On Making Better Career Decisions

If I could go back to school, particularly when deciding what to study, I’d make a very different decision. The majority of people I speak to say the same thing. But most decisions don't come with second chances.

If I want to make good career decisions now - the jobs, problems, and causes to give my attention to - how do I do it? Here are a few ideas off the top of my head, I'd love to hear yours:

1. Talk to people that are currently doing what you think you want to be doing. Get very very curious and ask them a lot of questions. Be really honest with yourself and decide if that’s something you want to be doing. You probably already know about the good parts of the job (that’s why you want to do it), so try to uncover the bad parts and decide if the good outweighs the bad.
2. Be more ambitious. Most people aren't as ambitious as they should be. Too many people settle for average. If you rarely fail, you probably aren't being ambitious enough. Failure shows you where the boundaries of your abilities lie, and if you never fail, you're playing too far within those boundaries. Failure is like a dial for ambitiousness, crank it up.
3. Do something audacious. Sixteen year olds aren't supposed to write novels. Lawyers aren't supposed to start billion dollar technology companies. So if you try, anything you achieve is on the plus side of the ledger; if you fail utterly, you're doing no worse than expectations, and you'll have a story to tell. Don't underestimate the power of a good story.
4. Look for smart people working on important problems and spend time with them. Smart people are more introspective about what they work on. They can work on almost anything they want, so they have to approach each option with scrutiny. This scrutiny will spill over into your decision-making and improve it in the process.
5. Be wary of optionality [1]. People work insanely hard to accumulate options for the future, instead of figuring out what they really want to do and doing it. That's like spending your whole life filling up the tank without ever driving. It lets you off the hook of doing the hard work of figuring out what it is you want and what you should be doing with your life.
6. Be ridiculously optimistic. Individuals and teams can achieve monumental things that change the world permanently. Most people benefit from taking an optimistic view and acting as if individuals can make a very big difference. There’s little downside from being too optimistic, and a whole lot of upside if it proves right.
7. It's ok to look dumb. The goal is not to look smart the whole way. Better to look dumb for a bit, but genius at some point, than look merely decent the whole way by taking the safe path.

Footnotes

[1] This should probably be a post of its own. Recommended reading here and here.