Paul Graham’s recent essay “Lesson to Unlearn” helped articulate something I’ve been thinking about for the past several years. He says:

There are certainly big chunks of the world where the way to win is to hack the test.

Graham talks about “bad tests” – ones that incentivize people to re-orient their entire attention towards doing well on the test as the primary goal.

In a guest post here on Boundless, Ranjit shared how he stumbled upon the easy-to-follow “test” of breaking into BigLaw:

The great thing about choosing a career like law is that the steps are laid out for you. Life’s existential fears are traded for certainty. Even the uncertainty of winning a training contract was off-set by how formulaic a process it was to land one: attend work experience, attend a summer scheme, talk-up made up extra-curricular activities etc. 

Graham argues that many people follow these paths because they accept “this is the way things work.”

I suspect many people implicitly assume that working in a field with bad tests is the price of making lots of money. But that, I can tell you, is false. It used to be true. In the mid-twentieth century, when the economy was composed of oligopolies, the only way to the top was by playing their game. But it’s not true now.

This certainly resonates with my own perspective as I graduated college and early in my career. It wasn’t until about 2014 when I started to see new possibilities emerge.

📝 You Still Need To Know How To Hack Tests, But Its Not The Only Game

Most college students ask me one type of question:

“What can I do to get accepted by ___________?”

They want to know the answers to the test.

I’m no better than any of these people and this is why I’m interested in writing about it. For the first ten years of my career, I became highly skilled at determining the rules to “bad tests,” and molding myself to gain entry to jobs and universities.

Graham describes my former worldview well:

You might actually like to win by hacking bad tests. Presumably some people do. But I bet most people who find themselves doing this kind of work don’t like it. They just take it for granted that this is how the world works, unless you want to drop out and be some kind of hippie artisan.

I kept playing the game, but increasingly grew to be frustrated with the fact that there was no end to the game. Playing the game seemed to matter more than what you actually did and especially so the higher you got within a company.

When I “dropped out” I was driven by a hunch that there might be more ways to play the “game of work” than ever before.

Turns out I was on to something..

In the first year I discovered that starting from scratch and really focusing on trying to do great work was pretty hard. I felt pretty insecure about what I was doing and found that I was pretty bad at a number of skills that I never really had to test with “skin in the game”: negotiation, end-to-end consulting projects, coaching, listening, business development, design, writing, web development and so on.

Over time, I started to gain a little confidence that there was some payoff in continuing to learn and get better at a number of these things.

I’ve become optimistic because of this and think that there are more ways than ever to make a living through work and to find ways to be rewarded for trying to do great work. This sentiment is shared by Graham:

The more I think about this question, the more optimistic I get. This seems one of those situations where we don’t realize how much something was holding us back until it’s eliminated. And I can foresee the whole bogus edifice crumbling. Imagine what happens as more and more people start to ask themselves if they want to win by hacking bad tests, and decide that they don’t. The kinds of work where you win by hacking bad tests will be starved of talent, and the kinds where you win by doing good work will see an influx of the most ambitious people. And as hacking bad tests shrinks in importance, education will evolve to stop training us to do it. Imagine what the world could look like if that happened.

Don’t Become The Game

I always give one piece of advice to the students I talk to:

“understand the game…don’t become the game”

In my last job I worked with companies to help them assess internal candidates for CEO succession. In one company the eventual successor told us in an interview why he should be the one they pick. He laid out his twenty year career path of working in every function, business unit and region of the company. Exactly the impossible mix of experience that most companies look for when trying to promote someone to CEO.

Was he lucky or did he hack the test? Turns out this was all by design. Early in his career he told us that he “decided” he wanted to be CEO and set out to make it happen.

He became the game.

The reason I’m concerned about this is I see more and more people doing the same thing as the CEO. They come up with a certain goal, identify people who have what they want and then try to reverse engineer how those people got there.

The most striking example of this is when I hear many of my friends starting to talk about college already even though their kids haven’t even left the home. They seem to be embracing beliefs I didn’t really know existed until I entered elite circles myself:

there’s the implicit belief that a premier prekindergarten program guarantees an early leg up in a nearly 14-year battle to gain admission to the country’s most competitive colleges.

Growing up I was lucky to not really have a lot of pressure on what I was meant to do when I grew up. I didn’t even think too deeply about college until I was a junior in high school. Even then I only applied to one school.

I started teaching myself the rules of the game when I was in college trying to break into strategy consulting. Perhaps this enabled me to abandon the game in shifting to my current path. It never really felt natural and I suspect for many of you, you hate how much you have to play the game.

Unlearning this mode of being was hard, but also worth it. Even though I haven’t fully unlocked “permanently successful solopreneur mode” yet, I feel more alive with learning, curiosity and optimism than ever before and seem to be playing a game that I can live with.



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