EXAMPLE: "Should I leave my corporate job to go freelance?" 1. 10/10/10 10 min: Terrified about losing the paycheck. 10 months: If freelancing works, liberated. If not, still learned what I'm capable of. 10 years: The regret of never trying will weigh more than a failed attempt. 2. REGRET MINIMIZATION At 80, you'll regret playing it safe. The corporate job will always exist. The window of energy to try something bold won't. 3. REVERSIBILITY Freelancing is a two-way door. Skills and resume don't disappear. Returning to corporate is possible. The one-way element: golden handcuffs compound the longer you stay. 4. OUTSIDE VIEW "You clearly want to do this or you wouldn't keep bringing it up. The real question isn't whether to leave — it's whether you've set up enough runway." SYNTHESIS: Leave — but with preparation. Build 6 months savings and land 1-2 clients before quitting.