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How I think about career

I think it’s ridiculous to expect anyone 21 or younger to know what they want to do for their career.

This is how I answered that question at the family barbecues over the years:

On my learning gap year, I spent a lot of time working closely with Alex Brogan—a career maximising geek and who’s shaped much of my thinking on this topic.

Some of my thoughts:

  1. Explore, then exploit

    The limiting factor is usually a lack of data. Treat it like a science experiment: list possible hypotheses, then test them quickly with minimal commitment. Your goal? Reduce that list of options.

  2. Question mimetic desire

    We inherit the ambitions of those around us, from family, friends, and online gurus. Ask yourself:

    “If I weren’t afraid of others’ opinions, what would I choose?”

  3. Be willing to work for free

    Without experience, this is an easy way to get your foot in the door.

  4. Ignore sunk costs

    Past time, effort, and money shouldn’t dictate your future. If you got hit by a bus tomorrow, would your previous choices matter? Probably not, so I’d change my mind without much thought.

  5. Optimise for working with specific people

    This is how I’ve approached every job experience I’ve had. Find someone you want to learn from and find a way to work for them.

  6. Be willing to take on risk

    At 18-21, you have the least commitments you ever will. If things fail, there’s little downside compared to later in life.

  7. Try and find something that feels like play

    You’ll spend at least a third of your life working. You may as well enjoy it.

  8. Be solid on the vision, flexible on the details

    Once you have some experience and reduced your list of options, it’s helpful to create a general direction you want to go. But don’t limit randomness and serendipity on how to get there.

A learning gap year can be helpful to figure out the above, and don’t forget to send lots of cold DM’s and emails.