Facing a dead-end job, Amy Weaver chose to resign without another position lined up, guided by the principle: "First you leap and then you grow wings." This counterintuitive approach of creating a void, though terrifying, can be the necessary catalyst for finding a better opportunity, as it was when Salesforce called two months later.
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Quitting your job, if financially feasible, provides the 40+ hours per week needed for a high-intensity, value-driven job search. It transforms you from a distracted employee into a focused, available strategic asset. This focus can significantly shorten the search duration, offsetting the perceived risk.
A fixed long-term career plan can be paralyzing. Instead, view your dream future as being on the other side of a lake covered in lily pads. Your job is to leap to the next immediate opportunity that energizes you, creating a flexible, compounding journey without the pressure of a grand vision.
Pursuing a more fulfilling career doesn't require risking financial ruin. Instead of taking a blind leap, you can vet a new direction by "trying it on"—shadowing professionals, conducting informational interviews, and testing the work in small ways to understand its reality before making a full transition.
When you take a professional risk, the result is binary: either you succeed, or you fail. While failure might sting, it provides a definitive answer, freeing you from the mental anguish of wondering 'what if.' Both outcomes are superior to the paralysis and prolonged uncertainty of inaction.
If you're miserable in a job but financially unstable, 'just quitting' is impractical. The solution is a 'practical quit': aggressively apply to hundreds of other jobs first. This channels frustration into massive action instead of dwelling in complaints. It prioritizes securing an alternative—even an imperfect one—before leaving a stable paycheck, combatting the inertia of complaining.
Instead of "burning the ships," treat potential career changes as experiments. By starting a new venture as a side hustle without financial pressure, you can explore your curiosity, confirm it's a good fit, and build a "safety net" of confidence and proof before making a full leap.
When facing a major career crossroads, the goal isn't to find the objectively "best" option, as it's unknowable. The key is to make a decision based on intuition, commit to it fully, and refuse to entertain "what if" scenarios about the paths not taken.
True long-term career growth isn't about climbing a stable ladder. It's about intentionally leaving secure, successful positions to tackle harder, unfamiliar challenges. This process of bursting your own bubble of security forces constant learning and reinvention, keeping you relevant.
A creative director describes getting fired as "brilliant" because the failed role introduced him to direct marketing just as it was becoming a dominant force. This mistake proved more valuable than succeeding in a traditional, less relevant field, leading to more learning and better connections.
When deciding whether to leave a stable job to start Amazon, Jeff Bezos asked which choice he would regret more at age 80. People are far more haunted by the opportunities they didn't take than the ones they took that failed. This is a powerful mental model for making bold career leaps.
