Find someone who'll take a chance on you, and work like hell to prove them right

Careers are weird

We end up spending the majority of our lives working on a short list of things with a few hundred people. Each time we change jobs, it's a moment of extreme leverage - a decision point that literally changes the trajectory of the rest of our lives. I'm (checks watch) wrapping up the first third of my career, and this advice is directed towards those earlier in their careers, although it may be useful to those further on as well.

I've had tremendous fortune getting the chance to work on cool things with interesting people at a consistent rate so far. Some of that fortune can be attributed to hitting the socioeconomic lottery at birth, but there's a lot of upper-middle-class white dudes who are unhappy with their careers, so that can't be all of it. I truly believe a big chunk of the reason I am where I am is my job choice philosophy. It's the title of this essay, but I'll write it again:

Find someone who'll take a chance on you, and work like hell to prove them right.

I'll break what that means and why it's important in this essay.

Find someone who'll take a chance on you

Like it or not, our careers are based on the opportunities given to us by others. As an employee interviewing for a job, you're submitting a description of yourself to a system, hopefully with a human in the loop, that reviews your description and determines whether you are the right person to contribute to the team's efforts. The decision is made along the rubric of "will person A be able to handle responsibilities X, Y & Z?".

At the core, that's all it is. They're setting their expectations for you based on the role that's open. That bullet list of responsibilities is the only guaranteed list of items you'll get to do at the job. When you apply to a role that you are cleanly qualified for, you are offering to step into a box that you already fit snugly into. Additionally, you are self selecting into a team that looks at you and says "yep, they've done this exact work before, that's what we need."

There's no guaranteed room for growth!

Sometimes, you'll get an opportunity to prove yourself on the job and get a bigger box to grow into, but more often than not, you're signing up for a consistent, predictable, standard career path. Might be great for some, but not for me.

I've had the distinct honor time and time again of finding hiring managers who've hired me 'up' into their roles, and each time the conversation on their end has been something along the lines of "he hasn't done this exact work before, but let's give him a shot".

Granted, I've also had lots of hiring managers say "you haven't done this work before, so we've decided to move forward with another candidate". That sucks, and will always sting in the moment, but in retrospect is also a great stroke of luck. Managers unwilling to take risks on their team are probably not operating from a space that allows for the same level of growth.

The hiring managers who do take a chance on you create an amazing space of potential. They're essentially looking at you, looking at the role, and saying "this is hard, but I believe in you". Having grown up in sports, there's a direct parallel to the best coaches I played for. This not only made me feel more committed to the team, it also pushed me to work harder than I thought possible.

Work like hell to prove them right

This is the part that might lose some folks, but it's arguably the more important half of the essay. Once you've gotten that wild opportunity, you owe it to the people who took a chance on you to push for great things.

Careers are long. The spikes of joy and excitement that come from a cool new job fade away over time, and jobs all revert to the mean. The Hedonic treadmill of life means that anything amazing (or terrible) drifts towards becoming normal everyday life after a bit. So how do you keep the vibes high? You give yourself something (or someone) to fight for.

In sports, you'll hear about the coach who pins up a quote from the rival team in the lockerroom the week before a big game. Michael Jordan famously created beef with opposing players, to drive himself to play harder. Both of those things point to the same underlying psychological trick: When we have an external mtoiviating factor, it can push us further than just "I want to do a good job".

And who better to motivate you, or to push for, than the person who took a chance on you in the first place? If you win, they win, and you owe it to them to at least try. But what does winning look like?

Take on the extra project. Work later than your teammates. Work earlier than your teammates. Take another pass at the review. Spend Saturday thinking about how you could make things better. Spend Sunday making things better. Don't forget to pause, breathe, and reset when needed, but work like hell to prove them right.

This isn't some hustle-core thinkpiece, though - the reasoning behind this approach is both self-serving and valiant. When you prove this person right, they're more likely to take risks on people in the future. You're not only serving your own career with this approach, you're creating opportunities for more non-run-of-the-mill folks to swing upwards in the future.

As I progress into this next phase of my career, I'm going to get more opportunities to take chances on people. I sincerely hope that they'll work like hell to prove me right.