Reconsidering Career Optionality

Play a game with your career that offers the possibility of a win for you. Just be ready (mentally and financially) to accept that with a chance to win, you may also have a chance to lose—earning little to nothing despite your best efforts.

Nassim Taleb suggests targeting the two extremes of the career spectrum at once. On one end of the barbell, you play it safe with a secure, staid job. On the other end, you take highly speculative risks. In the middle, as little as possible.

Many young people default to tracked behaviors where they choose the safer, consensus “next step” over and over again They keep pushing decisions further out into the future, then get into their mid-30s and have no idea how they ended up where they are. Society must also encourage people to be “spikey” instead of only encouraging people t