Friday Oct 31, 2025

Episode 40: You're Not Bluffing Big Enough

What does it take to trust your instincts when the odds are stacked against you?

How do you balance strategy, intuition, and risk without letting self-doubt creep in?

How do we celebrate our wins in an authentic way?

Jennifer Shahade is a three-time US Women’s Chess Champion, professional poker player, and author. She brings world-class lessons from chess and poker to everyday life, showing how to merge confidence and calculation so you can make better choices under pressure.

What we cover in this episode:

Why if you’re never caught bluffing, you may not be going big enough in poker, in work, or in life.
How chess teaches presence, empathy, and better decision making by widening your options.
This week’s micromoment, Micro-Brag: practical ways to name wins, build a “confidence primer,” and share accomplishments with authenticity.

Make smarter decisions, have stronger self-trust, and handle uncertainty with real strategies in work and life.

Preorder her new book: Thinking Sideways

00:00 Intro

01:14 Meet Jennifer Shahade

05:34 Be Comfortable with Risk

07:08 Lesson #1 from Poker: Bluff Bigger

10:11 Lesson #2 from Poker: Balance and the Quality of Your Decisions

13:55 Lesson #1 from Chess: Seeing Possibilities and Staying Present

18:38 Lesson #2 from Chess: Time and Decision-Making

22:19 Thinking Sideways and Applying Game Strategy to Life

30:51 Confidence is Dynamic, Not Fixed

36:27 Micro-Moment of the Week: Microbrag