The most important choice you make in your career is which trap you end up in.
I spend an unusual amount of time career planning. For myself, my team, the founders I work with, and individuals I might. Here’s what I found after observing a few hundred lives, including my own:
I don’t have ambitious preferences. The things I enjoy are cheap — music, some people, reading, competitive games, and the cold. I can do almost everything I like for free.
After reading this book on retiring early, I realised that with relatively attainable savings I could retire. My preferences are a lucky fluke.
But I haven’t retired yet, probably won’t anytime soon, and have almost no savings. Like most people I have a remarkable talent for spending whatever I earn.
This is hard to explain. My job doesn’t seem to match my preferences: I’m lazy but have endless work; I get so stressed my eyes twitch; and people rely on me to be stable though I’m naturally emotional. I am far from the people I love.
This is an observation, not a complaint. My job is as good as any I can think of. But, given my preferences, turning up for the day to day feels irrational.
The area under the curve
This feeling of irrationality is shared by many of the founders I work with.
Running a company means enduring a series of painful problems. When you’re the boss, everyone else’s most painful problems trickle up to you. Your day is going from one to another. The burden is enormous.
Usually, your actual, phenomenological experience is not positive. At best, it’s day to day bad, month to month good.
Founders rarely say they don’t like their job — it isn’t compatible with the image you need to present to employees and investors. Everyone is different shades of Elon Musk.
Running a good company is not just difficult, but it’s irreconcilable with other preferences. I know no succeeding founder seriously developing themselves outside their company.
If you plot your experienced happiness over time, the area under the curve will often be negative. Hence the cliche, ‘if I knew what it’d be like, I’d never have started’.
When I left university, most people did one of three things.
Some friends got ‘normal jobs’, which weren’t extremely well paid or traditionally ambitious. These friends explore their preferences outside work and, if they’re lucky, have a job they’re interested in.
Other friends got ‘good jobs’, which paid more and were considered ambitious. They usually weren’t interested in the work itself, except insofar as it made the job prestigious. These jobs have taken up most of their time since — how else could they be ambitious?
A few friends (I studied philosophy, so you know the type) tried to abstain from both normal and good jobs, but have largely caved by now.
I couldn’t have predicted who would do what, except in extreme cases. Early on, most people aren’t that different. My eventually high flying finance friends dressed pretty much the same, went to the same parties, and did the same things as everyone else. Who ‘everyone else’ was wasn’t obvious, because everyone applied for the same jobs anyway.
But, someone had to get the job, so some people did and some people didn’t. This changed our lives forever. For many, this job lottery was a defining, snowballing moment.
I feel the effects every day. I got a good job after university, and hated it. For me, the area under the curve was overwhelmingly negative. The path ahead was clear, but I dreaded taking it and becoming my boss.
So I quit and got what was definitely not a good job. I started working at a (then) tiny non-profit called Entrepreneur First (EF) which had only the co-founders on payroll. Not only was it not a good job, it technically wasn’t even a job — I was unpaid. My Dad inferred I was ‘throwing away my life’. I had followed my philosopher friends to the third way — seemingly doing nothing at all.
This not-even-a-job job turned out to be a good job after all. With luck and effort, EF now has serious (for profit) potential. I’ve got to do things I had no known prior preference, or qualifications, for. I might even make some money out of it — I am at least now being paid — and my friends think I’m ambitious.
The ambition trap
If EF hadn’t been EF, I’m not sure where I’d be now. Accidents happen but, if that one hadn’t, things would have been different.
Like most people, I want to do something important. My ambition is not about anything in particular — it’s opportunistic. I wore the same(ish) clothes, went to the same parties, and liked the same things as my friends, after all. But, for me, this opportunity came along.
And because it did, things are different. I think something very particular:
Don’t blow this opportunity. You have to make it happen.
I’ve reached the point of no return. Forget the area under the curve — the stakes are too high, and I am afraid. Afraid of failure, sure. But more afraid of not capitalising on the opportunity, of missing out, of not taking my chance. Until I saw the opportunity, I couldn’t take it. Now I see it, screw the curve.
So I work my lazy ass off, enjoy every eye twitch, and look after my team. Day to day bad, month to month good. I’m in the ambition trap.
Pick your trap
I see this transformation in the founders I work with at EF.
Most don’t start out different to you or me. Even the best founders mostly start just wanting to do something. They aren’t destined to build a particular company — many of them aren’t, honestly, sure if they want to build a company at all.
They don’t come with an idea worth spending a decade on. They don’t know who they’ll spend a decade with. They don’t know about the area under the curve. They discover it, and then it’s too late to do anything else.
Most good jobs are traps. They increase the stakes until you get to the point of no return. But good jobs are different in different places. Why? Ambition is less specific than its effects make it seem: people go mostly where their environment aims them. The ambitious ones just go the furthest.
If you’re able to go far, think hard about where you’re aimed: the farther you can go the longer you’ll spend getting there.
EF aims you in a very particular direction — to build a company that’s important to you. We help find the idea you can’t forget, the team you can’t let down, the investors who increase your stakes. We aim you at your point of no return. Not everyone gets there. But those who do, get trapped.
If you’re going to get trapped, at least pick a good one. You can’t choose your preferences, but you can choose how to ignore them. In the end, you are not your preferences: the right trap changes who you are and what you can do. The right trap is a wonderful thing.
But not all traps are good. Bad traps get you stuck under a curve you wouldn’t choose again. And they’re easy to end up in: your environment aims you at them. We’re all different, but culture only shows a few ways.
Pick your trap, or someone else will pick it for you.
Thanks to the EF team for reading drafts of this. If you’d like to get trapped, start here.