Don’t Settle

Playing it safe is riskier than you think

Last week, a friend told me he was taking a "safe" job instead of building something he deeply cared about. He felt he needed more experience before taking a leap. I asked, "What experience do you need to start?" Silence.

Just like skipping to the end beats following prescribed paths, choosing the hard thing often beats the safe one. Every "prerequisite" is an opportunity to settle. Every "right path" is someone else's map.

Bezos calls these Type 1 and Type 2 decisions. Type 2s are reversible—like testing a feature or trying a new role. Type 1s are permanent—like spending years on the wrong path. Yet we often treat reversible choices like permanent ones, paralyzed by decisions we can easily undo.

The math gets even more interesting when you consider asymmetric upside. Taking the "risky" path might cost you a year of salary if it fails. But if it works? It could change your entire trajectory. The downside is limited, but the upside isn't. Meanwhile, the "safe" path has a clear ceiling and an invisible cost: the weight of regret.

Most people avoid hard things because they're hard. They mistake difficulty for risk. But difficulty isn't risk—it's the filter that keeps others from attempting what you know you can achieve.

Your future self won't judge you for failing. They'll judge you for not trying.