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by philangist 1683 days ago
I won the IPO lottery and I’m in the middle ground between rich enough to never work again but not quite rich enough for the yachts/mansions/private jets lifestyle. I haven’t worked in 6 months and I’m struggling to find a larger meaning to my life beyond getting yet another tech job. I’ve considered going to college for a math degree, moving to my parents home country, and joining the military (among many other options) over the last few months. Just feeling very aimless so I’ve started reading Russian literature and spending hours on Reddit every day.

27/M (today was my birthday :)

57 comments

This is quite normal. Many who win big in the literal lotteries are worse off. I know reddit is all antiwork these days, but that's really mostly about rights and not not working.

Being a productive member of society is meaningful. I'm from Scandinavia and a lot of our identity is tied up with our careers. Being without a job or any structural social purpose is asking for depression.

GWF Hegel wrote about suffering from indeterminacy. In short, autonomy is inherently social, so ways of life that are merely abstract (i.e. that society does not recognize in terms of existing mores) are void of satisfaction. Satisfaction is only real and concrete through reciprocal recognition. So the "I can do anything" type of freedom is only mere freedom (Willkür), which drains the individual of intersubjectively verifiable self-determination. I.e. you're determining yourself, but no one can recognize it without coercion, and you're unable to recognize it in social reality only in your mind. (And conversely, over-determinacy is slavery.

So even if you don't need to work for money, you might need a job to be able to find meaning in your life. We are a social species that survive on collective efforts.

Personally, if I had won lots of money I would strive to live on as if I didn't.

I think you're too easily taking for granted that having a job makes one a productive member of society.

Evergreen link: https://www.amazon.com/Bullshit-Jobs-Theory-David-Graeber/dp...

> society does not recognize in terms of existing

The hell with this. Society nows recognizes Early Retirment as a status to aspire to. People look up to joung retirees, and this provides a pretty big identity.

The FI movement now put a name and label on it, so the belonging part of meaning is covered.

Doesn’t society also recognize celebrity as a status to aspire to?
Considering the number of depressed people who have jobs, this seems a very questionable view.

    (!a -> !b) =/=> (a -> b)
Nobody said a job was sufficient to ensure good mental health.
Most of these people are forced to work.

I think for me personally a 4-6h workday on 4 days per week would be optimal. It's enjoyable to actually work together with a team on a product and provide a service which people want to use.

Such part time jobs can be very fulfilling if money is not an issue.

Wouldn't there be resentment from the team because they work harder than you or just generally putting in more effort?

Open source might be the right avenue for this type of freedom. Work on something important like Matrix or something

> Wouldn't there be resentment from the team because they work harder than you or just generally putting in more effort?

not in my experience. there are often people around that only do 25-35hours per week... at least in the places I've worked at 'till now.

> Open source might be the right avenue for this type of freedom

with open source, you're always an outside contributor. That might be enough for some - but I doubt that my motivation could keep up long term in that setting.

It's just a matter of what you've been taught to believe is important in life (by culture, religion, parents, peers, etc.). What humans need psychologically is something to keep them occupied and their time structured in some meaningful way, but one doesn't need a job for that - you can practice your hobbies, socializing, taking care of family, or whatever one finds fulfilling. People also need a sense of security and, as you mentioned, peer recognition, but having money fixes both of those quite well. In the end it's all very individual, because the sense of purpose, achievement and self-esteem doesn't deal with some absolute predefined values, but it's relative to your own set of expectations and goals.
What if you can internalize the social mental sphere inside yourself? Giving yourself an honest and just approval when deserved?
If from the Coinbase IPO, you just got out of lockout and you're new to that amount of money. You're probably still near 100% invested in Coinbase and need to divest into something more diversified and less volatile than Coinbase before you can sit on your hands and look at the number in your brokerage account as if it was real retirement grade money. Plus you'll need to pay a ton of taxes on the capital gain.

So don't chill out too much. Divest out of Coinbase, continue life as before and get used to the money. Take your time before changing everything and increasing your spending levels. In a year or so, hopefully you'll have diversified and your head will have cooled from the new money, and you'll be more leveled and realistic about what this money enables you to do, and how to handle your life going forward.

As far as I can tell, it seems like a large (20-50) percentage of people who have a large windfall... end up losing it all because they don't take the time to learn how to handle it.

Good luck and happy birthday!

There's a Ask HN thread, maybe a few, of people who hit it rich and later lost it. The common theme is it's easier to make lots of money than it is to keep it, which is a little unintuitive.
The scenarios where that can happen:

1. Bad budgeting or lack of diversification. "95% of my money was in Enron"

2. Confirmation Bias. "I build a successful company once, I can do it again, but this time with my own money"

3. Hedonic Treadmill. "Flying commercial is so annoying, I'm going to fly private, and figure out how to pay for it later"

Do you have a link to this one please? Sounds interesting!
https://news.ycombinator.com/item?id=20521902

The good stories are around the middle.

Is it really unintuitive? Most Americans only save about 7% of their income IIRC, wouldn't it make sense that they would mismanage most windfalls by default? In recessions, this number jumps up dramatically, proving that it's mismanagement that contributes.
I don't believe anyone gets a windfall by saving 7% of every paycheck either. Those who ran a startup make it a habit of burning through millions a month too. What's really unintuitive for me was seeing that CFAs are terrible at personal money management.
thanks for sharing, storing thst up in the noggin
Not to mention that there's a nonzero chance of Tether bringing down the entire crypto ecosystem (temporarily) within the next year, Coinbase stock included
I'm trying to figure out crypto right now, could you explain why you believe this? Or link somewhere where I can read about it?
Tether has been extremely opaque in what assets they hold to ensure the 1:1 USD/Tether peg. It's been observed that at least as one point they definitely didn't have enough USD-equivalent for it, and they've been issuing new Tether at quite a clip since then with flow on effects to the BTC market.

Now if they actually had this financing in place, this would all be fine - but nobody can find a proper accounting of who they're doing business with at the scale they claim to be doing business, beyond the observation that none of the big US players seem to have any business with them - so what assets are actually backing tether?

https://www.forbes.com/sites/nicholasgans/2021/05/13/tether-...

Note that the vast majority is "commercial paper": basically short term loans to companies with relatively risky backing. The problem is that's all we seem to know: no one knows from who they've been buying these. It might be large US companies with 50 year histories, or it might be Chinese property developers at risk of bankruptcy (at which point international debtors will be the first to lose their money).

Tether is just one of many cryptocurrencies -wouldn‘t its implosion lead to people pulling out and investing their money in other crypto, hence consolidating the market and making every other coin rise?
Would you trade me a dollar for 12 cents? If it implodes who’s going to trade you the other coins for something of questionable value?

Additionally, say you hold 50% tether and the rest in a mix of coins. Your portfolio would be cut in half. How does that result in other coins being purchased if people are uncertain of tethers true value and unwilling to trade for it.

Then there’s the whole using tether as margin for leverage or if your margin is based on tether, and that disappears, your position will be liquidated. Now add the layers of derivatives that are quoted and settled in tether. Additionally what exchanges can you trust that will let you cash out in an event like this? People will run to the doors and liquidity will disappear creating a larger sell off as people seek shelter in liquid assets.

What are the most common reasons for losing it?
The number one reason for folks who won the "IPO lottery" is they fail to cash out/diversify their stock, and at some point in the future the stock price drops dramatically.

For example, during the 2001 tech boom/bust a lot of tech companies went bankrupt in a very short period of time. As a result a lot of tech employees saw the value of their stock/options drop to zero (effectively). The speed in which the bust happened caught a lot of people off guard.

It is generally a good idea to move at least some of that money into a diversified portfolio as soon as possible. But folks often put this off because they don't want to pay the cap gains taxes and/or they think the stock will keep climbing.

I guess I did the right thing: Atlassian IPOed in 2015 at $21, despite everyone suggesting to cash out, I wasn’t interested, and I sold only since 1 year between $180 and $320, and kept 1/3rd. BUT it keeps climbing, $480, so you aways feel like you’re missing something, whether you sell or not.

There is no right way of doing it, you’ll never sell at the top. At least the right moment is when you can use the money for a project.

sell half, keep half (or whatever ratio you're comfortable with)? that way if thing go bad they are not as bad as ending up with nothing and if they get better you still benefit a little bit.
My econ teacher always said to keep the money invested you want to lose. Couldn’t you take out a sum, but keep investing a sum you dare to lose?
Hence GP says 'diversify'. If you weren't an employee, or were one with no related stock in the company, would you buy so much, invest ~everything, in that (or any) one company? No? Well, don't treat holding differently to buying. It's the same, modulo fees & tax.
My econ teacher taught me nothing about personal finance. Is this normal?
Michael Saylor says only invest the money you can't afford to lose.

This is likely closer to reality, if one is cryptocurrency savvy.

I'm guessing lifestyle inflation, divorce, bad investments ...
> As far as I can tell, it seems like a large (20-50) percentage of people who have a large windfall... end up losing it all because they don't take the time to learn how to handle it.

I agree with all your advice, but I think that^'s impossible to tell. The vast majority of people successfully and sensibly handling such things are (partly as a result or even 'input' of it) not talking about it.

I was in a similar circumstance. I drove a city bus in Las Vegas for a year. The experience opened my eyes to many things and changed my life in good ways.
Would love to read a blog post about this kind of experience!
That's good to know. One of my projects is to write up experiences like this I've had.
Please do write this up. What a fantastic experience to learn more about !
I would like to learn more about your experience.
I'm considering something similar (although probably not as large of a lump sum). I want to spend a year~ as a bartender.
Recommend reading "Four Thousand Weeks" by Oliver Burkeman. It's about time management, but not the traditional "how to get everything done" sense. He talks about what a normal person can do with their "4000 weeks", or, roughly speaking, their life. If you do decide to go back to work, I'm sure you'll approach it in a very different way. I'm a lot older than you, but I'm also 6 months off work on a break. I'm doing a lot of non-tech stuff (DIY, cycling, running, reading, adopting two greyhounds). But I am planning on heading back to work soon. I didn't win the IPO lottery, but my house is paid off and I live frugally. I could probably do nothing for another year, but it's time I went back to work. I'm just going to approach it very differently this time around. My father is very old, and I lost my sister three years ago. People matter.
I just read the short summary on goodreads [1] and... color me skeptical...

It reads like a version of "The Celestine Prophecy" [2] but aimed at a middle-aged tech bubble. Could you (or anyone else) compare the two, for a very slow reader to make a decision? :D

PS yes the comparison is probably too harsh but that was honestly my first gut reaction...

[1]: https://www.goodreads.com/book/show/36481028-4000-weeks-a-li...

[2]: https://www.goodreads.com/book/show/13103.The_Celestine_Prop...

I believe you reference the wrong "4000 weeks". That one is by a different author. There doesn't appear to be a Goodreads listing for this one yet, but there is on Amazon.
Do you perchance like to teach? Maybe lectures like traditional classes, but there's a huge need for mentors to young folks with interest in technical fields, particularly in underdeveloped countries (in many such cases merely talking to them in English is already a lot of help!)

I know I'd like to do that, but I've always liked teaching so maybe it's not fitting to everyone.

E.g. I volunteer at a local (Brazilian) nonprofit org as part of my employers' give-back programs and I love it. I try to get (underpriviledged) kids interested in computer science concepts by discussing how they are applied in games. It is all remote (which adds a level of challenge)

I'd believe many such orgs exist. In fact, writing this it occurs to me that putting together a curated list could be a worthwhile effort.

Hey man, long time lurker, first time poster here. I'm also brazilian (living abroad) and interested in doing some sort of volunteer work teaching CS basics. The idea of doing it in my mother tongue to underpriviledged brazilian kids sounds awesome!

I also have my email on my profile, please contact me with a bit more info...

Obrigado e tudo de bom pra vc!

Just a heads up - adding your email allows the admins to see it, but not other users. You'll have to add it to the description so I can see it!
Can I ask you what the name of the org is? I really like to teach, I've done it before, and being Brazilian really makes me want to give back to an institution closer to home.
Please add an email to your profile so I can reach out directly - I shouldn't doxx myself that obviously and if I post the name of the org I will
My email is my HN username on the gmail domain, I've also added it to my profile.
Not that you asked, but just find things you enjoy and do the shit out of them. It seems that keeping the mind busy and fulfilled is a part of a long and happy life. Seen a number of folks fall into a sort of purpose hole when they got everything they ever asked for. It’s a strange thing. It’s sort of like… okay? Now what. We did it. What else is there. But really it’s the same things there always was, just that the external forces are removed :)
I went back to university at 36 after achieving a very, very modest degree of stability in my life. It was one of the best decisions I've ever made. Gave me a completely different perspective on who I am, what I'm interested in. It gave me the skills to start working in a sector I actually enjoy.

My friend, if I had never work again money, I'd just pile up Masters and PhDs.

I‘m wondering what‘s your motivation behind that… Do you just like the sensation of studying so much?

I‘d probably feel empty myself just accumulating knowledge all my life and not applying it to any high impact problem worth solving.

My Ph.D. was far more than 'just acquiring knowledge', though I did plenty of that.

It is also about advancing the state of all human knowledge. Like what the big tech companies promise that you'll be doing, but without the corrupting element of needed it to be immediately profitable. Much less evil.

A good Ph.D. program should be built on solving a high impact problem. I nailed a few of them, including a couple of medical breakthroughs around some pretty serious diseases. Didn't make any money off of it, but did make a big difference to the world.

And after the Masters, the emphasis is not on 'studying' as much as it is in 'teaching'-- you should be teaching others how to think and approach a problem. Again, potential for massive impact.

I would also feel empty just accumulating for myself. But that's not what Ph.D./post-doc is about. It actually sounds more like getting a job at a FAANG where you are paid megabucks to get 6-yr olds addicted or to destroy the internet or to totally co-op open source.

Touché, and thanks for sharing that perspective.

I chose the entrepreneurial path to societal impact for myself, but you reminded me about that a lot of the basic research we‘re all depending on was done by doctorands and researchers.

And just like entrepreneurs, you‘ve got two kinds of PhDs as well…

Many people (myself included) that get PhDs simply love learning. Solving problems is important but for some there is this inner drive to need to learn and master everything. It doesn't preclude solving problems, but it's the acquisition of knowledge that is the internal engine, not the desire to solve a specific problem.
Yeah. I can’t understand the counterpoint to getting PhDs. Do you not want to find out how the world actually is? It’s a never ending quest too.
Teach at the university! It is incredibly satisfying work.
Same age, made $4.5 million in an IPO. Decided to join the military. It was worth it, would recommend with several key caveats. Remember, most FAANGs pay you your tech salary while you’re training. A lot easier to get smoked by a Drill SGT when you know you’re making 10x their salary while doing those push ups :)
American companies pay you to join the military?
Some pay the difference between your company salary and your military or reserve military salary.
What military job/mos did you pick? Sounds like you went reserve?
1. Take up and learn about investing. Managing large amounts of money can be a part-to-full time job, and not knowing key mechanics will cause you to get screwed or be at the mercy of others.

2. Find love but keep your wealth a secret until you're sure they are the One and financially responsible. Love comes undone fast over money, and you'll probably need a pre-nup to avoid getting cut in half if things go south. Easier if your partner is also a professional and has assets which goes back to them being financially responsible.

3. Establish a relationship with a law firm. You never know when you're going to need them.

4. Build those software projects you've always wanted to.

2 is an interesting one because almost every day on /r/relationship_advice there is at least one thread where someone asks what to do when they discover "the one" has kept a secret from them for a long time and now they don't trust them any more. I imagine that response would be different if someone suddenly declared that they were rich, versus that they used to be a sex worker but sudden changes in the relationship status can certainly be unhealthy in a variety of ways.
There's also plenty of couples from different wealth levels doing just fine. I'd say reveal it early, though not necessarily on the first few dates.
I think you can cross the military off your list. If you've made enough money to not work, I feel like you'll get tried/frustrated of the BS involved in a lot of it before your commission is up. I could be wrong though - just things I've seen.
Plus, doesn't the military come with an elevated risk of being killed on the job?
I feel someone should see a therapist if thinking about joining the military out of boredom
I can actually relate to that to be honest. I can't speak for OP, if it's about boredom/fun then it's very selffish. But it might be about making a difference there.

Because military, government etc. all deserve people who are in it for "the best" / purpose alone, especially if that's different from the motivation of the majority of people who join.

There could be multiple meanings here. Do you mean because a big part of being in the military involves dealing with boredom, so it would be illogical?

Or do you mean you think they are joining to be violent? There are plenty of nonviolent MOS. For example, they might want to be a cargo pilot or join the cyberwarfare program.

Same age, also won the IPO lotto, but not enough to not have to work. Just enough to be financially comfortable with any downturn.

I think it might have been the best outcome. Actually on second thought, no, I'd love to not work. Congrats.

Happy birthday!

I'm a similar age as you (30) and like you I've built a decent amount of wealth to the point where I no longer need to work anymore. Over the last couple of years I've had to question what life means beyond money and all the hedonistic pleasures which money can buy.

I don't know how transferable my experience is, but I would warn against focusing on pursuits that are overly self-indulgent. At some point you're going to find there just isn't much more you can want, and you may even find yourself feeling depressed and confused about what your next pursuit should be -- especially if you've always been a highly driven individual like myself.

Instead I've found looking around myself and asking how I can help others has given my life a sense of purpose again. You may not be able to make yourself any happier with money, but you can improve the lives of others. And to be clear, I'm not talking strictly about spending money here (although that is an option), but if you don't need to work anymore simply volunteering your time in a way you believe will make a difference can give your life a huge amount of meaning.

> rich enough to never work again

Congrats... but be careful. Some young people underestimate the amount of money needed to "never work again". If you're not working then you don't have group health insurance. You're in the individual market, which often has crappy insurance providers. If you have a serious health issue, and get into a dispute with the insurance provider, your illness can cost millions. If you have > $10 mils you're probably safe though, assuming you invest wisely.

Thank goodness for Obamacare (at least in the mid-Atlantic US). Before Obamacare, individual plans were absolute shit (my individual plan wouldn't have covered my wife's pregnancy with our first kid... her job's insurance did).

Thanks to Obamacare, individual plans have the same coverage as employer plans. Without Obamacare I couldn't have started my company which now employs 9 people in well paid tech jobs (without a penny of outside investment). I'd be stuck in an artificial set of handcuffs imposed by a stupid legacy system of tying health insurance to employment.

> Thank goodness for Obamacare

Yes, without Obamacare it wouldn't be possible for me to even imagine retiring early.

> Thanks to Obamacare, individual plans have the same coverage as employer plans.

Not quite. The network is usually smaller. Employer plans have a nationwide network. Which means that if you get a rare disease for which the best doctor is in UC San Diego, you can fly over there and get treatment. Most Obamacare plans have limited networks, for example in my area only in-state providers are on the network.

I’m not sure if I agree with your experience, in New York City Obamacare plans are horrendously bad, The coverage comes nowhere near to the crappiest employer plan. I had to hire a Nigerian kid to just call the doctors listed on Obamacare website which accepted the silver plan, and about only 40% of the doctors really did (this was for a delivery). $1400 per month for a mother and a child. I currently pay $1400 per month for coverage in all the US through open access for a full family of four (because I live in a place where Obamacare isn’t applicable so the prices are relatively dirt cheap and allows special deals with mainland insurers to get that coverage most mainlanders don’t get).
The price is probably similar to what the employer pays. It just gets hidden because everyone only pays attention to what comes out of their paycheck. I know a past employer paid $2000 for me per pay period.

Health insurance is bullshit obviously. the costs are hidden and definitely suppress what our wages could be. A government solution would be hard pressed to be worse.

I don't think anyone really thinks that health insurance plans cost $200 vs individual plans being $1400. Just the implication is ridiculous. Our problem wasn't the price, but the coverage. I know my BIL pays $2200 (total, including what his employer pays) and gets excellent plan for him and his wife, whereas us paying $1400 (and this was the same case with the more expensive plans too, coverage didn't change a bit, any doctor who accepted gold, accepted silver too).

My point is, (speaking strictly from a consumer POV) whatever is the reason, the NYC doctors just didn't take Obamacare plans, period.

Oh this is true of insurance everywhere but especially in NYC. Dental, Vision, legal, whatever. Every time (in NYC) I tried to make use of insurance I had limited choices and they were often bad.

In other parts of the country I’ve had more success using insurance.

> hire a Nigerian kid to just call the doctors listed on Obamacare website which accepted the silver plan

How much did this cost? How did you find/arrange it? This is fascinating. When selecting my healthcare I remember wishing I had the time to make so many calls and then just gambled with an educated guess.

I paid him the US minimum wage and that was a bit too much for him for very little work, kinda spoiled him a bit.

I think I paid around $200.

How did you find him? An upwork-like platform? Personal connections? How did you vet for english ability/reliability?

I suppose my fascination is that this seems like a 'platonic' example of globalism in action. But in my mental model of globalism, the ability to engage with its benefits are an exponential function of ability to spend public-company amounts of money.

Obamacare is utter garbage and costs ridiculous amounts of money. It impoverishes poor people far more than it helps. They should've provided a tax credit to people who pay in with it. Instead they just reduce AGI. What a joke. Honestly the best thing Trump did was make that no longer mandatory or face a penalty. It was a rammed through system democrats did just to pat themselves on the back. Quite literally one of the biggest slap in the faces to the working class in a long time.
It sounds like you are incredibly privileged to not have "pre-existing" or chronic medical conditions. For many, the ACA saved their lives and the lives of their loved ones even if the premiums were as universally outrageous as you claim.
This. Little babies born with health issues used to be forced onto government healthcare, and parents had to reengineer thier life to qualify. Absolute savagery.
I know it's super shitty to say this, but the true reality to life is...no they don't. It's a savage truth but genetically your produced a child with a major issue. To see their survival it's gonna cost something.
I wouldn't say privileged, just normal seeing as people born with pre-existing conditions are the abnormality.
Sorry, but anti-health-care supremacists don't get to do everything in their power to sabotage, strangle, and corrupt something necessary, good, and sensible, just to backflip and whine that it's not perfect, not named after their cult leader, and "not hurting the people it needs to be".

https://www.vox.com/policy-and-politics/2019/1/8/18173678/tr...

Why is penalizing people you disagree with (or secretly agree with, but just hate) more important to you than saving lives?

If the net effect is saving lives, improving health, reducing poverty, battling pandemics, fighting quack medicine, and advancing science, then maybe the DO deserve to pat themselves on the back, huh?

not being denied for pre-existing conditions, or being dropped for hitting a lifetime limit, have been a huge lifesaver for many Americans. if one is fortunate to be young or healthy the ACA wont benefit as much. but its a huge improvement and peace of mind for the large percentage of folks it helps
That's not really true anymore though. The ACA made it so individual health plans are really similar now to what you will get through an employer. And no denial for pre-existing conditions, etc.

Fk you money where you don't ever need to work again and* maintain a big lifestyle is a totally different story though. Doesn't mean OP can't take a break for a year or two though.

Even for a serious health issue, millions seems very unlikely. Additionally, while health care in the US is expensive compared to everywhere else, it isn't likely that the premiums for a single 27 y/o would be the deciding figure in "can or can't retire".
See 60 minutes story on hospital bill for covid. The patient died. Bill from the hospital for about four weeks of his hospital stay came to a little over $4 million. https://www.cbsnews.com/news/covid-19-deaths-families-60-min...
He won't stay 27 forever.
No, but people tend to spend more earlier in retirement and he can plan for it. Planning for rising premiums as a single person is easy, planning for a family if he ever wants one is more difficult.
I was in that middle ground and didn't like it. The worst thing is it was tremendous fun to get there... but not enough motivation to do it again without that incentive.

People who find meaning in being rich, enjoy being rich.

I kind of think riches are an illusion - you should just go directly to whatever you find meaningful in the first place. Which might include a lot of experiences to find out what that is. Essentially: living.

You can still do that - although having to do something is very motivating, even if we don't like it!

There's an additional problem though. What if you've found a type of work that you do find meaningful and interesting, but you just don't want to spend 40 hours of your week doing it, now that you "don't have to". It's hard to fit back into working life if you only want to do it, say, 20 hours a week. Some part time jobs exist, but they're the exception.
That's where I am currently. I don't mind working and enjoy it often times, but I don't have need to work for financial reasons. Finding ways to serve as an advisor/consultant doing meaningful work less than full time is REALLY difficult in my experience.
Congratulations. I was exactly your age almost 20 years ago and in a similar situation. The dotcom crash was just breaking and partly by luck and partly by judgement I had chosen that moment to exit and divest myself of those shares. My advice would be that you do the same, get a good financial advisor, stay grounded, take care of your future and lock that down, then think about what you want to do next. Spending hours somewhere like Reddit will rob you of the time you have. Ultimately I switched to investing in startups before eventually returning to “the trenches” myself when I was ready. Good luck to you.
How do you get a good financial advisor if you have few contacts in the space?
Consider going back to work, but be ultra selective.

I've worked with a few people who can afford to retire, but find themselves happier showing up to work everyday.

Also, consider YC's founder matching network. Let someone else figure out what the product is, how to sell it, and you just do the bits that you enjoy.

Open source is always looking for more people to work on it.
I should add that open source is always looking for more people to fund it too.
My father met a guy like you, he'd become a maintenance man working for a local government and went around mowing lawns, trimming hedges, etc. after a career in investment banking, just for something to do and to get outside.
Happy B-Day!

Looking for external sources of happiness is likely a losing battle. Keep your eyes open and you will likely see somewhere to be useful/maybe even create something that both helps others and makes something for yourself to get to the yachts stage. In the mean time, try working on relationships around you and maybe volunteer/give back with something more valuable than money - yours skills and experience. Good luck!!!

I’d consider studying philosophy.

When I had questions, I ended up changing from chemistry to philosophy in undergrad (before dropping out after realizing no one had the answers). Despite the aforementioned realization, the grounding in Plato, Aristotle, Kant, Nietzsche, Wittgenstein and a few others gave me fertile grounds to later plant seeds of wisdom from thinkers and artists from every walk of life.

I wish I could help you with the struggle, but unfortunately, like most learned things, it’s something that only you can do. If you ever want to, I’d be happy to chat seriously about what it means to be human, beyond making money, any time.

From one sick bed to another: best of luck, and happy birthday.

If your interest in moving to your parent's home country is not brand new and therefore it's more than something you're just beginning to consider, jump on a plane "tomorrow" and start reading Russian lit and spending hours on Reddit there. This assumes you haven't spent a ton of time there in the past because if you haven't then you will find immediate meaning living there. And if you decide to do one of those other things, or you just feel like it wasn't the right move, you can immediately fly back! No risk. Don't wait. Please. Just book a ticket now.
I don’t know op’s situation - but visa/green card is a big monkey wrench in those plans.

Also consider the wealth expatriation tax of your host country-they can really sting.

Good points. I was mostly thinking that instead of sitting wherever they are surfing Reddit and reading Russian lit they could be doing that in the one item on their list of potential next life steps where there's almost zero risk of getting into a situation that is difficult to get out of (they said they have a long list, but of the ones mentioned that one is "easy" to start doing today and ending tomorrow without complications).

Re taxes in particular I would guess there's no risk of hopping on a plane today and figuring that out later. As much as everyone likes to think governments are sitting there waiting to shout "got ya" it seems unlikely that any single government starts putting you on a tax watch list as soon as your passport is scanned at the airport.

28/M myself, and if I ever ended up with that kind of money, the first thing I would do is focus on my health. I'm very overweight and out of shape and never seem to be able to muster the motivation outside of work to do anything comprehensive about it. I'd love to just be able to quit and consider fitness my full-time job for a year or two.

Depending on exactly how much I made, these are daydreams I've had before:

Start a "company" that focuses purely on open source contribution. Pay people tech salaries just to work on open source projects they care about. My main intent would be to focus on areas where no decent open source software exists or is dominated by a small number of complacent companies that consider it a license to print money.

Learn how to teach and mentor kids, then do it. My mom is a high school computer science and math teacher, and I always wonder how much more effective she could be if funding for equipment wasn't an issue. My students would have access to whatever I thought could benefit their education.

Be a stay-at-home father. My mom was a stay-at-home mom until I turned 16, and my dad worked from home when I was 8 through 12 (the years following the dotcom crash) I started learning to program and got into robotics at 8 years old and I don't think I would've been nearly as successful starting at that age if I didn't have access to both of my parents pretty much constantly. If I ever have children, I would want to give them the same or better. Try to guide them along whatever piques their interest and enable them to access the resources to do well.

My personal view on life is that there really isn't any higher meaning to it. I'm content to wander the Earth finding and doing interesting things until the day I die.

It's awesome that you have such concrete dreams. Please don't wait until you're rich to pursue them, especially dropping weight and becoming healthier. That's one of the best things you can do for yourself in life.

I was a fat kid who managed to lose the weight around ~16 and kept it off till my 30s. I'm 36 now and independently wealthy - much chubbier now than in my 20s. I can tell you that money and lack of worries doesn't make finding the motivation to see a large weight loss through any easier. I go through periods of working out/playing sports for 3-4 hours a day, but if you like eating, it's easy to super compensate and continue to put on weight. I always seem to manage eating one more croissant.

You don't have to do it all at once to become healthier either. any year where you trend downward, even by half a pound, is an improvement. It doesn't have to be all or nothing. Again, easier said than done, but you don't have to be comprehensive - just 1% better every day.

Happy to chat with you about weight loss and health if it would be helpful: zemvpferreira @ the old gmail.

Try Brazilian Jiu Jitsu, BJJ. Best sport for software engineers, because you constantly have to solve hard puzzles. You never have to worry about motivation again to do sports. I started it 6 months ago. I'm still in the very very beginning, but I can't imaging not showing up in class, it is so fascinating. In order to get better I lost ~30 pounds, started eating better, etc. Changed my life.
There are lots of ways to rewardingly expend your time without worrying about money. Volunteer. Do open source stuff. Get into dungeons and dragons. Have kids, or get into Warhammer 40k minis, if you want to go broke.
My goal when I reach this hopefully before 60 or so:

Buying a farm, building a nice private park, building Rome style bath, japanese onsen and having space for family and friends so they would like to visit me because it's very nice.

But sure you need the interest in wanting to design and build your own house, park, pool etc.

Get into gardening. It’s the ultimate leisure activity for people with too much time. And it’s a natural segue to fancy cooking which is also a fantastic time sink.
If you have the time and feeling lost, I suggest you to spend 10 days for a vipassana meditation camp. They have centers worldwide. Happy Birthday btw!
I do not recommend vipassana unless you've done a _lot_ of meditation before. 10 days of complete silence is a massive strain. I did it, based on little more than a recommendation like this, and had a bipolar episode (no history of bipolar or serious mental illness before). My story [0]

[0]. http://livingvipassana.blogspot.com/2010/02/bipolar-chronicl...

Hey thanks for sharing this! Very interesting. It sounds in many ways similar to my first and second-hand experiences with psychedelics and stimulants.

Also very helpful to hear someone sincerely tout anti-depressants. All the people I personally know have had mediocre to bad experiences with them, so it's nice to hear the other side of it.

Vipassana changed my life for the best. Since my first course, I did a few more, some 10 days, and some 3-day courses which are available only for people who already did the 10 day course.

It made me a better entrepreneur, better father, better spouse.

Like the commenter above stated, there are people who have psychiatric breakdowns following or during such courses. I don't think the Vipassana organization is doing a good job making this information transparent. But, from my anecdotal experience of over 20 years of courses, these cases are very few and far between.

Vipassana is great. I went to a retreat in 2017 that I fully credit with putting me on the path that led to this current situation. I've been trying to enroll in another 10-day course for the last year, but they fill up fast and I've yet to make it off the waitlist.

https://www.dhamma.org/en-US/courses/search

Happy birthday! No great answers to meaning of life, but work focused on societal contributions helped me. In 2009 I was burned out on consulting for banks and telcos, switched to focusing on public sector challenges. Lots of needs for purpose-driven design, dev, product. Also coaching and mentoring, especially for social innovation. Have yet to hit lottery, and make less than I could with industry clients, but better for my sense of making a difference.
When people say "enough money so that they don't have to work anymore", what kind of money are we talking about here? 1 to 10M? 10 to 20M? or what?
In general you can leave your money in the stock market and take out 4% a year and expect that to continue forever. Obviously there is no guarantee on that but it has held true for 60+ years. If your expenses are 40k/year you only need 1M to retire. 20M would get you 800k/year.
I doubt 1M is anywhere close to the figure. And 40k in expenses? What kind of life would you be living? My rent alone is more than that.
It depends on the person.

There are a lot of people in the world who make $18/hour. This would cover their expenses. On the other hand someone like Bill Gates or Jeffrey Bezos have much higher expenses to you.

Apart from philosophy mentioned by the other poster, you can also read into psychology. Some branches in psychology deal with the question of how to live a fulfilled life, eg. positive psychology [1] and humanistic psychology [2]. Also Buddhism has similar goal and teachings interleave with these psychology topics [3].

To start, you can pick a Psychology 101 textbook (I like Psychology and Life [4]) and then read the people and bibliography mentioned in these Wikipedia articles.

[1] https://en.wikipedia.org/wiki/Positive_psychology

[2] https://en.wikipedia.org/wiki/Humanistic_psychology

[3] https://en.wikipedia.org/wiki/Buddhism_and_psychology

[4] https://www.amazon.com/Psychology-Life-Richard-Gerrig/dp/020...

Agreed. On my journey to some sort of personal meaning I ended up going through psychology, physical sciences, philosophy & meditation - roughly in that order with poetry and literature interspersed…

But understanding life has, in my experience, been similar to the hermeneutic circle: to understand a part, you must understand the whole, and to understand the whole, you must understand the parts…

That is: the entry point is here - learn about the world and about how humans think about and perceive it. Start anywhere, but start.

*edit: I forgot to add also history. It also helps to shed light on the different meanings people have discovered over time.

What were the events leading up to getting such a big equity pay out?

What # employee were you?

Was it options/RSUs?

What % of the company do you have?

How long did you work there?

I ask because I am at a series B, and I'm very optimistic for our future. But I am only employee #100 or so and don't see a big payout for me barring a multi billion dollar exit (a little too far fetched). I'm just curious how it all goes down for those lucky employees.

I think you are in the sweet spot. Equity compensation drops fast for early employees. Roughly, the first employee might get 1-2%, but by employee #10 it is down to 0.25-0.1%. At that level, you would still need a billion dollar exit to get into FU money territory.

And keep in mind, at the early stage startups salaries are often lower and the startup is likely pre product market fit. So it is much more risky. Employee #100 feels like the sweet spot because it likely means the startup has found product market fit and is hitting the accelerator re growth, but you still get a taste of early employee equity.

Of course this is just in terms of maximizing "IPO lottery" potential. If you are trying to maximize probable net worth, FAANG probably wins due to higher compensation.

Thanks for that insight. While I can't say what mine is, but your ranges mean I'm OK. I see it as a lottery ticket, you need a billion for someone with say 0.1% to be worth a million, and that is assuming no dilutions.
Also what % do you have out of interest? I'm outside the US so I feel my % is less than you'd get at US startups that generally compensate better. Obviously % isn't everything but it's a metric to track.
I feel you're on the right path, reading and learning are good ways of finding things you'd want to give your time to. (Although there is that feeling of aimlessly letting time pass in part of the Russian literature which might resonate with your own condemdrum - although it's liked to a very interesting political context) If you're lucky enough to set aside the "How am I going to get enough money to live the next X weeks/month/years?", it frees out that much time to answer the much more interresting questions : "What do I love enough to spend all this time time doing ?" "What would I like to understand and/or change about the world?" Volunteering to causes you discover you care about, be it open source projects or walking dogs for old people or anything in between can feel great!

Happy birthday

I'm guessing that you don't quite have enough to really commit too much to this, but have you considered spinning up a new start up?

I've been working at startups for decades but haven't been in the right place at the right time (no complaints, I've made a few hundred grand from options and I still may make more in the future) however I've worked with a number of people who have hit home runs.

Only a few of them have gone on to build their own startups from scratch though which is somewhat disappointing in my eyes. Of course, it's their choice but if I'm ever it that position, I'd definitely fork a new company as soon as the dust settled.

So. . . is it practical for you to start a new company and have you considered it?

I highly recommend fatfire.reddit.com.
Happy Birthday! It appears currently you own just virtual money. ASAP get in contact with some private banking (those that represent rich people), they know how to lower the financial risks so that you can keep this fortune. Think long term, so do not burn this wealth on stupid items (like luxury cars) yet.

New friends can be very costly, indeed! Good advise is priceless.

Advise given by other people? Think: What is their financial status? Do they work with these type of questions? Just ask: What would they do with 10k of 100k. Most will burn it, short term! = WRONG

Like I never give medical advise, because I only finished first aid class.

Probably quite fun to have a small business / startup where you are the boss and hire a few people to solve some problem, maybe related to your previous employment but a niche they didn't cover?
This is quite literally my dream. FIRE, then scratch some niche itches of mine solving deep problems without ever worrying about profitability.
Same here, but without the meaningless feeling. Started like you, and quickly 6 months became two years. Now I have two kids that fill my day routine. And I too read philosophy and reddit a lot.

don't be sad.

Take up martial arts. That's what I turned to after a windfall. I only stuck with it a year but it got me in the right frame of mind to continue feeling ambitious.
Getting everything you want can be a curse! My belief is that humans need to struggle towards getting better and things. Maybe take up chess?
Don't take up chess. it will consume every bit of your free time and give you a new sense of purpose, with lots of frustrations on the path... ;)
You could consider angel investing too.

Edit: and travel the world. Maybe travel the world and angel invest ... startups outside the US would appreciate it!

Find love. Make a family.

But first, you must shed al appearance of wealth, and don’t ever let anybody know about your money until your babies need it.

Find something you don't like about the world and try to fix it. Your financial situation gives you a lot of freedom to pursue either tough projects or thankless (money wise) projects like open source. For me there's no better satisfaction than knowing I contributed something to make the world a better place
Happy birthday! Man am I jealous, I think I’ll have to grind away all my best years at faang or worse.

I also love Russian lit, so so checkout Oblomov and Tolstoy shorter novels like the Death of Ivan Ilyich. I think you’d really like the japanese book Musashi as well (or the incredible Vagabond manga adapted after it)

I thought with fang you can retire in 10 years or so.
I think people overcomplicate this. Pick something you want to do and then do it. If you don't know what you want to do, then finding what you want to do is what you want to do. You have the luxury of choice, use it.
Don't pick the military!

If you have money, it won't be fun. And it's hard to un-do.

I started my life as a carpenter. I loved it and would go back to it if money wasn't a factor. I'd love to be comfortable enough one day to flip/lease one house a year and do all of the work myself.
Invest in my startup :D haha joking

Great one, I would recommend not taking too long to get back in the game of goals as they keep you moving forward, also maybe start looking for a life partner if you haven't done yet.

You could do worse than Russian literature. I did the opposite, moved to Russia instead of pursuing a career. Looking back, your order of doing things makes more sense...
Congrats, could you give a ballpark figure what is considered rich enough nowadays?

At 27 maybe you should look into spending more time with / starting a family?

consider starting a family :-)
Ha! I've considered it and if I found the right woman and we had a relationship that was in the right place I'd definitely do it. But starting a family seems like one of those 'slow and steady wins the race' type of situations.
You don't know who you are until you've experienced the stress of a family and little kids.

Even if I didn't have to, I decided to get a job while having kids to maintain sanity and use the paid paternity leave. Now that the kids are older and I feel like I have a brain again, I'm back at doing what I like: building online businesses.

I highly recommend pursuing family, but you need to be careful in your situation. Getting in a relationship on a lavish lifestyle is a good recipe for a divorce later on. Once I started looking (~at 25), I was extremely blunt in what I was looking for and that helped screen things considerably.

I personally decided to start a family without marrying because marriage laws are pretty unfair towards men where I am and create an incentive towards a divorce and lies just to extract money from the other part. You don't know how your partner will turn out in 10 years, so better safe than sorry. We're still buying a house together and splitting 50/50 irrespective of income / savings. That should make sure there won't be a wife maintenance for me to pay in case we split up and that I won't lose 50% of the house. We also have wills to make sure we have guardianship of kids and access to money in case someone dies.

So what would your advice be? Delay having children? Not have children? Only have children if the mother is prepared to do most of the work raising them? Something else?

It seems like having children is something you may enjoy in 30-40 years - or rather will potentially prevent feeling miserable and alone in 30-40 years. But in the short term - at least 2-3 years, but likely much longer - it can be quite miserable.

Now, given that we don't know how long we get to live and what sort of health we will be in, time when you are younger seems more valuable than time when you are older. That would suggest that having children is often a bad idea, unless you strongly believe that you will enjoy the whole experience. But then, imagining what my own parents' and grandparents' life would be like today had they not had children, it seems like it would be far worse. But their circumstances were very different, too.

I have some rich friends who had 4 kids in a short time span. It certainly gave them a full time job. They seem pretty happy.
For many of my acquaintances, starting a family was a jump in the deep end and sink or swim.

As for end results for child and parents, I am really unsure whether slow-and-planned beats random-pregnancy-and-shotgun-fatherhood. Both succeed and both fail.

If you want to try angel investing in something meaningful, I'm happy to pitch you my nascent Biotech project...
Helping people in need is always rewarding.

You don't have to do it with your own cash.

Lucky you! A lot of us older than you don't have that luxury :)
what about "meaningful" work, like at the internet archive or Allen Institutes or something -- smaller paycheck, possibly impactful work
I also got there a few times, but always got robbed.
College sounds fun! Do it!
Happy Birthday!
happy birthday!!