When You Win, Get Curious
We investigate our losses and ignore our wins; check the other hand when you win
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 85%
Robbins demonstrates confirmation bias with a ring hidden in one hand, guessing correctly each time, then reveals he had a duplicate ring the whole time. The lesson: when we lose we become curious and investigate, but when we win we become incurious and never ask why. Success suppresses the very inquiry that would expose the trick, and in the moment confirmation bias feels like earned confidence, someone says 'I've read people since I was four' and walks away sure of a skill they never verified. The countermeasure is to check the other hand when you win, applying the same scrutiny to successes that we reflexively apply to failures. The transferable principle is that overconfidence hides in wins, so deliberately investigating your successes is where self-deception is broken.
Origin
Robbins built this into a live demonstration using two identical silver-coin rings to show confirmation bias as a felt experience rather than an abstract term.
Core principles
- 01When we lose we get curious; when we win we get incurious
- 02Success suppresses the very inquiry that would reveal how we won
- 03Confirmation bias feels like earned confidence in the moment
- 04Checking the other hand when you win breaks the con on yourself
How to run it
- 1
Catch yourself winning
Notice moments of success, which normally pass without examination.
- 2
Resist the skill story
Do not immediately credit the win to your own ability, which feels like earned confidence.
Pro tip Confirmation bias in the moment feels exactly like justified confidence.
- 3
Ask why you won
Deliberately investigate the win and look for the alternative explanation you skipped.
Pro tip Metaphorically, check the other hand when you win.
- 4
Scrutinize wins like losses
Apply the same curiosity to successes that you reflexively apply to failures.
Watch out Uninvestigated wins are exactly where you are most easily fooled.
In the wild
Robbins guessed the hidden ring correctly every time; Ferriss felt confident, then learned there were two identical rings all along. Had Robbins been wrong, Ferriss would have gotten curious, but winning made him incurious.
→ The demo made confirmation bias a felt experience, showing that wins, not losses, hide the deception.
Common mistakes
Accepting wins uncritically
Skipping inquiry on success leaves you blind to how you were actually fooled or lucky.
Mistaking bias for skill
Confirmation bias feels like earned confidence, so people walk away certain of skills they never verified.
Is it for you?
Best for
Anyone who wants to counter confirmation bias and overconfidence in their own judgment.
Not ideal for
Low-stakes wins where over-analysis wastes more than it protects.
From the transcript
“when we lose we're more curious and when we win we're less curious about why we're winning”
From the episode
#699: Apollo Robbins, The World’s Most Famous Pickpocket — Pickpocketing the Secret Service, Manipulating Attention, Famous Con Artists, The Psychology of Deception, Self-Defense Techniques, The Secret Language of Thieves, and More