Asking “what would you do differently?” gets you ten years of someone’s mistakes for free.

People are reluctant to list their achievements and surprisingly willing to list their regrets, especially to someone younger who is about to face the same choices. That one question skips past the polished version of a career and goes straight to the part with information in it. You get the expensive lessons without paying for them, which is as close to a shortcut as anything gets.

Ask it of someone doing work you might want to do. Ask it of a parent about a decision they have mentioned before. Then write the answer down, because in six months you will have forgotten the useful half.