278: You overthink every career decision
You overthink every career decision.
The problem is not that you lack information. You're drowning in it. Advice from mentors. Pros and cons lists. Scenario planning. All useful. None decisive.
The real problem is that you're trying to predict outcomes you can't control. You want certainty before you move. That's not how careers work.
Here's a brutally simple test:
Does this decision make you stronger in 12 months or just more comfortable today?
Stronger means new capabilities. Skills that compound. Work that stretches you beyond what you've already mastered. Relationships that challenge your thinking. Exposure that feels slightly too big.
Growth often comes with discomfort.
Comfortable means staying safe. The promotion that keeps you doing what you already know. The project that avoids difficult stakeholders. The role that protects your reputation. Comfort keeps you static.
Most stalled careers trace back to a pattern of choosing comfort disguised as sensible decisions.
The test doesn't make decisions easy. It makes them honest. It cuts through the bullshit and forces you to name what you're actually optimising for.
You still have to choose. You still face risk. But now you're choosing with clarity, not just collecting more data points that keep you stuck.
Next time you face a career decision, ask yourself the test question. Then notice which answer makes you uncomfortable.
That discomfort is useful information.
What career decision are you overthinking right now?
The Stuff
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- Protect your Ice Cube
Finally. Skip the Tip. A silly game that explores the dark patterns behind tipping culture.
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