A Gaze at Windfalls Past

Thoughts on not having gotten rich quick

I’m not particularly old, but I’m old enough now to have seen multiple opportunities to get rich quick pass me by.

I think it’s worth talking about.

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Bitcoin. Etherium. NVIDIA. Gamestop.

These are some of the windfalls I’ve personally seen happen, in real time. They’re ones that, theoretically, I could have participated in.

I didn’t.

Whenever I think about them, there’s a flash of -oh shit, I missed my chance, that was it, I could’ve been done with this whole working full-time thing and I didn’t, and now I have to spend years slowly saving up money for retirement, when the opportunity was RIGHT FUCKING THERE and I missed it, how could I be so stupid-

And then I cut my brain off, because nothing productive or useful comes out of the recriminations of hindsight.

Of course, cutting off one’s inner monologue does nothing to stem the emotional tide. Each of those opportunities, when looked back on, feels like something I missed out on: a party I was invited to and didn’t attend and later found out was awesome, and now I’ll never be part of the story or get to reminisce fondly on The Night That Changed Everything.

What do you call the Fear Of Missing Out, after you’ve already missed out?

ROMO - the Regret Of Missing Out?

MOSIH - Missing Out Sucks In Hindsight?

FYCAGAYNGA - Fear Your Chances Are Gone And You’ll Never Get Another?

I don’t know, but I’ve got it.

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Life would be so much better, if I’d only participated in one of those windfalls.

All the worries I have about saving up enough money, all the stress of going to work every day, all the petty bullshit that life throws at me - all of it would be gone, washed away in the security of finally having enough.

…but that’s not quite right, is it?

Being sufficiently wealthy to live off of my investments would be a huge boon, yes, but it wouldn’t magically fix my mental health. It wouldn’t give me a partner or a family.

It wouldn’t erase the stress of maintaining relationships with family and friends, or give me delicious healthy food to eat whenever I’m hungry.

I’d still have to do laundry, brush my teeth, workout, take my medication, etc.

Really, the only thing that’d change is that I wouldn’t have to work full-time anymore. I think. It’s difficult to estimate the kind of wealth we’re talking about here, and how much I could have realistically made. One to two million is all I’d really need, and that seems plausible, although I haven’t run the exact numbers.

I have a feeling that doing so would only make the regret worse.

Still, since work is usually my primary source of stress, maybe that would be enough?

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There have been two times in my adult life I haven’t worked: once during the pandemic, and for a period afterwards when I took a sabbatical of sorts, living off of my savings.

I remember both as some of the happiest times of my life.

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Could I have really participated in those windfalls?

It’s easy to think that I could have, in hindsight.

(Everything’s easy in hindsight.)

When it comes to the cryptocurrencies, maybe. I am technically inclined, and though I don’t currently know how to operate a cryptocurrency wallet, I’m sure I could have learned.

Of course, plenty of cryptocurrencies have also been scams.

There’s also the issue of how much money I had at the time, and what percentage of it I’d have spent gambling on the blockchain. Those are real concerns.

(I tend to be risk-averse by nature. When I try to be honest and not fool myself, I realize I wouldn’t have gambled a large amount of money on a cryptocurrency. I don’t go all-in with real money.)

What about Gamestop?

I could have jumped in, the instant I heard about it. I had enough money at the time to do so.

I didn’t. I’m not sure I even regret it, considering just how crazy it all was. Also, unlike the other opportunities that relied on assets increasing wildly in value, Gamestop was, as far as I understand it, a bubble. Get in low and ride it up, hoping you sell high before it pops.

I have no experience with timing the market. Gamestop could’ve been a windfall, or I could’ve lost every penny I put into it.

I’m not the kind of person that can tolerate that level of risk.

NVIDIA, on the other hand.

That one I should’ve seen coming.

(I could have seen it coming. It was technically possible, given my knowledge of the world, to see it coming. If I had thought to myself, “Given the course I expect the future to take, which stocks might increase massively in value?” and then acted on the resulting information. By betting a lot of money on it.)

It’s also the most recent windfall.

The freshest SOMO - Sting Of Missing Out.

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When I was just starting to save and invest money, I read The Boglehead’s Guide To Investing. It’s the Vanguard approach - continuously invest in index funds with low fees, and over time your wealth will reliably grow just as much, if not more, than anyone else’s.

I was also reading multiple books on heuristics and biases: the way human minds predictably err from logically or mathematically ideal reasoning.

A tidbit I picked up - I can’t remember where, or even how accurate it was - was that about a quarter of investors would beat the market every year, but that there was no correlation between these investors year to year.

In other words, it was possible for your money to beat the market (achieve above-index fund returns). Just not to do so reliably, over years and years.

(People have done this in the past. Warren Buffet is the name that comes to mind. But the explanation for being able to do this is that Warren Buffet is not beating the market; he’s not smarter than hundreds of thousands of people and computers all competing against each other. He’s doing something else, which in his case is something like ‘evaluating companies on an individual basis for value based on his understanding of both the company and value’. Or something like that; I won’t claim to understand it.)

As I read the literature, the same lesson was repeated over and over: no matter how smart you think you are, you are not smarter than everyone else combined. The market cannot be reliably beaten by an ordinary investor. If you’re not going to be a quantitative analyst and put your own time and blood and sweat into investing, don’t try to get smart.

Just pick an index with a low fee, and ride that ticker all the way up.

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There are other approaches, of course.

But at the time I was making these decisions, thinking about money made me really anxious, so I needed a strategy that involved the minimum amount of thinking about money possible.

Index funds it was.

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I’m a part of the rationalist community. I don’t expect anyone outside of it to know what that means - I’ve had rather comical interactions trying to explain it to others - but one small piece of what it means is that I try to correct for the most glaring errors my brain makes.

The errors I’m able to correct, anyway.

There is a pattern of thought which goes thusly:

Most people are dumb. I am smart. I should be able to do better than most people at this.

Or, the more elemental form of the pattern:

Other people are the rule. I am the exception. If I try, I can get exceptional results.

Being the exception, not the rule, is the heart of almost all narrative fiction, especially fantasy and science fiction. It’s an easy story to tell yourself, especially when you’re a smart kid growing up.

Other people are the rule. I am the exception.

It’s a tempting thought.

Seductive, almost.

It’s also usually wrong.

Most people are the rule. That’s why it’s the rule. Unless you’ve got a compelling reason (and strong evidence) to believe that you’re not the rule, basic probability indicates that you are most likely the rule.

And the rule of the market - not without its exceptions, but the rule nonetheless - is that you don’t beat the market.

I decided that when it came to money, I was the rule, not the exception.

And the rule doesn’t beat the market.

The rule doesn’t get windfalls.

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I don’t buy lottery tickets.

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A strategy can’t be evaluated on its own. It needs counterfactuals to be compared against.

What if I’d done this? What if I’d done that? Zigged instead of zagged? Juked instead of ducked? Attacked instead of defended?

A coherent financial strategy, that I could have feasibly implemented, that would have resulted in me participating in one of those windfalls - well, I can think of one now - maybe, sort of - but could I have thought of it then?

I want to say yes. It feels like I could have.

And maybe, in a perfect world, I would have.

But in this world?

I don’t think so.

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It’s interesting to note that I’d be better off emotionally if a) these windfalls had never happened, or b) I’d never become aware of them.

Events happened in the world that had nothing to do with me, that never touched me or harmed me or affected me, and I’m made worse off by the fact that they did.

Sometimes missing out on a gain feels like a loss, despite nothing having been lost.

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I recently spoke to a friend that did participate in one of those windfalls.

He made quite a lot of money from it.

I was envious - not that I wanted him not to have made that money, but I certainly wished that I had as well.

I don’t know what the difference was between us - why he had participated and I had not. Was it luck? Skill? Risk tolerance?

Was there something wrong with me, that I had let the opportunity pass me by?

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Plenty of people never bought Apple when it was cheap. Same for Tesla, Microsoft, Netflix, and so on.

There have probably been hundreds of get-rich-quick opportunities in the last fifty years, and the overwhelming majority of humanity didn’t participate in any of them.

At least I’m in good company.

I guess when it comes to windfalls I was right: I am the rule, after all.