Although people considering the option of leaving the default path can list hundreds of things that might go wrong, they struggle to talk about the fears behind those risks. In hundreds of conversations with people, I’ve found that these fears fall into one of the following five areas: Success: “What if I’m not good enough?” Money: “What happens if I go broke?” Health: “What if I get sick?” Belonging: “Will I still be loved?” Happiness: “What if I am not happy?” During my first few years of self‑employment, these fears overwhelmed me, but Tim Ferriss’ “fear setting” reflection exercise helped
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