Virtually every single thing you have ever been told about luck is wrong. Let me show you what you’ve been missing.

What Is Luck, Really? (II)

Five years ago I wrote an article titled What the Definition of Luck Really Is. It’s exceedingly rare for me to agree on something I said so long ago, but this one is different. I’ve really become obsessed with the idea that everyone got luck wrong, and even back when I was writing in that little corner of the university library I was thinking maybe luck isn’t something that happens to you, but rather you happen to it.

Five years later, and the only difference is that I’ve tried that theory out.

In 2023 I quit my full-time job to become a human guinea pig in trying to “make it” — in other words, generate a full independent income for myself without needing to work for someone else. Two things have happened in the time since then. The first is that I, to be truthful, haven’t made it. But the second — and more surprising — realization is that this all is a lot easier than I thought it would be.

And at this point I think I see the light at the end of the tunnel.

The rest of this blog post is dedicated to discussing what exactly I mean by “easier than I thought” and “seeing the light”. But before we get into that, I want to give a reminder as to what I see as the definition of luck.

When someone says “to be successful in starting a business requires luck”, what they probably mean is “to be successful in starting a business requires certain probabilities that may or may not be in your control”. Of course, that’s a bit of a word wall, so I understand the abbreviation — but there’s a few key nuances in that second statement we need to check.

The first is defining what those probabilities actually are. In most cases of the usage of luck, it can be summed up as “the probability you find someone who is willing to spend money to help you live your life”. If you are an artist, then your luck is people finding you who want to give you commissions or buy your merchandise. If you are an entrepreneur, then your luck is people finding you who want to buy your product or pay for your subscription. If you are an athlete, your luck is people finding you who want to sign you onto your sports team. If you want a girlfriend, your luck is… well, perhaps there are ways to pay other than with money. But I digress.

Of course, this is the definition good luck. Bad luck would just be the inverse: it’s the probability you find someone (or something) that is willing to take away your money. The stock market, healthcare bills, a tornado, and sudden death are all things that fall under this description.

Any other part of this conversation would be considered to be skill. An artists has their drawing skill, entrepreneurs their skill in sales, athletes their physical prowess, single men their charisma. But as you can imagine, all these things have a direct impact on luck as we have defined it! People are more willing to buy from an artist if they make good art rather than bad art, but the quality of the art is something that is under the control of the artist — even if the buyers are not.

Now, let me show you something that’s interesting: the more you broaden your definition of success, the better your chances of luck becomes. Look at me: my goal is not to become a rich and successful writer, my goal is to generate a full independent income for myself without needing to work for someone else. I do not mention an occupation or skill, and because of that I open many different avenues where I can utilize my greatest skills and find many different types of luck. This is more or less what’s described in the famous Luck Surface Area article, but I prefer to think of this like a spider web: You are the spider, spindling your set of skills, your offerings, your self-promotion, until eventually you are able to catch some flies (more affectionately known as “customers”).

The Great Filter

The Great Filter (at least, in this context) is the social stigma involved with “going your own way” as opposed to sticking with the status quo and holding “a real job”. The Great Filter is ever present, both among liberals (if your goal is to be an entrepreneur) and conservatives (if your goal is to be an artist). It often comes in the forms of “you are never going to make it” or “why haven’t you made any money the past two weeks?” or “can’t you just do something more stable?”.

But the worst part about this filter, at least in my opinion, is that it suffers from the same bias as the stock market: it uses science to analyze something that is purely psychological. If you dive deeper into why people believe in the Great Filter, they will almost always say that it is statistically impossible to be successful. That only 1% of people have all the money, and the rest of us have none. That success in these fields is an on/off switch: you either have it, or you don’t. You have to be so incredibly lucky because the chances are so low, that you might as well not try at all.

I used to hate this filter, when I was on the other side of it. But when you’re in the game, the filter changes in a very interesting way. It doesn’t get more positive — it gets more transparent. I now have people telling me every week that I’m “dirt broke” and “chasing an impossible dream” when I still have six figures in the bank and break even almost every month. Before the Great Filter made me worried none of us were going to make it. Now, it has assured me that we are all will.

What the hell happened?

How Pareto Ruined Statistics

The most common statistical rule when citing the Great Filter is the Pareto distribution. In its most general terms, it is a distribution in which 1%-20% matters to the context of what is getting measured, and the other 99%-80% don’t. For example, in the shape of total book sales, 1% of books fill in almost all of the total, whereas 99% of books fill in the scraps.

To be clear, the Pareto distribution is real. If you look at any risky venture — book sales, successful startups, trading results — they always really do follow this rule.

But there’s a lot of things the Pareto distribution doesn’t tell us. As I said, this statistic is used to give scientific credence to something that is not driven by science, but by people. A market in which goods with no real predefined value are bought by some humans and sold to others. Sound familiar?

So, as we begin to look deeper into these distributions, some cracks start to appear. The first — and most obvious — is where this data is coming from.

Tell me, which one of these sounds more like a failure to you: 1) Someone who writes a new book every six months, working day in and day out for ten years, getting zero sales on every book and eventually going bankrupt, or 2) Someone who writes one fantasy novel based on a dream they had, publishes it to Kindle, then realizes maybe this writing thing is too hard and goes back to his desk job.

Subject 1 is the depressing, fearful reality brought to us by the Great Filter. Fortunately, it is not actually a reality: the wide majority of the Pareto’s 99% is driven by Subject 2.

If you’re grabbing the sales of every book released on Kindle, I’m sure there’s going to be some sob stories in there. But the wide majority of it are going to be these one-off cases or, even worse, content farms that don’t really care if they spit out 1,000 books a year with zero sales. These are tainters of the data, and very rarely are they selectively removed from the statistics.

There’s another issue, too. We’re look at book sales per book. If we’re trying to uncover success rates, this doesn’t really tell us anything. One person can get fabulously wealthy off one blockbuster hit after writing twelve duds, or off a few paltry titles that add up to a nice income. The whole strategy of content farms relies on this: they’ve realized if they throw enough books at the book-fire, they’ll still hit their profit goals. And yet you wouldn’t be able to tell that by looking at the graph.

Now, remember what I said about Subject 1 — the ten year case? Well as it would turn out, something funny happens to this Pareto distribution once you get rid of these filler cases and focus on the real workers: people who stay disciplined and consistent for ten years in a given domain. For the wide majority of them, their first book is a dud. Their second book also a dud. Same with the third book. But then, they just keep going: the fourth, the fifth, the sixth, all without a care. All of a sudden, one book pops off. And then another, and another. Fans, who find these individual cases, begin to scour back to books one through three. And now all of a sudden a certainly doomed case is an example of the 1% who make it.

Here’s something that will flip your whole theory on your head: if you take any Pareto distribution — startups, books, musicians, financial traders — and filter it so that it only includes those who have been in the game at least 10 years, the Pareto distribution converts into a Normal distribution. Every single time, without fail.

Welcome to the 10 Year Rule.

“The Real World Doesn’t Operate On Numbers”

Beethoven and Mozart are considered to be the world’s most successful composers. But what few people know is that they’re also the most prolific composers. You can look in other places and find the same: the ones who write the most books are the most successful authors, the ones who start the most startups are the most successful entrepreneurs, etc. etc.

Risk-seeking fields should not be considered dangerous because of their amount of failures, but rather that a large amount of failure is part of the process. It is merely given the appearance of danger based on the failures required.

I once read an anecdote where a successful equity trader was quoted saying “The real world doesn’t operate on numbers, it operates on bullshit.” I think the context was different, but you can easily use it here. In order to be successful in this world, you simply need to deal with a lot of bullshit until things work in your favor.

Besides… what is successful?

American game developer Scott Cawthon worked in the industry for 20 years as a solo developer until he eventually released the commercial megahit Five Nights at Freddy’s, propelling him to the status of multi-millionaire. But in the 20 years before, Cawthon was still working independently! With the help of freelance programming jobs and content farm mobile games, he had time to work on his passions. And while it certainly wasn’t bringing in riches, it was bringing in sustenance.

This “sustenance” segment of risktakers is something that’s not widely talked about. Most people assume that 99% of entrepreneurs and artists make no money at all and live out on the streets, and 1% make billions. The truth — further disproving the Pareto myth — is that the wide majority of these creators live anywhere between right below minimum wage or taking in a rather mild salary. The idea of “working until homelessness” is a myth akin to trying to kill yourself by holding your breath. Life finds a way.

However, here’s where the hard part of this conversation is going to come into play. There will be those among you who say that this isn’t what success looks like. You might be living “the independent life”, but at what cost? Beans and rice for every meal? Skipping out on holidays because you can’t afford them? Living without health insurance, then freaking out whenever you get a mild cough thinking it might be the sign of something worse?

Well, to tell you the truth, this is still a game you play. In order for it to work, your full heart has to be in it. After all…

I Never Said It’d Be Easy

The point of this post is to tell you that you will be lucky. That, if you elect to play the game, things will be easier than you think because you do indeed have luck on your side.

But it is not easy. It is just easier than impossibility.

The Great Filter exists for a reason. Ten years of doing something with no reward is a mighty long time. It is something that most people will not have the heart, soul, care, or willpower to do. If you survive this bootcamp, you will make it. But you’ll make it when you get through West Point, and it still has one hell of a dropout rate.

Most of you will end up becoming a one-off case, another failure in the Pareto statistic. You will make one thing, be disappointed by the reaction, and never work on anything again. But those who are ready to soldier up, to brave your way through the Great Filter, to deal with bullshit for ten years — we are all most certainly going to make it.

To end it off, here are some of my tips for the soldiers:

• You need ironclad discipline. The idea of doing something every week, every day, for ten years — especially something you are not forced to do by an employer — is near inconceivable to most people. Even I admit that, in my relatively small six year journey, I’ve stopped and started again. I’ve taken up projects, put them on hiatus for 8 months, and came back to them only to work on them for a week or so. That sort of behavior isn’t going to get you anywhere on this path.
• Part of the problem with discipline is having too many hobbies. If you have one deadline you have to hit every week for the next ten years, it’ll get boring but it will be doable. But if you try to have ten different deadlines every week, you’ll never end up getting anything done. You want to stretch yourself out enough that you never get bored and you maximize your spider web, but never to the point where you feel completely burnt out.
• One way to help with discipline is by increasing your number of “reps”, or turning your releases into more sizable chunks. For example, instead of making an album — which could take six months — you instead focus on making a single every two weeks, and publishing it right then and there. Instead of a book, turn the chapters into posts on a blog. Instead of big product launches, iterate on features and share them on Twitter. Etc., etc.
• You still have to be smart about all this. If you aren’t smart, you won’t make it no matter how long you work. Fortunately for you, being smart’s not that hard. It simply involves learning what works and what doesn’t, then doing more of what works, and less of what doesn’t. Sometimes people will be trapped into watching the latest hustler scam video, thinking that they really need to make a TikTok content farm, “because look how much money that one guy made!”. Beyond breaking your concentration from what matters, it also probably isn’t worth doing if you’re getting no clicks after a month of content. But if you see the momentum building — however small — it’s always something you want to focus on.
• Finally, you are in a risky field — learn risk management! My trader friends know the power of this: cap your downside, and unlock your upside. Make yourself a budget. Create an algorithm or check sheet for you to follow that tells you what to do if you ever hit a dangerous net worth threshold. The more concrete it is, the better. You will find that any smartly managed risky venture is punctuated by months of small downsides, then a single day of massive upside. With enough compounding, the upsides begin to pay for themselves.

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