Seek the Asymmetric Bet
Is the upside many times the downside? And is the downside survivable?
Before committing to any significant move, write two numbers: What's the most I can lose? What's the most I can gain? If the potential upside is many times the downside, and the downside is survivable, you've found an asymmetric bet. Take it. If the downside is catastrophic regardless of the upside, walk away.
You're evaluating an opportunity, investment, career move, or strategic bet and need to assess whether the risk profile justifies commitment.
Both outcomes are roughly proportional and the decision comes down to preference rather than asymmetry.
Why it works
Decisions depend on payoff shape as much as success probability. A low-probability move with large upside and capped downside can be worth taking when failure is survivable.
A useful risk question is not “will this work?” but “what is the payoff shape?” Risking £1 to potentially gain £100 can make sense even with a low success rate, provided you can make similar bets repeatedly and the losses stay small. The important constraint is survivability. A bet with bankruptcy on the downside is not asymmetric in any useful sense, because one loss ends the game. Look for positions where failure is affordable and success changes the range of future options. Those bets deserve more attention than comfort alone would give them.