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
41:56 When Jennifer Doesn’t Win a Game
44:41 How to Choose What to Microbrag About
53:32 Jennifer’s Advice on Microbragging
54:58 Outro
56:28 Disclaimer
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