My answers to questions people have asked me.

Should I go deep or broad in my career?

Early in your career, sample actively, i.e. go broad. Commit to depth when process (not just outcomes) energizes you. Read Range (David Epstein, 2019).

How do I explore when I’m stuck in a role?

Say yes to stuff you don’t like. You’ll do what you like anyway. For breadth, you need the opposite. You’ll learn:

  1. New things you enjoy. (Do you enjoy the same things you enjoyed 10 years ago?)
  2. How to enjoy stuff you don’t like. (A useful meta-skill.)
  3. How to get out of stuff you don’t like. (Another useful meta-skill.)

How do I make boring work more fun?

  1. Do the minimum on boring tasks. Spend more time on fun adjacent tasks.
  2. Make boring work more fun. (I once wrote an RFP so dry no human could read it. So I turned it into a 430-character poem via the first letter of every page.)
  3. Don’t assume what’s boring now will be boring later. (Testing bored me until Simon Tully explained that it’s detective work!)

What skills should I learn?

  • Ignore your passions. Pick what’s rare and valuable.
  • In winner-take-all markets (e.g. sports, sales, research), double-down on the most important skill. Otherwise (e.g. consulting, entrepreneurship), stack related skills to build rare + valuable combinations.
  • In rapidly changing fields (e.g. technology, digital marketing), learn how to learn fast. In stable fields (e.g. law, medicine), gain knowledge.
  • In your early career, bet on emerging technical skills. In late career: invest in slower-decay judgement & leadership skills.

What projects should I work on?

Choose projects where the process of getting good at them solves a problem you care about for people whose judgment you respect.

Short Runway Long Runway
Low Capital Skills-first. Optimize for learning. Pay « Best mentors. Explore widely. Many small bets, diversify
High Capital Leverage & monetize, preserving optionality. Moonshots: high risk + upside. Startups, books, research.
  • For fast industries (tech, AI, media): short, intense explorations since skills depreciate faster.
  • Slow-clockspeed industries (law, medicine, infrastructure): specialize deeply since skills last longer.
  • Regulated industries (pharma, finance): Build credibility with gatekeepers. Invest in compliance, quality, and trust-building.