There are a seemingly endless number of ways to make a living today. This optionality can paralyze young people, and rightfully so, as it all feels very permanent and important. But it doesn’t have to be that way. In the rest of this post, I'll outline an alternative way for thinking about your career.

Sampling the menu

The gist of this is pretty simple: try out different roles and environments throughout your career. Sample different values across both of these variables until you feel comfortable. Then try something else. People don’t think of their career as a 40-year expedition, but for most of us, that’s precisely the case. The reality is that it’s unlikely the first thing you pick up will be what you’re best at or fulfills you the most. So why not explore a bit?

If you meet a certain threshold of privilege as a knowledge worker, then you can hop from role to role fairly seamlessly in today’s work culture. Remote work going mainstream has certainly helped this, as you can hop from job to job without having to pick up and move. So why not sample the menu a bit before you pick the entree you'll be having for years and years? Try different roles in different environments for 1-3 years each, or until the learning curve flattens, or until you get bored or dissatisfied. Then try something else.

Why this is nice

  • You develop a wide array of skills and learn what you enjoy most.
  • These skills interact with eachother in ways you may or may not foresee. Even if you won’t be a designer long-term, that design skillset will make you a better PM or SWE in the future.
  • You can’t predict the future, so it makes you more resilient to change and better at learning. If GPT-12 comes along and automates roles that we know and love today, then you have other skillsets to fall back on.
  • It’s fun! If you enjoy the road to 80% competency more than the road from 80% → 90% competency like I do, then picking up new skills and learning the terrain is an energizing and fulfilling way to spend your days.

Why this isn't all that nice

  • It’s more work. The effort you put in to optimize a certain skillset is going to be less stressful and more comfortable than picking up something totally new. Doing bootcamps, courses, etc. requires a certain degree of daily commitment that has to be internally motivated and driven forward. There are days where it’s exhausting.
  • Your ‘competitors’ will be more specialized. If you’re extremely competitive and want to be the best at one thing, this approach may not be the best one for you. You’ll watch as your colleagues and friends specialize further and are flat-out better with more experience than you at certain tasks.
  • You won’t make as much money. At least in the short-term, hopping from role to role will usually require you to forgo a raise or even in some cases, take a cut. This makes sense. From an on-paper assessment, a L2 PM is less valuable to the company than a L5 Sales Engineer will be. They won’t be as effective, and therefore may not get paid as much.
  • Your title won’t grow and you won’t seem as impressive. It’s way easy to gain respect of your colleagues and friends when you stay in your lane, climb the ranks, and your title grows accordingly. Introducing yourself to someone new at a networking event can be an ego hit.

Wrapping up

Unintentionally, I've ended up doing this in my own career:

  • Data science for 2 years at bigger companies
  • Growth for 2 years at a small startup
  • Product for 3 years at a medium-sized startup

I've enjoyed all of these different roles and company sizes, all for different reasons. However, the one commonality between them was that I enjoyed learning new things. That's what I'm optimizing for above all else. You don't have to "sample the menu" to do that, but for those that are ambitious, become bored easily, and are motivated by up-leveling skills, it's a very viable option.

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