It's tough to write about career advice. Every case is different and like most hard problems, there are few universal truths. The below quote from How to Do What You Love, one of my favorite Paul Graham essays, sums this up nicely:

When you're young, you're given the impression that you'll get enough information to make each choice before you need to make it. But this is certainly not so with work. When you're deciding what to do, you have to operate on ridiculously incomplete information

Speaking of thinking, I've been doing a lot of it lately. I recently decided to join Hugo, a fast-growing startup creating a smarter interface for meeting notes. This is a pretty big move for me. Eventually, I simplified my thinking down to a framework for assessing current and future career opportunities.

The Building Blocks

You'll be relieved to hear that this framework was inspired by plenty of people smarter than I am. Reid Hoffman's advice to simplify complex decisions down to only the most important dimension from an episode of Masters of Scale was a breakthrough for me.

This basically means that you care about a million things when assessing decisions like career opportunities: money, location, team, product, role, and more. Forget all of that. Big decisions abide by the power law. Focus on only the few most important things to you.

Another key piece of inspiration was Daniel Pink's thinking around motivation from his book Drive, which I highly recommend. Pink describes the evolution of motivation from autonomy to mastery to purpose. Each element is a layer on top of the last.

With the current and future transition to more knowledge workers, autonomy will become more of a given. It will go without saying that you are given ownership of the task and are responsible for the outcome. This mean that more motivation will be driven by mastery and purpose than ever before.

How to Make Career Decisions

There are a million variables to consider when you're making a big career decision. Keeping the power law in mind, I've simplified things down to only the most important factors: learning, alignment, and impact.

These are especially applicable if you are ambitious and early in your career, though the same principles apply to everyone. If you put all of this together, you come up with the following question:

Where will you have an impact, while learning things that align with your goals?

This is pleasantly concise, but let's break down each part of the question in more detail since, hey, this is kind of important.


Albert Einstein reportedly described compound interest as "the most powerful force in the universe." In hearing this, it's common for our brains to go straight to investing. Compound interest can also be applied in the context of learning. Sam Altman drives this point home in his essay, How to Be Successful:

You don't want to be in a career where people who have been doing it for two years can be as effective as people who have been doing it for twenty—your rate of learning should always be high. As your career progresses, each unit of work you do should generate more and more results.

What you learn today will act as a launchpad for what you learn tomorrow. When thinking about career decisions, ask yourself, where can you build the best launchpad?


Planning is often a futile exercise. When thinking about careers, Marc Andreessen tends to agree:

Trying to plan your career is an exercise in futility that will only serve to frustrate you, and to blind you to the really significant opportunities that life will throw your way.

Andreessen goes on to say that you should focus on improving meaningful skills and keep an eye out for big opportunities. There's no way to reliably know where we will be 10 years from now.

In order to follow Marc's advice, you don't need a roadmap. You just need a general direction. Once you have an idea of where you want to be one day, you can make sure that you are developing skills that are relevant to that vision and keep an eye out for opportunities that will take you closer.


In the context of the universe, we are all microscopic entities. It's easy to begin to think that we can't do anything meaningful. There's undoubtedly some truth to this, but it's also a dangerous way of thinking. We don't have to change the course of the universe to have an impact, sometimes we just need to put a ding in it.

Most of us spend more than half of our productive hours at work. That time should matter.

There's two ways to achieve impact. First, you can go somewhere that you can move the needle in a meaningful way. This might mean a small or medium-sized company as opposed to joining a larger corporation.

The other way to find impact is working on something you care deeply about. If you are helping move your company or product towards a new ideal, then that can also be pretty powerful. It may take some exploration to find which of these is right for you, but once you find it, you'll know.


It certainly wasn't easy for me to get here. Deciding to move on from a role that I already really enjoyed was difficult. It wasn't a super fun decision-making process to be honest, but I'm coming away from it with an exciting new chapter and a simplified framework for these decisions in the future.

  • Where will the rate of learning be the highest?
  • Where will the things I'm learning align with my goals?
  • Where will I have the greatest impact?

If you can find somewhere that hits on all of these points, you have something pretty special. Even being in the place to make a decision like this is a blessing by itself. It might be hard, but nothing worthwhile is easy, right?

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