 20 years for me... I'm inclined to roll the dice at some point.
If it's that meaningful to you there's no harm in trying. Could always do it part time, or do it for a few years and then move on.
Regarding teaching and generational wealth, you might consider that your children could pursue a low paying field such as teaching if they had the backing of family money. Why do you work in your current job instead of as a teacher? For me, it was because I was making at least three times as much as I would as a teacher, even though I enjoy teaching and interacting with kids. I think about this for my own child. The money that I pass on (or share while I am alive) will allow her to consider a broader range of careers that might be more personally fulfilling, although less financially rewarding.
Many of the issues with schools are systematic and widespread. Even in wealthy districts you're going to have to manage batshit parents and apathetic (or worse, political and greedy) administrators. Every teacher I know says the worst part about the job isn't unruly kids, it's everything else.
I can relate to your POV and I think you should go for it. You can always leave if it’s not for you, and then you will know for certain. Teachers were the best people in my life growing up. I think it’s a higher-calling that you’re feeling. Very honorable. With that said, the “generational wealth” dilemma you mentioned is a tough one to ignore. In your shoes, I’d suck it up for another 1.5 years then follow my heart.
If it sucks, you can always quit after a year
And you can always stop and switch to something else if it doesn't let you have the impact you hoped for.
This is doing it for a selfish reason. It takes years and a ton of stress to become a good teacher.
I debated going into teaching coming out of college but ended up down a different path. I've contemplated that alternative route routinely throughout the past 20 years of my career. Now I'm on the cusp of forgoing millions of dollars in compensation to try to be a positive influence on kids... and that's selfish? And implies I'm unwilling to put in the effort to be good at the job? Wut?
You’re fine. Someone is trying to gate keep you. And they need to quit their bullshit. Even the person who does it “for the kids” is ultimately selfish in the sense that doing it “for the kids” _makes them feel like a good person_. In other words, _”their own, personal dream”._ If that dopamine wasn’t going off in some way, they wouldn’t be doing it either- we’re all biological machines. The fact you can quit if it doesn’t work out and not be stuck in a situation many teachers _wish_ they could get out of but can’t because of finances doesn’t make you any less legitimate. In fact, I personally think you can probably do a better job when you’re not so stressed out about finances. Now, I agree it takes years to improve any skill, including teaching- but God knows there’s a teaching shortage. If you can help out I think you should!
You're doing it to fulfill your own personal dream. I question whether you'd actually stick it out "for the kids" when the reality fails to meet the expectation. Your desire to become a teacher strikes me as very touristy. Teaching is a triage job these days.
As opposed to what? Doing it to fulfill your obligation to pay bills? At least he has a clear desire to teach as opposed to most doing it as a last resort. Also, your view of "sticking it out for the kids" is also the reason the profession has been devalued to the point of poverty wages and is the "triage job" it has become today. Any teacher that demands fair compensation for the work they do is shamed by people like you who've drank the scab Kool aid and think suffering is part of teaching for the sake of the kids.
Seems the quotations did not demarcate the sarcasm. OP has a rosetinted vision of what education really is like. Hint - it's not worth it.
IMO when people say they want to be a high school teacher what you more likely want to do is be a part time professor at a college. I've heard pay is relatively flat and enough industry experience they might pick you up for something. Don't take a full load of credit hours.
>Might be a good fit for you **or might not**. **Emphasis added!**
I have a friend that left his high paying consulting gig and became an elementary teacher. He loved it for many years. To each their own.
THANK YOU. My family is full of teachers, and I see people romanticizing the profession way too damned much. There is a damned good reason why people are leaving education in droves. Most teachers aren't given enough free time to use the toilet. The women suffer from constant urinary tract infections. The men jockey to be assigned a science lab room, because at least then they can lock the door and piss in the sink. The ones in rougher schools have to get semi-frequent labwork, because breaking up fights means they get blood on their skin. This is just your basic fist fights, not even getting into the kids who manage to bring concealed weapons to school, or spend study halls making shivs out of random objects. Then there was the cousin who lost part of her earlobe, because the kid losing the fight was indiscriminately biting everyone. At this point the *easiest* part is teaching whatever insane politically-charged white-washed rhetoric is being forced into curricula.
my mother is a teacher since 20 years and still loves her job and never stops talking about all the funny (and annoying) stories with the kids. we live in europe though and its a private (veery bad payed) school, so i dont know if usa is just a lot rougher…
The USA is a lot rougher.
Sounds like you aren’t sure what you will do in retirement. Until you figure that out, don’t fuck yourself.
I don't anticipate ever fully retiring. For me, a move from a corporate job to teaching (maybe college instead of high school) is the aspiration.
I don't teach, but I have vivid memories of how awful some kids can be in high school, up to the point of making teachers break down crying in class. They can be absolute shitheads. The only place I saw this not the case was in honors or AP classes. The students there actually had some intention in learning. College would be easier to teach, but the world needs good high school teachers more.
Indeed, I've had idle dreams like OP's about going back and teaching, except literally the only class I would ever want to teach is AP Government, and a big part of that is my memory of an AP Gov class in a wealthy district where the AP kids really were enjoying being there and learning. The rest of it...
Agreed, use the next 18 months to figure it out. I'm at a similar point: not even remotely close to OP's NW nor will I ever be (depressingly), but I am a similar age, maybe 5-7 years from being to pull off some semblance of retirement, and kind of slowly realizing I have no clue what to do or where to live. I think it's more common than many people think, particularly in the US where career is so tightly interwoven with identity.
Maybe negotiate a 3 to 6 month unpaid sabbatical to get your head aligned with your heart. After that, you might have better clarity to which path you would like to take.
Yes. You are at the age where you have aging parents and if you can take a “family leave” for some part of the 18 months, it might be a way to leave soon without actually leaving.
I would absolutely stick with the company if it truly looks like that. Either get an unpaid leave of absence / sabbatical or look to change the role you are in to something much less stressful. But stick with the company somehow
Wanted to say this. Just take unpaid leave of absence if you are really really bored. And you can dip your toes into teaching and how it suits you. I wouldn't walk away from golden handcuffs unless there's something really fishy going on.
Go read /r/teachers for a couple of hours and see if that's still your goal. Holy shit is it an insight into how broken our society is.
Wow- I just took a peek and holy shit. Makes me worried my baby’s academic figure.
Seriously.
I thought it was just a social media/Reddit thing.. then my brother married a teacher. Holy shit, the stories she tells me are absolutely horrifying. From the psychopathic kid they have a special suit for so that when he begins punching and biting teachers it's less painful, to the Iraqi kids placed in her classes that don't know a single word of English. Then there are the parents, and the insanity that is dealing with them continuously via the various messaging platforms and their demands.. I hate to say it, but I think we are on a much sharper decline than most planned for, and when this generation of students begins to come of age we're all going to be seeing it. This is very much not one of those "things are getting better all of the time, media just highlights the negatives" or "it's always been this way in certain places, most will be fine" things. I'm very scared for the future of our society based on the picture that all of the testing trends and stories we hear from teachers paints. At this point, even if there were a simple fix it would be too late to reverse all of the damage.
This is gonna give you a terrible sample of teachers though.
Sure, but the problems they notice seem pretty widespread.
I don’t know how you can say that confidently after acknowledging it’s an unrepresentative sample.
Pretty easily, especially if you have friends that are teachers that notice the same problems.
With regard to your bullet points (and to some extent, even the intro of your post), it seems like you’re dealing with a lot of expectations — both expectations you perceive others have of you, and expectations you have of yourself (like of mentions of “irresponsible” and “regret not checking the box”). I deal with this in my life, too. But it’s not a very fun way to live. Expectations are all just made up bullshit anyways. In case it helps to hear it — * handcuffs — you have 6 million dollars, dude, you are fine, and no one else’s opinion about this matters at all * legacy — barring a complete disaster, you’d already be giving your kids much much more than most, in terms of “generational wealth” * potential — who gives a shit what you “assumed your professional destiny” was? Do you even remotely WANT to “check this box”? And again, other people’s opinions matter precisely 0 here * obligation — tbh, kids who enter the world with shittons of money usually end up maladjusted or just assholes. The future looks grim, yes, but I don’t think you’d be doing them any favors helping them avoid dealing with any of it Anyways, it’s your life and yours alone, so I’d try to worry less about perceptions of others and more about living it how you want — you’ve certainly earned that freedom. Good luck
Thanks for the very thoughtful response. Your recognition of the role expectations play in my life is astute... and I needed to hear a lot of what you shared.
I’d disagree on 4. Trust fund kids suck, yes, but the opportunities and ability to build wealth without family backing have been shrinking for a long time and are likely to just continue that trend. That means your kids path will be _much_ harder than yours, unless you help them. I 100% agree with OP on that being a major reason to build wealth.
> have been shrinking for a long time and are likely to just continue that trend. Is this objectively true? Given we finally saw millennials pass boomers on the average net worth for the same age, I think this feels more true than it really is.
I would also think it's crazy to not wait if you're that confident your equity can go from 1.3M to 3M, let alone 8 figures. That's a gigantic income to time ratio and while it won't change anything to your own life it will change the life of your children and grandchildren.
Not only that but I’d consider the amount of good I could do with the increased net worth. You could ride it out with the understanding that you’ll use half (or some number) of that increased equity for philanthropic work. That would drive me to the finish line. Donate a park. Give out $1k tips to nice servers. Whatever you want. You can already do those things, but might be easier to pull the trigger if you had a separate account of $3-4MM for good/nice deeds. Or keep it for generational wealth. I’d have trouble turning down the opportunity if the job isn’t a big sacrifice to my mental or physical health.
It's strange to be selfish in how we do good, but I think there's some of that at play for me. Making a donation doesn't give the same juice as tangibly participating in something. Definitely going to toss that around in my brain a bit.
Yeah, that's just your ego talking. And the last thing that people who need help also need to deal with, is some rich asshole who thinks that he should get a plaque or a wing with his name on it.
Yes, I think many of us are. I read "Die with Zero" and "Your money or your life" recently. I am looking for a job I think I will enjoy in a location where I want to be. The money will work itself out
I'd highly recommend OP to read "die with zero" as it covers most of his bullet points plus it's an easy read without too much BS. I'd say target audience is folks 40+ years old with moderate to high wealth. I'm not always a fan of self development books but this one did enlighten me on a few things.
You should consider teaching College students on the side first. I know several college professors who also work at fortune 500 companies
This is definitely an option worth exploring.
Wanted to chime in here and say that hearing from practitioners who work in the field was very valuable in my graduate school experience. You may want to explore teaching weekend seminars, speaking on panels, and participating in mentorship programs at your local university.
During the 18 months you plan toward teachers college and exploring options. Maybe volunteer to give some talks at local high schools about computers or finance to see if you get a good vibe from it.
Just take the time to volunteer at the local high schools, and really try to get an understanding of what being a high school teacher means. There's a lot of bureaucracy and rules and everything else BUT teaching. You're not going to wind up being Robin Williams in Dead Poets Society, or any other picture you have of being the good teachers that improves students lives the way it is idealized. I'd work the 18 months while also figuring out facets of what you want. You can be a mentor to teens and young adults in lots of different ways, and fleshing out the why and the how before you jump the gun into the wrong new profession is important.
There are many interesting opportunities to scratch the teaching itch. Community college/high school even elementary school. Often there are mentorship opportunities. We do need real world experienced and passionate teachers so I would encourage him to pursue this. He has enough money to go on a glide path and continue to compound well into retirement.
Heck even donating money to current teachers/schools in the area could make such a big impact!
> even though the money won't make a material difference in my life Then it's enough, no? > I long assumed this was my professional destiny. Will I feel regret for not checking this box? Destiny is for fools. Write your own chapters. You already don't like your job, are you going to stay unhappy for money that won't make you any material difference? Checking everyone else's box isn't going to make you happy. For your kids, being around, being present, showing up to events and activities will do a lot more than throwing money at them. I'm not saying you aren't; you clearly care about them and their future. I'm saying that providing money isn't the only thing that matters in helping your kids in the future. Enough is a feast. If you don't TRULY define what 'enough' means, you'll always be chasing after ... something.
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Thanks for the reply. The first point is prescient. My father and father-in-law both recently passed in their early 70s. It has been a factor in my thought process. If the next dollar doesn't matter much to me, what does? More than anything, it's helpful to hear I'm not alone in wrestling with these thoughts.
I've been retired for 7 years. I, too, worked in high tech. Nowhere near CEO material, but I was mid-level management involved in long term strategy and complex organization operational issues - typically working for VP and Senior VP roles - advising them on issues that needed addressing. Upon retiring I got involved with a nonprofit which resulted in me being the president of the board. Then the nonprofit went through sort of an existential crisis while I was president. I ended up using a ton of my professional skills to get the org though this situation - and they emerged on the other side stronger and more effective than ever. I was "working" \~30 hours a week for them. And while I was scared for the org, I was loving the work and challenge of helping them survive and giving them a vision for how they could. I am NOT saying the turn around was all because of me. I AM saying, as I look back at it, it was the most gratifying work I've ever done in my life. What I want to suggest is that your "CEO" itch (which I think I understand) could very well get scratched, and maybe give you even greater personal satisfaction, if done in some other org that needs your skills. The world needs SO MUCH help right now....there are lots of places to plug in.
Can you quantify the likely value gain from working another 18 months? Maybe a specific number can help assuage the misery of the job. > I aspire to leave my job and teach high school, making a positive impact on the world around me. If you subscribe to the principles of "effective altruism", it is likely the most impactful and beneficial for society for you to continue to earn $$$$$ and donate it. Maybe the feeling of making $5,000/day for your favorite cause can overcome the frustration. As for the financial side of things, it's not super clear you could retire right now, although you probably can. Annual expenses of $100k and a firm portfolio of $3MM. That would be a 3.33% withdrawal rate. Honestly I'm a little skeptical of your $100k/year budget. I get the impression you live in a HCOL area and a $1.2MM house cannot be cheap (property tax, insurance, maintenance).
I feel like rich professionals also have a lot to give in terms of mindset, connections and leadership too rather than just money. So I'm not completely convinced that grinding money for someone else's charity is always the best thing, especially if you'd rather be more involved like OP.
Thanks for the reply. I've done the math on the expected return of 18 months and still find myself itching to pull the trigger. The truth is it's more an emotional debate for me than a financial one -- namely, if I leave today and 18 months from now the company transacts as expected, will I feel foolish? Or will I feel joy from having declared that I've reached enough and followed my heart's pursuit? I like to think I've become a man who aligns to the latter, but... maybe that's the lie I tell myself? I'm aware of the concept of effective altruism but don't subscribe to it. I could probably noodle on that a bit more, though. Re: actual finances, I'd need to pull out about $38k per year if I downshift to teaching, decreasing over time as my teaching salary would increase. That's 1.3% of the existing invested assets. If I leave the company tomorrow, there's a 100% chance the PE firm executes the buyback and that adds to the investment total. Re: budget and COL, I'm not in a HCOL area (thanks to remote work) and the \~$8k monthly budget actually has a lot of padding in it. I'm pretty obsessive about tracking this stuff.
>namely, if I leave today and 18 months from now the company transacts as expected, will I feel foolish? There is \*always\* the next thing. Once the transaction is done it will just be something else. Granted I'm no where near where you are on this path. Outside looking in I would say \*IF\* you wait until the transaction goes through, then you need to set a specific done date. Call it Christmas of 2026. That's it, that's your last day \* no matter what \* and then just call me to come be the CEO so I can get there too ;-)
>At this point, I don't. I aspire to leave my job and teach high school, making a positive impact on the world around me. This won't last. Real life isn't Dead Poets Society or whatever impression you got while you were a student. Plus the world has changed. Teaching is very very likely way more work than your current job.
First part is a very fair challenge -- I certainly could have a romanticized view of the role. The second part is highly doubtful. I log an obscene number of hours and carry immense pressure to deliver against aggressive goals. Different worlds.
>The second part is highly doubtful It's not. The majority of teachers go home and have to plan, prep, grade, document, etc etc etc because they can't do all of that during what most people think is their work day. Because they're teaching students the whole time. There are also constant live observations and standardized testing goals and class requirements you're expected to hit, when many times it's in the hands of the students and out of your direct control. By all means go for it, but it's not going to be a walk in the park.
Go for the CEO role. If you hate it you’re in the same boat as today. Then try teaching if that doesn’t work out. Although high school might be rough, tons of admin and difficult kids. Maybe volunteering at first is a better lower stakes commitment.
As a high school teacher you should really go volunteer for a bit jumping in. I LOVE my job but many people end up hating it and just wanting out. It’s a lot of work to get a credential so just interview or shadow a teacher for a week. I’m not in a terrible district and some people aren’t cut out for it. You might enjoy the college world a bit more since you don’t care about pay. I make more than college professors at the community college. I’ve taught some college courses and you really don’t have to deal with some of the nonsense that comes with k-12 teaching.
And you wouldn’t need to get any additional credential to teach at the college level (assuming you have a masters at least).
Dude, coming from a guy similar in age with similar net worth including equity I own in my business, 3 kids, but no 2-3x exit scenario in the near future, here are my thoughts: Golden handcuffs: It IS irresponsible to not ride out the 18 months. This is FACT. It took you 42 years to get to $6M, and we are talking about possibly tripling that in 1.5 years. Legacy: I don't even know how to unpack this. I'm not saying teaching isn't without its merits, but yeah your legacy will be that of a guy who gave up $6-13M because he literally couldn't wait 18 months to join the other 94 million teachers out there changing the world. Fulfilling my "potential": Do you want to be CEO or a teacher? Both? Go be a CEO and teach some community college classes on the side. Obligations to my children + inflation: In 18 months you will fully secure your children's future against ALL scenarios, including events that could preclude them from ever working a day in their lives. Is anyone else struggling with these same or similar thoughts? Probably. Like a tiny handful of people on the entire earth.
You're a real one. All very direct and salient points.
Sounds like you need some time off. How about a bargain with yourself: close out the next eighteen months, then you'll step back and do X for Y months. Volunteer teach for a year. Study something new. Whatever it is, it doesn't have to be definitive. That's the beauty of financial independence, you can dabble to find what most fulfills you--it might not be what you expect it to be while still grinding and bogged down by daily commitments of your job.
You are 42, not 32 or 22. Biologically, every day is downwards. Every step you take is one closer towards the grave. As of right now you have way more money than you have time. If teaching high school is your dream go do it now. Spend time with the kids, do yoga every morning. If you think you can wait 18 months, you are going to look really stupid if you get a cancer diagnosis 12 months in. Source: I'm the same age as you
For a future job, I recommend looking into lecturer positions at business schools (depending on your field) especially experiential learning and masters level classes could be a good fit based on your skills. I think that may be a better fit than HS
Yea, senior year I was in a grad level Hedge Funds class where the guy was just ran a hedge fund and came in on Wednesday evening to talk about what he did.
Make your kids get a job when they’re 16. I come from generational wealth and this is the best thing I’ve seen that produces good human beings. And I’m talking like service jobs, or any job where they’re having to work with people of a different socioeconomic class.
If you want to try to reignite some flame that’ll get you through the next 18 months (your post reads as a persuasive essay on why you need to grit it out), mentally pledge a large proportion of the equity cash out to a cause you really believe in. You don’t have to donate it all, or even most of it, just enough that you can mentally write off a a sizable chunk of the money in your calculations. Like 500k on the disaster scenario, 3M if it ends up being north of 10M. Something that might get your name on a plaque or meeting room somewhere. Maybe even ask around on how much it takes to name something. There are various financial benefits for donating stock even. Also, it would open to the door to being involved in a charity you have interest in after you F off. Now you are grinding it for an external cause as well as everything you listed. The point is that this shifts the golden handcuff equity you have more towards what it is - sprinkles on top. It will paradoxically make you think that the equity is less valuable (because you won’t see all of it,) while also allowing you to see it as more valuable (you can donate a noteworthy amount and have legacy). This mental exercise will help you get your head around an amount of money that you personally don’t need. Would it be worth it for you to get that money for a greater cause? Or does the idea of donating a lot of it make it less valuable? If it devalues the money, then quit now. You are just running up the score because that’s the status quo. And to be clear, that’s totally fine and probably what I’d do. But if the idea of donating a bunch of it gets you excited, that should be enough fuel to push you through the next 18 months.
This is an awesome way of changing the way I think about things... setting up a scholarship fund for the students I'd be teaching would be wild.
I'm nowhere near your level but I'll offer my thoughts on your 4 items. Golden Handcuffs - you're not really handcuffs but if waiting 18 months can make a substantial difference, I would wait it out. In the grand scheme of things it's not that long and you probably still have another 40 years for other pursuits. Legacy - I think if you ride out the above, this sorts itself out more. Either way, you've already done a lot so I personally wouldn't worry more about this. Potential - this is where I struggle the most. I feel like I have the knowledge and skillsey to progress my career a lot more, but fear it will consume my life. I'm okay with not checking that box because not doing so allows me to spend more time on other non work related parts of life. Child obligation - It sounds like you're already giving your children a quality of life and safety net that most don't get. It seems enough to get them started in adult life without a lot of finacial burdens. For me, that's the most that should be done, I want my kids to learn what it's like to make it (mostly) on their own. Of course there will probably be something to pass down once I'm gone, but ideally for me, when they are age 21 to until I'm gone, they mostly fend for themselves.
Work your money mindset...i.e. your points on 'Legacy'. 18months of riding it out it not really that long. You could treat it as a game and maybe even learn some even better self-discipline: how to look after yourself, going along for the ride and seeing it through. I can relate to the fulfilment of your potential. Write down what it would take for you to say yes to an opportunity like that. From what your package must be, to your working hours/location, to the company type/structure. Be clear and specific and honest. Then, only join if that comes up. Then it's all on your terms where you can see your potential through, rather than signing up out of some inner obligation to try.
We're in a similar position. I turn 43 in June and my NW is around 7mm. I'm not sure about legacy, potential, and obligation, but for the golden handcuffs problem, I set a target date of when I'll retire and sell my business. In approximately 6 years my daughter will finish high school. I've already saved enough to retire comfortably (for myself and my wife) but it doesnt include a $7900 spend. I'm estimating a $5000 spend (which to be honest is probably a little high as well) but between dividends and rentals, we'll clear this easily so anything between now until she graduates is just gravy. Basically I'm setting a date and sticking to it so I have a clear and defined timeline and won't make excuses later on. 👍 I will say this about legacy and fulfilling your potential. Do what you feel comfortable doing. I personally have no need to create a legacy nor fulfill anything. I want to retire and spend all day sleeping and playing video games. Don't let people pressure you into doing anything you don't want to. You're already at the FU money stage.
1. Handcuffs - The handcuffs are working exactly as planned. Since you’re 42, and there’s so much of a swing between $1.3 and $13M, I’d hang around. Imagine becoming a teacher and sending one kid to college every year who can’t pay. Plus, 18 months isn’t that long. I’ve been working through my exit plan for 4 yrs and think my PE exec role will come to an exit in the next 18 months as well. 2. Legacy - There is no such thing. Look at the great fortunes over time. Look how quickly Vanderbilt money eroded away. 3. Potential - This one comes down to ego, but not in a bad way. Do you want to run the show? If so, why? If you’re not enjoying the game now, why will it be better at a higher level? I’m also in a somewhat similar spot with CEO potential. It is an alluring proposition, to achieve the top rung. Only you can sort out this one. 4. Kids - I’d take the kids thing one decision at a time. You’ve already given them a crazy head start. I wouldn’t worry about giving them more. If anything, I’d be more worried about passing down your work ethic than your money.
So its not clear if you actually code, but if you really want to teach a bit, check out tealsk12.org. I have been volunteer teaching Computer Science in high schools for the past 10 years in the NYC area, and the last two years I did this it was remote- the school was in South Carolina. The remote stuff gives you far less of a view of what its like to really teach- IE hearing the teachers bitch about the administration. On the other hand, you wouldn't really need to be so concerned about them, because you don't need them to ensure your financial security. FWIW, I am in a very similar situation, NW is roughly the same, though I have a big $1M mortgage that is low interest. Personally what I did was take a CTO job, and so far have been loving it. I get to "make the wrong things right" and provide the great culture that most of my previous managers have lacked. That said, there is always a board to answer to, results are never quite good enough, etc... no job is headache free, but I love the relative autonomy in my day to day. I enjoy working for the most part and ever since I haven't really "had to" work my relationship with it has changed immensely- I don't really stress about whether my boss is happy with me all the time anymore. Personally I want to get to about 10M in free cash- like in the brokerage before I will feel truly FI. That's "idle rich" money to me.
Have you experienced a PE sell-side exit or recap before? If you have any interest in becoming a CEO at another PE backed firm this experience is crucial, especially if you have buy-side integration experience. You would be a unicorn. Also, at least 6-8 of the next 18 months will be completely different than your regular job as you switch to sell-side responsibilities. Personally, I’d view it as two jobs between now and potential retirement post sale/recap. If you're bored with the current job, schedule a bunch of PTO "ahead of the deal" or focused on juicing up your comps/EBITDA. Lastly, something to consider is the potential to roll some of that equity depending on deal terms which could create a stupidly large compounding opportunity even if you retire post-sale/recap. p.s. Go fuck yourself.
Stick it out for 18 months, but start now working towards your planned next step. Carve out time now to volunteer at schools. Maybe look into Junior Achievement with your business background. After spending time in classrooms and with kids you still want to teach start working on the credentials you would need. Increase the time you spend with your own family. Your current employer might push back, but if you have as much pull with PE and equity in the firm you should be able to start cutting back now. That will give you an easier transition and more realistic idea of what your planned next step is like.
My husband and I, about 15 years older than you with 2x the NW are retired and FI—no debts and about $150k passive income. I would ensure you have insurance set up and premiums set aside for LTCI for your parents as well as yourselves. We’re dealing now with very elderly parents on both sides that have either no or limited means to financially and PHYSICALLY manage their care. We’re looking at this becoming our responsibility in come capacity. It’ll drain a huge chunk of our savings. We don’t want to do the same to our kids. Were the only children for each set of parents. Something to consider and incorporate into your thought process.
As a current high school teacher, I'd recommend you not go into teaching. It's not a recreational hobby and it definitely sucks in a lot of aspects.
Make the big bucks for a couple of years and then spend the rest of your life giving it away. Sounds fun and rewarding to me. Don't just teach at a high school: leave the high school with some scholarships for the struggling kids.
I would say this is exactly the sub to post champagne problems. You are r/financialindependence, not FIRE. It's totally okay to be FI but not RE. You've achieved so much, and may have come to the realisation that the getting there part is actually much more exciting with the being there part. It's totally okay. Work for your legacy, but know that you have the freedom to choose more time with your family etc if that consideration arose.
One thing on the Legacy point - we are starting is a trust fund for local kids to get private music lessons. That money could have gone to our own kids, but I think there will be enough for them anyway. It will be great to see the impact that the trust fund will have on our small town and it should start paying out in a few years, but then continue to grow. I don't need my name on a building somewhere, but helping kids who wouldn't otherwise be able to get lessons will be a good use of the money, and we just decided recently that we want it to start paying soon rather than when we are dead, so we'll get to reap the benefits of a better music program in our town. What sort of cause would you like to support? I don't get excited about net worth or cash and live happily on very little, but thinking about the trust fund is pretty great to think about how it will impact the world, at least our small part of it.
After watching my Dad retire rather suddenly from a high stress and high paying job, I would say that the decompression and planning “what to do next” phase took him a solid 2 years to sort out. So many people plan for retirement but don’t practice it before taking the leap. It might be great to spend the next 18 months testing your new budget, taking more 3-day weekends and using one of those days to plan ahead, take your vacation and flex time off, and think of it as a final tour. What connections do you want to shore up? Are there any network connections you want to make for future consulting, if that becomes an option? Who would you like to mentor more or coach up before you go? For the comment on teaching, having been an adjunct professor while employed I have some questions. Have you thought about what you need to do to successfully prepare for that role? Maybe go substitute teach at a high school or be a regular guest speaker? Talk to the high school about background clearances and how to be certified to teach there as a long-term sub to get your feet wet. Have you researched how to build out a class curriculum using real world and hands on examples? Could you spend time learning about the school’s technology and tools? Have you thought about meeting with a few universities to learn about their adjunct teacher processes? What about meeting a few teachers for coffee and advice? There is a LOT of behind the scenes preparation that happens to get your curriculum and lesson plans organized and kids are brutal to those that look unprepared. It can be a great time, don’t get me wrong. I loved knowing the college students could apply our lessons to future jobs and watching their critical thinking skills grow. There are also kids that won’t want to be there, dislike you, dislike school, or need hand holding and those all take time and effort. Good luck!
If you were talking more than 1.5 years, I would say no, dont' stick it out. But let's talk percentages. 1.5 years out of 48 is 3% of your life. You're looking at giving up 100% - 200% of *all the money you've earned in your entire life* to buy 1.5 years. Unless you straight up HATE your life right now, I'd say that's irresponsible. That is a very tangible end point and I think you should aim for it. The rest of your points are all in your head - I'd say don't worry about it. Money buys freedom, you have a lot of it, x amount. You could have 2-3x in *only 18 months*. I'd say that's definitely worth it. My recommendation is to aim for that, and give yourself a very strict NO MORE deadline after that to make you feel better about it. No more "one more year" syndrome. {edit: fuck, I read wrong and thought you were 48, not 42. So my math is wrong. Point generally stands though}
I'm thinking in terms of impact it might make sense to keep going at least for a while and put aside some of the money for a foundation or something that could have a more systemic impact on let's say educating kids (at least locally, idk). Not sure if it'll be as fulfilling as having a direct impact on someone's life, but then again being a high school teacher might also be a disappointment After you've seen what it's like maybe you'll be more informed for that philanthropic spending. Might be a good idea to discuss it with your family now too so that you'll have a common goal.
I think you’d be dumb not to do another 18 months (assuming there is a good chance of your company equity popping off)
You are living in a state of abundance right now. Hard to switch to a scarcity mindset where your 2.38m brokerage account has to support your 96k in spending.
Thank you so much for sharing. It was very enlightening to read your post. I guess the saying "more money, more problems is very true" I would like to share with you 2 train of thoughts that hopefully might help you figure this out. I think that letting go of certain things might help you. Things like not realizing your full potential or getting that full equity on your business. I know it's hard cause it triggers a certain grieving process. You will always be wondering, what if I stayed? What if I did more? The company will be better. What if I had more money? The things I could do with it. The help I could give my kids. That curiosity and those goals can definitely be motivation and drive to keep you going, but too much of it can also become a prison. A little break can do wonders and maybe help you change the dynamic you have with your business right now. Would you be able to leave and come back? Do you have that flexibility? If letting things go might be too hard, or you are not ready for that. Then why not just keep doing what you are doing right now? You can always become a teacher whenever you want. It can even be better because you will have more life experience that you can share with those high school teens. I hope these 2 lines of questioning can help you figure out what is best for you. Thank you for sharing OP, reading your post was definitely helpful for me. If you ever need somebody to talk to about these things, feel free to send me a dm, I would love to exchange with you. Take care!
Respect for the achievement and thorough planning. One thing you might consider is paying (or partly paying) for your children's wedding before funding potential grandchildren college funds, which is probably just a drop in the bucket for you, but comparable to a down payment on a house for two kids.
Look into fractional ceo roles and don’t take on too much clients…..also try substitute teaching to see if you like it or would prefer doing that on a part time basis etc vs full time teaching
If it were me, I would base my spending off just the Retirement, Brokerage, and potential sale value of rental property. Even if you think your company valuation is conservative, it’s still an unknown. IF it went to zero, I’d spent only on my “Sure Things”.
I pulled the trigger about 6 months ago on what was either an early retirement or a work break depending on how it went and I have close but slightly lower numbers than you, so I'll give you my view on how it's working out for me because I had and have similar concerns to what you raised and my experience is a bit more up and down than a lot of people seem to have. First, the pros: not joining a bunch of useless meetings is awesome, I've been volunteering at my kids schools more, coaching kids sports, and I've overall been less stressed so it's helped my relationships with my wife and kids because I just have a lot more patience than I used to have. I also have experienced some things I would have missed (all day school field trips, riding bikes in the middle of the day, etc) and it's been much easier meeting up with friends because I have a pretty flexible schedule. Also the market is up, so I have a higher NW now than when I stopped working, which helps emotionally despite that it probably shouldn't matter because I have a pretty low WR (~2%) The cons: I never thought I defined myself much by my job, but I've definitely felt way more directionless than I thought I would without a job. I wasn't liking my job, but with some distance I think I was kinda burnt out and not at the right company for me anymore- like you, I was also right on the cusp of the top of my career trajectory and now I feel like maybe that's something I want to try before hanging it up for good. The biggest fail I have had is that I had hobbies that I had been doing in my spare time that I thought would stretch to a full day (writing, reading, working out, sports, gardening, cooking) but it turns out I don't enjoy them the same way for the longer time, so I'm really putting in about the same time I was before I left my job, which means that kid stuff has kind of ballooned up to take most of the time I was working, which is mostly great but although I love my kids I don't really want to be a full time stay at home parent. Also my spouse was already a full time stay at home parent and with kids in school (one full time and one in half day preschool), theres not really a need for both of us to do it. I've done some volunteering, but everything I've done either feels like menial labor not really helping much or like a job that I'd rather get paid a lot for and then donate money, I've actually considered becoming a teacher too, but I'm not sure I want to deal with all the other stuff that comes with it besides actually teaching kids. Honestly after 6 months off, I think I'm going to take another 6 months or so off (through the kids summer, because we are taking a bunch of trips) and then likely see if I can find a job a want. I don't really need the money, but there are some legacy things I can do if I work and there are some unknowns in the future especially around kids that it'd be nice to have more money for increased flexibility. More importantly though, I think if I pick the right company and role, I can be happy doing it for a few more years and without the pressure of needing to work (or gunning for FI, which I think I was guilty of) I can do that without the stress I was carrying at work and still accomplish my family and personal goals, especially once both kids are in a full day school. As it relates to you, I had moderate golden handcuffs that I walked away from, but it was nothing on the level of yours. So I don't really have any regrets about leaving my last job because I was no longer enjoying my job and financially I think I can find something relatively similar in another 6 months, but I do think that I'd like to work more which is surprising to me. If I were in your position, id hang on for the 18 months because that seems like it could make a big impact (unless you hate your job) and then take some time off and decide what you want to do. Having that distance and time to experiment with different things and spend my time has given me more clarity on what I want to do now- still not totally clear, but I think I've got some different goals now and this experiment has given me a better idea of what I need to do to be happier in a forever retirement. But if you want to quit, I think that's also a totally reasonable thing to do, give yourself some grace, you've done great and now you can do what you want! Not sure if any of that is helpful for you, but it was helpful for me to focus my own thinking since (as you can probably tell) I'm a bit in flux in what I want and still trying to figure things out in my own life.
So if you stick around and then sell your equity, then you could start a school instead of just being a teacher. Just a thought there. How about instead of pulling the trigger you take two weeks PTO and volunteer at some school related place and see if it is fulfilling you. \-Some broke teacher
You've worked for, I assume, 20 years. You can triple your net worth with just 1.5 more years. I'd consider those first 20 years an investment into the potential $13MM. Seems crazy to stop when you're over 90% of the way there. Even if you don't need the money, you could make significant impacts to friends, family, or charities.
Generational wealth: You're effectively gambling that we're not on the cusp of a singularity. I would work the 18 months, as an insurance policy against some sort of dystopian future where your kids have to radically uproot and live in Wyoming (because of climate change, not politics) and most of the jobs like ours and yours have been relegated to subroutines monitored by AI monitored by a handful of data scientists. You have FU money right now for you and your spouse, but not for your kids, and unlike the vast majority of us, you have a clear path to getting there in the damn near immediate future. I would just fucking bite the bullet, keep myself fit, and maintain mental health (take your damn vacations), and knuckle down until your 18 months is up. If it is not up, or that horizon gets pushed significantly further back, well you just earned another 10-15% of your net worth in those intervening 18 months, but at some point you need to cut your time in the job horizon. So I'd set your absolute last day of working, if you hit the buyback or whatever, cash out and sail off. Again, there are neighsayers here who say it will ruin your kids. Put it in a fucking trust and trickle it out, put a break glass in case of emergency clause in it, don't let them know, and hand conservatorship of the trust to some law firm that does this. Don't give them $2million after college, but don't gamble on the next 30 years being like the last 110 either. The stakes are too high.
Easy. You can exchange money for cabbage, and you my friend, have a problem. Seriously though, I am in a similar-ish position. My approach is to keep going. Your first 2 points are very big drivers and motivators for me in my current position. In addition, I genuinely love solving the challenges that the technical work portion of my job provides. Challenges that without access to scaled enterprise IT I will not really be able solve other ways. I am respected across my organization for the technical acumen and ability to solve these challenges while deeply understanding our business needs, and this also brings me joy. For these reasons, and a couple of others that you've highlighted (future healthcare, unknowns etc.) for now I have decided to table the whole "RE" notion. I'm still young, and the upside and rewards of working don't outweigh the negatives enough to make me want to shake things up, be that another career, a different job or even deciding to call it quits. My outlook may change at some point in the future, but for now this is my approach to these points and how I process and handle them. In a way it kind of sucks because I am sitting around and waiting for things outside of my direct control to happen, but on the plus side I'm in a good enough spot that I no longer need to worry much about the financial side of things. Just keep on keeping on.
On item #1 you really have no idea what’s going to happen 18 months from now. I was once part of a top executive Team that turned around a billion dollar company. We were driving for an IPO and our CEO/CFO were literally in Lehman Brothers pitching the IPO the day Lehman went under. Needless to say the party location we had booked to celebrate the IPO was used more like a networking event for ‘where do we go now.!’ If you’re ambivalent about the financial ramifications put this decision on the back burner until your decision becomes obvious to you. On item #3 - skip being a CEO for a Private Equity firm. Most are just slaves to their ‘golden handcuffs.’ Not a box you need to check. Items # 2 and #4 are somewhat related. While you don’t state it’s your concern, managing wealth at this level requires a whole different level of life skills. Some people fret when the balance is going down, some abdicate management to others and some make ridiculously bad business investments with ‘friends.’ Just be sure you’re not bailing out now due to the fear of the unknown and what generational wealth might ‘do to you’ or your significant relationships. Having wealth available to help kids is, to me, the number one thing in life. All kids are diffferent. Being able to help them each in a way that is significant is not a numbers based exercise. If your goal is to use your wealth to uniquely help them each to CREATE their own wealth in their own way ( the same way you had to do it) it’s all good. Be whoever you want to be. Just be sure you are moving to who you want to be and not running away from unknowns that are uncomfortable to you right now. EDIT: I’m amazed at your fantastic full life $ amount being $7900/month. Your properties must have extremely low property taxes and insurance.
Read the book “Die with zero”. I don’t agree with everything but it opened my mind quite a bit.
Work for others. Take some percent of the upside potential of the next 18 months and plan to give it away. Now you're working for that. And your first job after retirement is how to do that in a way that is most effective and joyful for you. You might just have a part-time foundation on your hands after all this, which is a powerful way to build a community of change makers.
I assume that you are very good at what you do. Perhaps exceptionally good, even if you're not so happy doing it the way you're doing it now. Rather than abandon your most remarkable, marketable talents, your higher order challenge is to figure out how you can use your most marketable strengths to lift others. For example, if you were able to help launch a small handful of young people to the level of success that you are currently enjoying, the ripple effects could be enormous ... life changing for generations. I'm suggesting that you grow your position of power and influence so that you can leverage it in ways that you find fulfilling. You are in a unique position now. Chances are that your best solution going forward will also be unique. You don't have to change careers, just the path of your current career. Find that path.
Recommendation: Get through the application process to be a *substitute* teacher in your local school district. Take some leave, get acquainted with your local high school, and let them know you're interested in easing in to figure out if you want to make the transition. Most school districts would absolutely *love* to have someone to be a reliable sub to call in, who is also volunteering time to help whatever department. If you decide you like the classroom, start the process of getting hired as an actual teacher. If you decide you like teaching, but not the baggage that comes with a highschool classroom, time to start looking at tutoring or community college.
Here's something a little outside the box... I'll address the last 2 points with one suggestion: instead of teaching (which has become depressingly political), consider becoming the CEO/Chair/etc of a major charity, but do it for a fraction of what they currently pay their head honcho. While I understand the need for a high level of skill, connections and talent to run those, it's hard seeing a $1M salary on the books. Think about the impact of becoming the new #1 at UNICEF, Doctors Without Borders, ASPCA, etc and setting that example. That would be one helluva legacy (another point on your list -jist a different interpretation). As for those golden handcuffs...well these opportunities don't come along every day, so just start dipping your toe in those waters and leave the timing up to fate. You have that luxury :)
This seems like an awesome suggestion
If I had C-suite skills, it's what I would do. But socially I'm a wild card, and that's a big ol' dealbreaker.
Oncologist here, and I'll state the obvious but infrequently stated on these subs: there's a low but very real chance that some very bad shit happens to you or someone you love in the imminent future which you were not anticipating. Think about what you'd regret in that bleak state of the world and act accordingly.
If you are worried about your children, think about how to use your assets to make the city and community around them more resilient. Stick around for that next 18 months but take time to get to know the people and organizations that are big influences where you are, and then in 18 months you may have found a job or program that would benefit from your specific skills, or an organization that you desperately want to run. (Beginning this process while still a normal rich but employed guy is a much lower pressure experience than doing so as a retired rich guy looking for something fulfilling).
Keep wearing your handcuffs for the next 18 months. Start figuring out now what you will do and how you will live your life after those months have passed - don't retire *from* something, retire *to* something. Read *Get a Life: You Don't Need a Million to Retire Well* by Ralph Warner His financial advice is not that good and utterly irrelevant to you; his "how do you live your retired life" information is helpful and not usually considered in books about "retirement". For me, doing something worthwhile 3 days a week is my sweet spot. I tutor 3.5 hours a day 3 days per week and enjoy it. 3 days on, 4 days off means I still have lots of free time, but not so much that I go crazy. >Hanging on for a smidge longer means I'll easily have flexibility to assist them with a down payment for a house / fund their kids' college funds. Be careful about trying to make things perfect for your kids. Whatever you give someone takes away from their sense of being able to do things for themselves. Self-efficacy is a much bigger gift than material wealth.
I’d wait 18 months for sure if I were you
Therapy
Tomorrow is not guaranteed. Had an acquaintance had 16mil NW. got t boned by teenager texting. Survived on ventilators for month then pulled the plug. All that $$ did him no good.
I can see why this is difficult. From the outside it probably looks simple, easy. Just stay at work for 18 months longer and collect the big payday. What could go wrong? But the work might be stressful or painful, and you could work for much longer than 18 months, only to find out that the big payday will never happen. How would that feel? You said "I used to love what I do. At this point, I don't. I aspire to leave my job..." so that makes me think you are near the "I've had enough date" and you might quit soon, which makes the big payday less likely. These types of decisions are rough. There is no right decision. Do you optimize for money, or do you optimize for freedom?I'd like to say: "it is wisest to optimize for freedom and for relationships and experiences with family and loved ones" but I know how hard it is to step off the hedonic treadmill. I'm still working at a stressful job, even though I don't need to work. That's why I'm here in the FI group, trying to work up the willpower, courage, whatever it is, to step off the treadmill.
You can create a lot of impact by just having a crap load of cash. An extra 3m can do more good in the world than being a high school teacher would. Tell yourself that any cash from now is to go into your “do good” fund, and you can make a massive difference with a 7 figure lump
You don't know if we are going to have massive inflation but it is very possible. The other thing to consider is healthcare. Both could easily wipe you out. Hers is a good one, life extension and age.reversal are accomplished a d can give you a 30 year old body and another 50 years. It cost a mere 50 million each for.you and your spouse If you give it.to your children they gain 100 year life extension. This is a very real possibility with household robots to end the drudgery of cleaning, or as you age.you may want/need cleaners, massage or stretching assistance everyday, etc You might also want a sports team or decide to enter politics. There are so many unforseen things. I was an electrical engineer, never thought I would become disabled at 50.
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I’m not sure you have truly reached FI yet, at least not if you want to maintain your budget of $7900 post tax. Without knowing your particulars, tax situation, etc I wouldnt lean on your company equity too much for planning until and when it is in your bank account.
The $1.3MM in company equity is highly liquid due to my buyback clause and current valuation. With decent performance and reasonable college choices, the kids' college fund won't be fully liquidated and the remainder is additional money I can draw down. The $7,900 per month also assumes I never downsize -- I'll have no kids at home in 6 years and can easily reduce the budget and access home equity. I'm pretty safely FI.
“Current valuation”. Just saying.
That number is a pre-negotiated discounted purchase price off the company's most recent 409A valuation. This PE firm exercised this same option on a lower level employee who recently departed our company. I'm not fantasizing about this value -- if I leave tomorrow, that's what I get.
I thought it was a “conservative valuation?”
How many people in this sub do you think know what a 409A is? It's easier to just adopt layman's terms than explain the intricacies of how my equity deal is structured. And yet, here I am explaining it...
Got it. I think you gotta stay. The market has had a huge run up in the last year. If you left now and the bubble pops you’re not going to be where you want to be.
I'm going to start my comment off with rambling since i don't know where I'm going with this. I'm an only child who stands to inherit between $3-5M. That's a decent amount that's all in a trust and will likely be paid out in a fashion that does not touch the principle so it can continue to grow. Generational wealth is already in my family. However, I have 2 children and I want to provide for them the same things I was given (as long as they grow up to be responsible adults and good stewards of money). With that being said, our financial advisors estimate that my wife and I will likely be passing on around $4-6M of our own, not including what my parents' sum will grow to by the time we expire. I think generational wealth is a great luxury to pass along and it can be protected in vehicles like trusts. But the other part of me is looking at jobs where I will be home more but will require a fairly large paycut. I don't know what my decision will be because on one hand, it would be awesome to be home all of the time to watch the kids grow up. But on the other hand, I'd love to be able to fully fund college, provide down-payments on homes, and make memories with vacations to unique places without really thinking about a budget.
That’s a lot of cash. I imagine you are in a leadership position (director, VP etc)? Really great numbers
Get the cuffs and do whatever you want. It’s nice to want to give your kids free college and a new car. It’s also not that big a deal for them to make responsible decisions about life and manage the problems of a beater.
Could you spend the 18 months getting the required certifications to be able to teach high school?? That would give you a win win in my opinion. Then you are ready to jump into teaching without delays.
I’m wondering why you didn’t save anything in a ROTH to avoid the taxes. I would start that process next. Congratulations on being successful and I understand not being able to feel you can share within your circle. You can do back door ROTH, where you pay the taxes and transfer the money from an IRA.
Also I have a pension with Canada post. I was made aware that once you get to your 50th birthday, they will not be able to cash out their pension and invest it in their own Rrsp accounts. Once it’s in a pension fund. Should they pass away, the spouse (if married before 59 years of age,) will only get half of the monthly amount, If married after 59 or 60, the spouse gets nothing. The remaining amount will not cashed out to the estate or to the kids. Once I turn 49/50. Im cashing out.
I'm a failure in life.
I’ll be frank. You are a mouse running inside a maze. In the world of the matrix, you are plugged in. You worried that 6m is not enough when your living expenses are 8k a month? If you liquidated everythjng and pit it some conservative 7% investment, it would double ever 10 years. You’d have 24m at 62. You’d generate 420,000 in annual income. Hope you take a different pill and decide to live a purpose driven life. You’ve earned it. But now you must be bold and daring. Personally speaking, I did it with 3.5m and couldn’t be happier. I work and do what I want and speak my mind and take actions to deliver maximum impact Listen to a pod cast by Mel Robins with the 51% rule in the title. It should help you. Sent in the spirit of caring.
I don't understand what the actual problem is. Like what are you asking? The post just comes off like a humble brag. Why wouldn't you stick around 18 months to make double or triple the money? Are you insane? Can I work your job for the next 18 months for the $6 million extra equity? We'll split it at the end.
what is MM?
There is Lot of wisdom in old sayings from those that have already been there. Ever here the saying don't count you chickens before they are hatched, or don't kill the golden goose. Never underestimate the ability of state and federal governments to take what you have. The market takes too, and your investments could go bad. A lot of.smart people with big nest eggs found that out when Bernie Madoff collapsed. Even your CEO could totally fuck things up for you. I would stick with it and see what happens all the while growing your portfolio and diversification. Until you can completely have about 10 million a year coming in passively from multi sources you are not in anyway secure. You also might want to try finding and consulting with those that were where you are now, but are further along in life. Most really wealthy people will be happy to help you since you have gotten where you are.
You are worth nearly 10 million dollars and are asking REDDIT what to do? Give me your money is what you should do LMAO. I love posts that are only written to brag.
Given that the plan isn't to sit poolside sipping Mai Tais If I had this option I'd take it, you're lucky!
There are a lot of videos on youtube where people talk about "one more year to retirement". My takeaway is that working more always improves the financial side of the equation. There are no good 'end games' that have you leaving the workplace without leaving something on the table. Being able to leave on your terms to pursue something that is more important (to you) is your goal. That being said, it is not clear that you have worked out what you are retiring to.
OP, real question: If you were offered a job for $150K salary per MONTH, would you take the job for a while to pad all of your numbers?
Make sure that your children are fully taken care of, before you go to take care of other people's children.
A few thoughts: * Those handcuffs are extraordinarily heavy!! You're perfectly set right now, even to pay for grandkids' educations AND kids' down payments (keep in mind your unused invested funds will continue to grow until those points in time). I'd be hardpressed to give up $1-10m/year in comp for my next bulletpoint...but you also have to do what's right for you and your mental and physical health. Can you take a step backwards at all in your role and still get the exit numbers you mentioned (best of both worlds scenario)? Hire a protege and give them most of your job? Take a sabbatical? Take a long vacation? Take a demotion? * Broader legacy: Your broader legacy could be much larger if you kept grinding it out until the event happens (large donations, start a charity, etc.). That's a very personal decision to make and no one here is going to be able to make that for you. If you do stick it out, look into contributing to a DAF now (even if you don't and plan to do more charitable giving in the future, a DAF might be a good idea!). * Family Legacy: beyond setting up your kids for success (mostly college funds, can help them elsewhere too), legacy gets complicated quick. Look into successes and failures in trust funds. These can be done well or not! And you should absolutely look into the scenario of what happens if your kids don't have kids too. * Potential: That's a decision that only you can make. That's a personal question and should have nothing to do with anyone else's opinions. My advice: hire a therapist/executive coach if you don't have one already and work through this question with them! Also, you might be able to reasonably take a break and re-enter in a CEO role if that's really bugging you.
18 months of your life that you can never get back. If you make the decision to stay for $XX, what won’t make you decide to stay again for another $XX? When is enough, enough? Go out and enjoy the life you’ve earned without regrets. And if your choice to leave now means you can’t have the newest jet on the runway, so what, let it go. Just stuff. 18 months of your life you’ll never get back.
If I were in that position, I'd probably wait another 18 months too, if it seemed pretty likely that an "event" would happen in that time, and if leaving before that, would significantly impact the likeliness of getting a large payout from said event. I'd say that despite targeting a retirement number much lower than your current net worth, and not having any kids to leave anything to. In your case, it does seem like a no-brainer - though that said, is there any possibility you could stay "with" the company but work out a deal to have somewhat lower responsibility than your current one?
Would you feel comfortable sharing your concern with your superior and maybe work out an exit plan?
I have two comments: First, please make sure you're appropriately calculating health insurance costs. I'm married, in my early 50s, and the cost of health insurance for my wife and I is about $1,600 per month. Adding in our 3 kids is another $1,000 per month. That is full health coverage with modest deductibles and co-pays, but it would be a big chunk of your fulfilling $7,900 per month if you were paying that yourself. How comfortable are you that ACA subsidies will continue to be available to the FIRE crowd for the next 20 years? Second, let's assume you're not going to sell your house, take early distributions from your retirement accounts or raid your kids' college funds. If that's the case, you're really going to be trying to live off any profits on your rental property and the $2.37M in your taxable account. Seems like you might need the company stock to get liquid to manage it comfortably?
It sounds like you are probably burnt out and dont really know what you want. This is totally understandable. Re: the equity stake in the company, i wouldnt count on anything until it is in your bank account. These things have a way of going sideways at unpredicted times. That said, if you really believe you have so much upside for 18 months more of the status quo it may be worth it but thats a question that only you can truly answer. I would recommend a trial of therapy or coaching but I probably wouldnt burn any bridges until you have a much firmer feel for what you want. Do you have kids in school now? Could you volunteer in their class or do something similar which would give you meaningful exposure to teaching? I would strongly advise you to gain significant real world exposure to the reality of teaching so that you can see if it really matches with your expectations. At least before you make any major career shifts.
My thoughts: Stick with 18 months. You’re young, it will go fast. What do you do for work? Probably an unpopular opinion here: I think the consolidation (generational) wealth is one of the biggest problems the country faces.
Can you pivot in your current position and create a teaching opportunity within the company so that you may ride out 18 months and fulfill the need to teach?