During college, I spent around 2,000 hours playing DOTA 2.
If you’re unfamiliar with the game… there’s no concise way to explain it. Maybe go watch the finals of the last major competition to get an idea.
The gist is that it’s one of the most complex multiplayer games online, and is one of the biggest competitive esports in the world. Developing even a basic competency in the game requires knowing the ins and outs of 115 different characters. Compare that to the 6 in chess, or the 1 in FortNite.
DOTA 2 was always uniquely addicting to me. The community around it and having friends to play with was part of that obsession, but a bigger part was the way the game challenges you.
In DOTA, you have an “MMR,” a “matchmaking rating” that determines who you’re paired with and against. It’s a rough way to quantify your skill relative to everyone else playing DOTA so that you’re always in a well balanced game.
Because of how robust their MMR system has gotten, you’ll rarely play a game where you completely stomp the other team or get completely stomped. Almost every game is an intense, focused, test of your abilities, where you can only win by being a bit better than you were the day before.
Compare that to any game where you choose a difficulty level (Easy, Normal Hard, etc.). A game with fixed difficulties like this will almost always be too easy or too hard since the game isn’t designed to measure your skill level and adjust accordingly. Not only will this make you eventually get bored or frustrated, but it will hinder your learning. If you aren’t being constantly challenged just a little bit, it’s hard to improve your abilities and stay engaged.
As Anders Ericsson puts it in Peak:
“If you reach a skill level that feels “satisfactory” to you, you stop improving, and even get worse with time… We only learn until we feel like we’ve hit a “good enough” point. As soon as we feel like we’re good enough (subconsciously or consciously) we stop improving, even with continued repetition.”
This is where DOTA and games with similar MMR systems like Starcraft 2 succeed: they force you into constant light discomfort to push you to keep improving. Each game is never too easy or too hard, and most of the time when you lose you can see how you almost won. They manufacture flow states.
Eventually I got bored of DOTA, right around the time I got interested in entrepreneurship.
I don’t think that’s a coincidence: school was incredibly boring, and DOTA provided more motivating challenge. But entrepreneurship provided its own set of interesting, motivating challenges, and that allowed it to displace the DOTA habit.
I suspect a significant portion of our work satisfaction and professional growth comes from our ability to manufacture just the right amount of challenge. A typical corporate job is unsatisfying and limits your growth because you have little control over the challenge level: you’re either overwhelmed and miserable, or under stimulated and bored.
To be fair, entrepreneurship can also be on either end of that spectrum. Usually it’s overwhelming for a while until things start working, but then it can quickly become under stimulating. Luckily, because of the fast paced nature of growing a business, that complacent state usually doesn’t last for long, and some new challenge will pop up to suck you back in.
If the business hits a challenge that’s too hard, it’ll die. If it’s never challenged, it’ll lose to competitors that do seek out those challenges. That’s part of why moats are so attractive to investors: they’re big challenges a business has conquered that will create a barrier between it and competitors.
Individuals are no different. I don’t think it’s unfair to say that the people who accomplish the most are the ones who keep themselves at the right difficulty level. The ones who succeed at continually push themselves in meaningful ways that keep them engaged and learning.
The challenge is figuring out how to do that for yourself.
The best way to have a sense for when you need to up the difficulty is to pay attention to “ease signals,” signs that you might need to up the difficulty to keep growing.
The biggest one to me has always been boredom or laziness. If I find I’m spending a lot of time on reddit, playing video games, sleeping in, I’ve probably let my life get too easy.
I’d argue that depression is a big one for some people. If your life has no exiting challenge in it and you don’t feel like you’re growing, it’s easy to end up in a depressed state.
Validation seeking could be one as well. If you notice you’re going out of your way more for validation, whether that’s Tinder hookups, Facebook likes, party invitations, you might not be getting as much sense of self-worth from your work as you’d like.
Playing hours of video games, posting thirst traps on Instagram, partying multiple nights a week, pickup artistry, are all manifestations of lacking a meaningful challenge in your life. If what you do doesn’t make you feel excited, you’ll seek out an easier but unfulfilling form of validation from virtual worlds, intoxicants, and sexual attention.
But if we can recognize our tendency towards ease, and preemptively intervene to keep the difficulty at the right level, we can sustain a healthy amount of professional and personal growth without being tempted by the vices that want to fill its gaps.
The challenge, then, is how to create that difficulty.
One underappreciated benefit of living in a high cost of living area is that it forces you into this challenged growth state.
When I was living in Buenos Aires, I was making enough passive income to cover my expenses plus savings, so I didn’t feel pressured to push myself. The steaks and wine were great, but I had little professional or personal growth in that time.
Fast forward to living in New York City, and it was suddenly a very different ballgame. My cost of living was about 3x higher, and there was no way I was going to be able to live comfortably on 2-3k a month.
I knew I needed to start doing something else to make money, so I started Growth Machine, and a year and a half later, it’s done better than I could have imagined.
I suspect that part of why we see so much growth and innovation in places like SF and NYC is the high cost of living. It’s hard to be complacent and when you’re paying $3,000 a month for a closet. Survivorship bias is definitely part of it too, but you can’t discount the kind of energy and drive living under that type of pressure provides.
Luckily, you don’t need to live in a high COL area to take advantage of this. You can manufacture financial pressure by creatively hiding your money from yourself.
The easiest way to do that is your 401k and IRA investments since you can’t touch those for quite a while. Other ways would be having a savings account that’s removed from your checking account (e.g. checking through Chase and saving with Citizens), investing in long term illiquid assets (startups, real estate), or working through a single owner LLC and pretending the company’s money isn’t your money (weird hack, but it works).
Also, I know debt is scary, but if you raise money from investors, sign a long term contract, or run up some credit cards to get a business started, that’s going to be a strong motivator.
Beyond cost of living motivators, a few strategies come to mind for upping the difficulty:
Personal commitments: Getting a dog, having a kid, remodeling a house. I’m not saying pop out a baby just so you can challenge yourself, but it will have that effect.
Projects: Everyone should have some kind of creative side project they can put their extra energy towards, especially when you don’t need to direct all of that energy towards your main focus. Not only does it create drive personal and professional growth, it might lead to new ideas and lessons for your main work.
Scale: Building on the side project idea, any efforts to scale something you’re doing for fun will naturally lead to increasing the difficulty, especially as you hire people to help with it.
New domains: Branching out into an area you’re tangential to but unfamiliar with is a great way to increase the difficulty. For me over the last few years that’s been freelancing -> consulting -> agency -> ecommerce -> physical retail. Each area is related to the one before it, but also new in some interesting and challenging way.
Even if you don’t see a difficulty lever here you can pull in your life, I suspect you could come up with a few if you thought about it. We spend so much time thinking about how we can make our lives better or easier, it’s fun to consider how we might make it more challenging from time to time.
Whatever levers you decide to pull, the best framework for thinking about this progressive difficulty is as an Infinite Game, from Finite and Infinite Games by James Carse:
““There are at least two kinds of games. One could be called finite, the other infinite. A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.” (emphasis mine)
Our goal shouldn’t be to defeat the challenges we’re dealing with, rather to progress from those challenges to bigger, more meaningful ones. If we expect we’ll be satisfied and happy once we hit a certain goal we’ll almost certainly be wrong, so we should instead always look for new ways to push forward and continue growing.
To borrow another line from Carse:
“Work is not an infinite player’s way of passing time, but of engendering possibility. Work is a way of moving towards a future which itself has a future.”
Progressively increasing the difficulty is how you ensure you’re always moving towards a future which itself has a future. It’s how you avoid getting bored and complacent, and how you maintain an exciting, motivating level of growth.
It’s not easy to do, and it won’t happen without a deliberate effort. So it’s worth occasionally asking yourself:
"How can I make this more challenging... in a way that won't destroy me?"