The world is a very malleable place. If you know what you want, and you go for it with maximum energy and drive and passion, the world will often reconfigure itself around you much more quickly and easily than you would think.

Treat your career as a portfolio of jobs/roles/opportunities, not as a sequence of standalone bets. Any single opportunity should be evaluated against the return/risk profile of all the other risks you'll take across a 50+ year career — which makes individually 'risky' moves often look obviously correct.

Opportunities fall into two buckets: those that present themselves to you, and those you go create. The dividing line between people whose careers go up like a rocket and those whose don't is whether they say yes when a senior colleague, a former manager at a hot startup, or friends headed to Denny's at 11PM to brainstorm a company come calling.

Right out of school — low burn rate, geographic flexibility — is the time to take income risk. Always take the job that best develops your skills and gives you valuable experiences, regardless of salary. This is not the time to play it safe.

Risk allocation by life stage.

Working for a big company is much riskier than it looks. You're subject to impersonal layoffs at any time, you develop skills more slowly, and after five or ten years you realize your experience is only relevant for jobs at other big companies — and then you have a real problem.

Quoting Aaron Brown on hiring traders: 'What I listen for is someone who really wanted something that could be obtained only through taking the risk... It's not even important that she managed the risk skillfully; it's only important that she knew it was there, respected it, but took it anyway.'

Quoting Taleb: 'Seize any opportunity, or anything that looks like opportunity. They are rare, much rarer than you think... If a big publisher (or a big art dealer or a movie executive or a hotshot banker or a big thinker) suggests an appointment, cancel anything you have planned: you may not see such a window open up again.'

Jumping fields (e.g., enterprise software to consumer internet) is almost always a risk worth taking. Standing pat and being unhappy has risks of its own — and it's awfully hard to be highly successful in a job or field where you're unhappy.