Did you win the game? Have you stopped playing?

There’s a FIRE adage that when you’ve won the game, you should stop playing. There have been numerous examples of people who had nothing, YOLO’d to get double digit millions and instead of cashing out they kept on doubling down until they lost it all.

So, for those of you who won the game, what did you do? I’m guessing you didn’t take the safest route by moving everything to cash and drawing it down.

So what’s the psychology here? Why do we still take on risk that we don’t need to take on? How do we rationalize it?

I went spending it on polymarket and my local casino cause I can’t stop playing. Also bought a bunch of BTC.

I think it’s just a case of it being hard to change habits once you make them. Maybe in addition to making number go up being a very addictive life goal for some people.

If you got addicted to gambling with options, it’s very hard to stop. If you made a ton of money with a great business, then given the odds of a business succeeding, you probably like working on your business and you did get used to it?

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I think it’s more of a Boglehead adage, the FIRE community seems to be way more into stocks than bonds. I haven’t seen Mr. Money Mustach advocate for anything other than skillset and stocks (but I haven’t followed him lately) and ERN’s longer safe withdrawal rates table points at stock heavy allocations having better chances of a better outcome.

  • Jim Bennett: I’ve been up two and a half million dollars.
  • Frank: What you got on you?
  • Jim Bennett: Nothing.
  • Frank: What you put away?
  • Jim Bennett: Nothing.
  • Frank: You get up two and a half million dollars, any asshole in the world knows what to do: you get a house with a 25 year roof, an indestructible Jap-economy shitbox, you put the rest into the system at three to five percent to pay your taxes and that’s your base, get me? That’s your fortress of fucking solitude. That puts you, for the rest of your life, at a level of fuck you. Somebody wants you to do something, fuck you. Boss pisses you off, fuck you! Own your house. Have a couple bucks in the bank. Don’t drink. That’s all I have to say to anybody on any social level.
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I guess if you hit the jackpot, you’re way above the number you need so it would be a very small risk.

But then the paradox is because you have way more than you need, it makes more sense to have a fairly high risk profile (since you can afford losing a large amount of it).

Well, this is where I can see having a split strategy:

  • You create your fortress which secures your budgeted spending: paid off house, cash buffer, bonds for income/drawdown
  • The remainder could be invested with more risk

I guess this depends where you are. If you are still accumulating, yes, you might want to go with stocks for a faster ramp up.

I’m talking about the situation when you already have more than enough to cover your budgeted spending using just bonds/cash.

ERN did his modelling for the situation of someone withdrawing from their account. One of his motivations is that a 30 years time horizon, as studied in the Trinity study that gave us the 4% SWR wasn’t enough for the retirement ages targeted by FIRE and he wanted to see what would happen on longer time horizons.

I recommend reading the series: The Safe Withdrawal Rate Series - Early Retirement Now

Part. 1 is the one that interests me the most: The Ultimate Guide to Safe Withdrawal Rates - Part 1: Introduction - Early Retirement Now

He came up with this chart which shows that when decumulating, higher stock allocations (75% and 100%) allow for bigger chances of success or higher safe withdrawal rates for the same success rate:

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Hey, we’re running in circle. Why start a new topic every other day trying to find a meaning of life once you solved the money problem. Or even before that.

It’s not a money problem.

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If I only need 100k per year, almost anything would work to cover 100y of expenses. But my point was more that with this amount, you can simply put it in anything with expected long term positive return (100% world equity for example), even with high risk/volatility, you’re fine. (Even with no expected return, as long as it cushions the erosion over long term you’re fine, 100% gold would work)

(In practice 100% cash doesn’t make sense tho, short term sovereign bond will at least avoid inflation)

This is a good point. Looking in isolation, you would say stocks are more risky, but maybe diversifying a portfolio could reduce the risk overall. e.g. moving from 100% cash to 10% stocks, 10% bonds, 10% real estate, 10% commodities, 60% cash/bonds could give you a return where the worst-case scenario return is still higher than cash.

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To clarify: I’m talking about the scenario where you have enough that the 0% stock option already has a 100% success rate and isn’t represented in this table.

Yes, but that’s the same. 100% is 100% (to be fair it’s not exactly in that table as there is rounding).

As I understand your question from an investment (not psychological) perspective, it is “once you have reached far above that 100% threshold, shouldn’t you squirrel that 100% away to make sure you don’t fall below it anymore?”

Edit: It’s a pretty long post so I’ll use dropdown headers. /Edit

The financial side of things

The answer I get from the table is: if you do, stocks are a legitimate way to do it (i.e. squirrelling away doesn’t necessarily mean using assets traditionally considered as safer - though you can and maybe should use them anyway as they may match your ability and willingness to take risks) and if you do use stocks, it allows for that amount squirelled away to be lower.

Now, you may consider that historically backed 100% isn’t safe enough and that you want your assets to guarantee your future financial wellbeing due to their inherent characteristics alone. It may get close to it but you can’t reach 100%:

  • fully paid off real estate is subject to taxes, some non insurable risks (war among others), insurance premiums which can rise and changes in legislation. It can’t be used to match your consumption beside the big part consituted by lodgings.

  • longer term bonds are subject to interest rate risk, inflation and default risk (even sovereign debt has been historically defaulted upon in some extreme cases).

  • shorter term bonds and cash are subject to inflation so there’s no guarantee that the amount you’ve squirelled away actually covers your expenses for the time you expect it to. You’d have to significantly overshoot the target (which if you’re far over the “enough” line, you can but hyperinflation can erode your buying power very quickly).

Which leaves me with my personal conclusion that having significantly gone beyond “enough” doesn’t change the equation on a pure financial level. What used to work is still what works, you still have only one big bag of assets and compartmentalizing it (putting aside what feels like allows you to cover your needs) is mostly a psychological endeavour.

Caveats could be diversifying political risks by holding assets in different countries (flag theory) and legally segregating assets by puting them in other legal entities, protecting them against bankruptcy (though personal bankruptcy would still have your holding of these entities at risk, it mostly allows for bankruptcy from what one of your companies is doing not to expand to your other assets).

The psychological side of things

I don’t think there are high chances the psychology would actually change.

Someone getting 100M all of a sudden has it happen for a reason they are likely to attribute to their own skill. From that point, that skillset should both allow for them to get more and getting away from it would actually constitute a risk as it would be terra incognita and would not benefit from the experience they have built throughout their life.

Getting a huge inheritence is probably the “easiest” to deal with, though not necessarily easy either. The heir may have expected the inheritence coming and then again, their own personality, upbringing and temperance would probably be the deciding factors. Someone grounded would probably make plans for what to do with their assets when they’d get them and avoid overspending them or throwing them all in risky ventures. Someone on the entitled or overconfident side of the spectrum may not use any time to try to preserve some of the wealth and loose it all anyway.

People with huge incomes, most notably successful athletes or rockstars, are experiencing a huge change in their life when their career shifts from providing a lot to not providing that much if any. They’d benefit from early planning but when that would occur, they are 150% invested in their career that demands everything they have out of them and money is plentiful. Moreover, success draws people who want to benefit from you around yourself and bad advice may abound.

People who get it on gambling (lottery tickets, betting, yoloing on leverage on that one asset that went to the moon) both are subject to the thrill of gambling and probably have a very hard time changing mentality once they have achieved way more than enough. If they set part of their assets aside, gamble the rest, loose all but the assets they have aside and can’t gamble anymore, are they likely to think “alright, I’ve had a good run, time to live a good normal life from now on” or “hey, I bet I could 100x that amount I have aside if I just put it on that one horse I have information is likely to win its race” ?

One exception would be the people who have overextended their risk tolerance while growing capital and would benefit from tuning things down to sleep well at night. For these people, I think the damage to their mental wellbeing that may result from being overexposed may be a significant risk and I’d advise they revise their allocation upon reaching “enough” rather than after having let it ride to way, way more than enough. If the way, way more than enough part happens all at once, then yes, your need to take risk has fallen, revisit your asset allocation.

Bottom line

My bottom line is it’s more about building temperance and a poised outlook than stricktly asset allocation or setting assets aside.

With temperance and a poised outlook, one would adjust their investing strategy as it goes, at all stages of life, and be better set to take good decisions as to what to do with their assets if they reach way more than enough level.

Without them, it’s very unlikely one would be able to set aside assets when reaching way more than enough level and to leave them untouched if they suddenly lost their other assets.

The wise man still wants to revisit their risk tolerance regularly, in particular:

  • their need to take risks;
  • their ability to take risks;
  • their willingness to take risks;

and adjust course whenever necessary, after having taken a broad outlook, revisited why they had chosen to take the course they have taken until then and pondered upon it.

Focus point: Invest in wisdom, knowledge of yourself and temperance above anything else.

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A reminder that relying on US numbers can give a false sense of security. Many European countries have examples where 4% would have lasted less than 10 years. Japan shows an example with just 3 years. Safemax can be as low as 0.47%and less than 2%.

Now war is often the major driver here. Maybe something to bear in mind when we have issues like Russian aggression and potential entanglement in Iran to consider.

History might give further lessons:

  • Don’t put all your eggs in one basket, diversifying across counties can help avoid disaster in one
  • Diversify across assets, stock markets can collapse to near zero, currency can become worthless, bonds can default. Spreading your risk across categories helps avoid concentrated risk in one
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While I’m not surprised by the results, some of these charts sometimes use local markets of stocks (i.e. the SMI or SPI for CH). What is the portfolio composition assumed for the retirees on this table (you can just point to the source of the table and I’ll check myself).

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Google for Dr Pfau. He did a study to look at international variations of the Bengen study. I’ll see if I have a link to the PDF still.

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People (almost) always want more. In my case, a very serious health scare woke me up. Once you have a health issue, that becomes the ONLY thing that’s important and you’d give up everything for it.

So, I’d say, stop playing doesn’t mean no longer wanting more, but it should mean: not killing yourself over it if you don’t have to. Time off full-time work (and now reaching an age where life can’t be taken for granted) has opened my eyes to that.

There’s an interesting anecdote (not sure if it’s true) about an anon survey of Olympic athletes which were asked “would you cut be willing to cut your life expectancy by 30 years if in return you’d be guaranteed to win a gold medal at the next Olympics”… it was astounding to read how high a % said “yes”.

The difficulty is of course that some people (incl me) are wired to aim higher all the time and this is for a large part what gets you the success you have in the first place.

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It isn’t the gold, it’s leaving a mark on history. That is the purpose of their training and career/life.

At the same time, it is easier to be willing to trade 30 years of life when we’re young and have a goal of getting what we’d get in return rather than when we’re older, our chances of reaching that goal are behind us and we are very much closer to death.

I wonder how 50+ years old former athletes would answer the question of “would you trade the rest of your life and die tomorrow for having won 1 more gold medal in the Olympics”.

Edit: also, for them, the proposed trade is a very real part of their life. The training they go through and the potential supplements they take are likely to be taking years out of their life.

This, Musk/Bezos are also good examples of this. Making another billion doesn’t mean much for them I suspect.

Re Olympic athletes, imagine how crushing it must be to then see somebody like that swimmer Phelps win 28 (!) Olympic medals.

The achievement to win a gold (in most sports) is something I admire. Not because e.g. running 0.01 second faster is particularly great but because of the monomaniacal nature one must have to commit to the hardships, discipline, etc. to be that bit better than everybody else. I do often find myself raising my eyebrow though when former athletes don’t move on with life afterwards and for the rest of their life just stay hanging in “I was once great” as their life story.

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