Why keeping your options open is making you miserable

Optionality is mathematically correct for hedge funds and quietly ruinous for human beings. In this episode I break down why the “keep your doors open” advice we give ambitious people backfires, and why the irreversible choices I fear are the ones that actually make me happy.What I coverCaesar at the Rubicon: the original burned-boats decision, and why “the die is cast” still resonatesWhy optionality is genuinely correct in markets: asymmetric payoffs, real options theory, and the three principles that govern them (volatility/vega, irreversibility, and time/theta)Bezos’s one-way vs. two-way doors: and the opposite mistake we make in our private livesDan Gilbert’s photography experiment: the reversibility paradox, and why the group that could change their mind ended up less happyThe psychological immune system: synthetic happiness, and why it only switches on behind a closed doorThe four hidden assumptions that make options pricing work for copper mines but fail for a marriage, a…