World Poker Champ and Cognitive Psychologist Reveals How She Stops Retirees From Losing Everything

In this engaging episode of the Redefine Retirement podcast, host Ryan Wheless sits down with Annie Duke, a former world-champion poker player turned cognitive psychologist, delivering a masterclass on why even the most well-intentioned investors repeatedly sabotage their own retirement plans. The core problem is that our brains treat “future us” like a stranger, so in moments of panic (a 30% market drop, a scary headline), the present-self hijacks the wheel and wrecks decades of planning. Her solution is to do the hard work while everyone is calm: guide clients through vivid pre-mortem and pre-parade exercises (“Imagine it’s a year from now and you’re broke—why?” / “Imagine you crushed it while your friends panicked—why?”), let the clients generate their own answers and pre-commitments (so they actually own the plan), and reframe disciplined behavior as a rare, elite identity (“You’re one of the few who doesn’t sell at the bottom”). The result is far fewer emotional blow-ups, far less panic-selling at market lows, and retirees who actually get to live the life they spent decades saving for instead of watching it evaporate because they couldn’t resist checking the ticker on a bad day.

Visit Annie Duke’s website at: https://www.annieduke.com/

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PRODUCED BY IRONCLAD

Chapters
00:00 – Introduction: Meet Annie Duke – World-Champion Poker Pro & Cognitive Psychologist
00:54 – How Annie Went From Poker to Working With Venture Funds & Financial Advisors
02:13 – The “Category Decision” Trick That Stops Emotional Investing Mistakes
05:51 – Why Your Brain Treats Future You Like a Complete Stranger (Science Explained)
07:57 – The Real Reason 99% of Investors Panic-Sell at the Exact Wrong Time
09:43 – Do This Exercise NOW or Watch Your Retirement Disappear in the Next Crash
12:43 – Pre-Mortem: Imagine You Just Blew Up Your Portfolio – Why Did It Happen?
14:19 – Pre-Parade: Imagine You Crushed It While Everyone Else Panicked – Here’s Why
16:10 – The “You’re Special” Hack That Makes Clients LOVE Holding During Crashes
20:58 – Turn Discipline Into an Elite Identity (The Secret Sauce Advisors Miss)
28:44 – Why Clients Hate Annuities But Love Fire Insurance – And How to Fix It
31:32 – The Wedding Tent Analogy That Finally Makes Annuities Click
35:54 – The #1 Mistake Advisors Make When Selling Guaranteed Income (And the Fix)
39:58 – Markets Only Do 3 Things – Here’s How to Prepare for All of Them
42:30 – Real Client Horror Story: Sold Everything at Covid Bottom… Still in Cash Today
45:17 – Annie Duke Hasn’t Checked Her Portfolio Since Covid Began – Here’s Why
47:08 – “Ticker Watching” – The Silent Retirement Killer You Must Stop
50:29 – Kill Criteria: The Everest Turnaround Rule That Saves Retirements
54:47 – The $2 Million Poker Fold That Teaches the Ultimate Retirement Lesson
58:03 – The Hand That Changed Everything: When the Poker Boom Broke All the Old Rules
1:02:49 – Why Annie Duke Quit Poker Cold Turkey (And Never Looked Back)
1:05:00 – Final Takeaways & How Advisors Can Use This Today