Success is a terrible teacher. It convinces us that what worked before will work again, that our methods are universal, that we’ve cracked the code.
But success often happens despite our approach, not because of it. Market timing, luck, team dynamics, and favourable conditions; these get forgotten in our narratives about what made the difference.
The real trap isn’t failure; it’s assuming past success predicts future results. We double down on potentially outdated strategies, operate with yesterday’s assumptions, and solve tomorrow’s problems with old solutions.
Breaking free requires intellectual humility: questioning what you “know,” seeking disconfirming evidence, and staying curious about different approaches.
The most successful people aren’t those who never fail; they’re students of their own success, always asking not just “what worked?” but “what’s different now?”
Your biggest wins might be the biggest barriers to your next breakthrough. Question them accordingly.
We are strategists; we should think like one.
