13 min read

You don't take enough risks to be lucky

How I think about long-tailed outcomes

I quit my job a month ago, which will probably end up among the best turning points of my career. To be clear, there was nothing wrong with that job, the alternative is just that much better. My social and professional networks have grown dramatically. I have the most intellectual freedom I’ve ever had, letting me discover and work on [redacted], [redacted], and [redacted]. Above all, the degree of agency and ownership of my life and success is intoxicating. I might sober up eventually, but for now it’s hard to imagine wanting to work a regular 9-5 any time soon.

There might be some collective wisdom on this. I honestly expected a lot more concern and muted skepticism whenever I revealed that I’d quit my job. What I received instead was congratulations, excitement, and curiosity. My guess is that good things seem to happen when someone voluntarily makes a big life decision. Maybe they have an amazing opportunity waiting for them, maybe leaving their comfort zone creates amazing opportunities. Maybe I’m just surrounded by relatively fortunate young people without enough financial commitments to make unemployment truly scary.

Anyways. The point of this isn’t to convince you to quit your job. This was a fairly lucky outcome, but I didn’t plan for that, and the point isn’t to brag about it either. I’ve had a lot of lucky outcomes in my life, and the point of this is to share how I made that happen and how you can be luckier, too.

What do you need to be lucky?

Luck is random, but it’s not purely random. If we think of being lucky as having net positive impact from random chance in your life, then we can be skillful by selecting more opportunities where the odds are stacked in our favor. This is hard because the odds are usually too fuzzy to compute.

This implies a few prerequisites for practicing luck as a skill. First and foremost, you must have an appropriate amount of belief that you can have an impact on the seemingly random outcomes in your life. Our belief in this is heavily conditioned on how lucky we’ve been, and we tend to over attribute skill when good things happen and over attribute random chance when bad things happen. As a result, there are people for whom this feels obvious and people for whom this feels impossible, but both parties are off the mark. Underconfidence means you never take enough shots on goal, but overconfidence means you’ll bite off more than you can chew, and you’ll really be gambling more than practicing luck as a skill.

You must also have an appetite and tolerance for risk. The goal here is to select more opportunities with odds stacked in your favor, but that still means taking a lot of opportunities where odds are involved. That means you will still lose a lot of bets. Humans are naturally risk-averse, and it will feel bad to lose bets. Dealing with this over time requires a high tolerance for failure, and you must have tolerance both in your mental game and in having sufficient resources to absorb the negative outcomes. Resources here can mean things like time, energy, money, social status, etc, and having more resources makes the mental game easier. Quitting my job was made much easier by knowing how long my savings could last and that I was fortunate to have a valuable skill set.

It’s a rigged game

Fortune is not evenly distributed. Some people are born richer, some with more social status, some are more neurotypical, some more attractive, and on and on. People with more of these resources have access to more opportunities, and as a result, access to more opportunities with favorable odds. It is easier to afford the necessary risk of these opportunities if you have more resources. Although this post is not about the distribution of these resources, make no mistake: this is the truth and this is not fair.

That being said, you can make a meaningful impact on your future luck. Whatever your starting point is, you can beat a majority of people who don’t try, and most people don’t try. It also gets easier over time; luck begets luck. Quitting my job was easier because of my savings and skill set, but the size of my nest egg mostly came from a couple of unique bets that turned out well. I chose my career from the overlap of things I like and things that pay well, which increased my access to good opportunities. Those in turn came from earlier, smaller things. Wherever you start, your luck can gradually snowball and change your life.

A closely related concept is playing to your outs, and nearly every life situation has outs, however improbable. These might only serve to make a terrible situation into a slightly less bad one, but they exist for those with the desire to find them. I sincerely hope you are not in such a terrible situation, but if you are, you probably aren’t an exception. As harsh as that sounds, it’s actually a good thing. The upshot is that you can make a meaningful impact on your future luck. The game is rigged, and the game is hard. We’re stuck playing it anyway, so let’s play with our eyes open.

Luck is making chances to dig for outliers

The first hard thing about being lucky is realizing that you can just do things. This is like the extreme version of noticing you can just choose to have cake for dinner. You have ownership over your life, and you are allowed to do more things than you realize to make it better.

The second hard thing is noticing all the places in your life where you might want to do something. When I say all, I really mean all. Noticing that you can quit your job isn’t hard. Neither is noticing that you can go on a backpacking trip through Europe, that you can have kids, that you can exercise more, or that you can move to that city you’ve always dreamed of living in. People talk about these things all the time. They’re worth thinking about, but far from the only things worth thinking about. Sometimes exploring the full space of Bets You Can Make looks like staring into the abyss. Sometimes it looks like ordering a dish you’ve never tried before that sounds kind of weird.

The next step is evaluation; not all of these bets are good bets to take. I’m going to focus on a particular type of bet, which I think is fortunately both the easiest to talk about and the most useful. That class is one where there’s potential for huge outliers in outcomes. This is what that looks like as a graph:

This type of distribution is called long-tailed, heavy-tailed, or right skewed. Line 1 shows roughly where the median outcome is. If you only take a few of these long-tailed bets, then you’re likely to only end up with approximately median outcomes, and your luck will feel average. Line 2 shows roughly where the mean outcome is. The key here is that the downside outcomes are minimal and bounded, and the upside outcomes are massive and practically unbounded. If you take enough bets with this distribution of outcomes, then you’ll eventually pick up enough outliers (line 3) to bring your net outcome well above the median. This is also a theory for how diversified portfolios manage to beat treasury returns. Most individual stocks end up with lower return than treasuries, but they’re incredibly long-tailed, and it’s the few outliers that cause a diversified portfolio to outperform treasuries.

Ben Kuhn has a great post on systematically searching for outliers within specific domains, such as job selection, blog post writing, or startup investing. These tasks have common features:

  • You can keep resampling from the distribution by taking new jobs, writing new posts, or investing in more startups
  • It’s hard to tell how good the outlier outcomes can actually be, especially with low sample size
  • Scoring a few outliers covers the cost of searching and then some (and usually a lot more than some)

One of the key takeaways is that finding success in those domains is largely a function of how well you can repeatedly sample from their outcome distribution.

My addition to this process is that you don’t have to compartmentalize it to each specific domain. Suppose you have 1 domain with a specific outcome distribution and 100 other domains that all happen to have a similar outcome distribution. Assuming you’re equally happy to get outliers in any of these domains, you can get as many expected outliers by sampling from the first, single domain 100 times, or by sampling from each of the 100 unique domains once each. In either case, you get to the same number of attempts at scoring outliers.

Long-tailed results also typically take a long time to be realized. You don’t get immediate feedback on whether the job you picked or the partner(s) you’re with is an outlier. There’s a serial nature to these selection tasks that limits the number of shots you have in your lifespan. If it takes a couple of years to figure out if the job you’re at is really exceptional, then focusing solely on resampling new jobs might leave you with only a couple dozen shots on goal in your entire life (and the longer it takes to find an outlier, the less you can reap the benefits). You can roughly double your shots on goal to find (any) outliers in life if you parallelize the process of resampling your job with resampling your romantic partner.

Why stop at two parallel processes? There are more unique domains than you realize that have long-tailed outcomes and that you can parallelize your sampling from all these domains.

Unfortunately, this is where the whole thing gets much harder. The biggest source of parallelization is going to be from decisions that are very specific to your life path and that you might only get to make a few times in your life. You might miss them, and if you see them, you might misevaluate them. There are a lot of these types of decisions, and not all of them have this long-tailed outcome distribution. Here is a quick, non-exhaustive list of things you might not get to do very often and which have varying degrees of difficulty, impact, and endorsement.

  • Picking an advisor in grad school
  • Getting married
  • Having an expensive wedding
  • Getting divorced
  • Having kids or not
  • The number of kids to have
  • Adopting a kid
  • Adopting a pet
  • Choosing a career (especially a high-commitment one, like being a doctor)
  • Trade on a potential Black Swan event
  • Committing major financial crimes
  • Buying a house
  • Emigrating to a new country
  • Donating a kidney
  • Undergoing gender-affirming care
  • Following a particular religion
  • Taking a particularly unique job abroad
  • Whistleblowing

These are still things that are common or high profile enough that anyone can think of them, but access to opportunities is highly path dependent.

Credit: Wait but Why?

Your full list of opportunities will look very different from mine, and it will be much longer than the list above. Your list will be unique and constantly changing, because it depends on your skills, resources, connections, and the state of the world around you. To be luckier, you must be able to frequently and accurately update your list and pick which ones to take the leap on (please don't pick major financial crimes).

QR codes generated by ControlNet

A recent example that comes to mind are these beautiful, functional(!) QR codes generated by ControlNet. I’m familiar with Stable Diffusion and other generative AI models, but my brain contains basically zero knowledge about QR codes (it turns out QR codes are quite malleable). I wouldn’t have considered this to be on my personal list of opportunities, but for this person, it was and they took it. This wasn’t just a once-in-your-lifetime opportunity, this was once-in-anyone’s-lifetime. Now they get to be “that person that made super cool QR codes” forever, and no one else does. Depending on what you’re optimizing for (visibility, career opportunities, internet fame), this could be a fantastic outlier outcome for a speculative project.

Going for those one-off chances doesn’t lend itself to a clean framework of resampling on the same decision, but it does expose you to many more potential outliers over a lifetime. You can get lucky in a particular domain by understanding how to search for outliers in that domain and by repeatedly sampling from that domain. This is good, but this still limits your shots on goal. You also might not find a life-changing outlier until late in life.

You can get even luckier, and sooner in life, by being able to accurately identify all the domains of long-tailed decisions that are accessible to you and learning to search for these outliers everywhere. Even if some of them are once-in-a-lifetime opportunities, once-in-a-lifetime opportunities abound.

“But X is already pretty good”

At the job that I left, I previously held the belief that it was an exceptionally good place to work. My basis for believing this was that many of my coworkers frequently commented on it being the best place they’ve ever worked at. Surely if so many people think so, there must be some truth to it being exceptional?

I still believe it was a great place to work, but (as Ben Kuhn also discusses in his post) there’s a difference between being at the 90th percentile (great) and being at the 99.9th percentile (exceptional). If you’re at a 90th percentile company and most of your colleagues have worked at around 5 places in total, there’s a 65.6% chance that your 90th percentile company is better than all of the previous 4 places they’ve been. So being at a 90th percentile company might look like two thirds of your coworkers truthfully being able to say it’s the best job they’ve ever had, even though 1 in 10 places are better.

Truly strong evidence of an exceptional outcome looks stronger than two thirds of people with something comparable saying it’s the best outcome they’ve ever had. Evidence of an exceptional outcome looks more like zero people around you with something comparable. Without this kind of evidence, chances are that a given situation in your life is closer to a median outcome than you think it is. If so, the risk for rolling the dice again is also lower than you think it is. In general, we bias away from change, but we should try to embrace it to become lucky. In 2020, a study asked 20,000 people to make some difficult decision on their mind with a coin flip:

For important decisions (e.g. quitting a job or ending a relationship), individuals who are told by the coin toss to make a change are more likely to make a change, more satisfied with their decisions, and happier six months later than those whose coin toss instructed maintaining the status quo.

(n.b. If you're a former coworker, don't take this as advice or judgement. I haven't even worked at 5 places yet!)

What you can do to get luckier

The basic feedback loop

Network more. Every new person that you develop a connection with, either socially or professionally, can be a long-tailed outcome. That might sound a little sociopathic, but the quality of our relationships predict a lot of our life happiness, so we should be more intentional in creating chances for outliers. Most people will be acquaintances, but some can be lifelong friends, romantic partners, and/or collaborators. Furthermore, a rich and healthy network might also spot long-tailed opportunities that are uniquely suited for you and bring them to you. Noticing good bets is easier when you have more bets to choose from, and having a strong network is much faster than searching alone (pay this forward!).

Be curious, too. It costs less energy to spend time learning about things that excite you. Doing great work often looks like following your curiosity to places where people haven't tread before. This can mean going deeper than anyone else has, but it can also mean going broad enough that you find a unique combination of knowledge, as with the earlier QR code art.

In the long term, it’s crucial to develop a strong probabilistic mindset and intuition, which makes it easier to reason about whether a decision is potentially long-tailed or not. This also helps avoid certain types of opportunities, such as the lottery, which is arguably long-tailed due to massive outliers, but not actually worth it. Finally, this helps identify downside risk, so that you can avoid making a decision that leads to a complete blow up. As you’re exposed to more chances, you’ll develop a better sense of what makes an opportunity good or bad in this framework, including making more accurate assessments for more unique long-tailed decisions that you only get to make once or twice.

There isn’t a lot of general advice that I can offer beyond this. The ideal situation for developing a skill is one where you can do deliberate practice, but this framework can’t be applied to the domain of luck. There are no well-established training methods, and as far as I can tell, no one officially coaches for being lucky. A lot of my personal skill in this domain falls under gut feeling, or tacit knowledge, and I haven’t thought explicitly about this enough to make that gut feeling explicit. If you’ve thought about this and have ideas, please share them. In lieu of a perfectly written guide, here are some things you might start with:

  • Interview occasionally at jobs that sound interesting, even when you aren’t looking for a new job
  • If you’re introverted, get adopted by an extroverted friend
  • Say yes to invitations as a default
  • Do more things where the worst that can happen is nothing
  • Do fewer things that look like sitting at home and watching Netflix (I am guilty of sitting at home and playing video games)
  • Go to random events or activities on Meetup or Eventbrite
  • Start saving up some resources to be ready for opportunities when they come; remember that your resources are resources, and you should spend them (wisely)
  • Don’t do pyramid schemes

Mileage is the best teacher available, so find some risk you can tolerate, and start taking some shots.

This is my first post. It was inspired by this unfinished draft by David R. MacIver and by this post on starting a blog by Ben Kuhn. I recently re-read it for the third or fourth time and finally got off my ass to try my luck with it.

Thank you to those who volunteered to read drafts: AJ, Cyrus, Felix, Ross.

Any feedback is appreciated!