Strategic Whimsy & Joyful Leadership with Bob Goff

When I sat down with Bob Goff for this episode of Play for Performance, I knew we were in for something special. Bob isn’t just a New York Times bestselling author—he’s the founder of the Love Does nonprofit, a global difference-maker, and quite possibly the most joy-filled human you’ll ever meet. He’s also a master of what he calls “strategic whimsy”—finding creative, unexpected ways to turn big dreams into real-world impact.

From building schools in conflict zones to, yes, acquiring actual giraffes for a university in Uganda, Bob’s stories will make you laugh, tear up, and rethink how you approach your own work and life. As we talked, we explored why anticipation is a secret superpower, how playfulness can transform even the most serious work environments, and the importance of keeping “the big things big and the small things small.”

If you’ve ever wanted to bring more joy, creativity, and purpose into your leadership—or if you simply need a reminder that meaningful work doesn’t have to be boring—this conversation is for you. Bob and I share practical ways to spark more meaning in your day, inspire your team, and create a ripple effect that goes far beyond the office.

So grab your favorite notebook (Bob will insist on it!) and join us for a conversation that will leave you smiling, inspired, and maybe even ready to toss a little more confetti into the world.

Chapters:

00:00 - Introduction
00:09 - Reunion of Released San Quentin Inmates
06:34 - Witch Doctor Justice Dilemma
07:45 - Honey Trumps Vinegar in Disputes
11:50 - Inspiring Nashville Fundraising Event
13:50 - Concierge Spirit: Helping on Your Way
17:25 - "Love Your Local Neighbor First"
23:10 - Creative Holiday Pottery Plans
27:17 - "Lost Camera Returned After Adventure"
28:05 - "Navigating Ambiguity in Lending"
31:39 - Supportive Outreach and Connection
35:27 - Learning to Fly in Remote Canada
39:43 - "Opinions vs. Experiences: A Lawyer's View"
42:29 - "Play for Performance: Episode Wrap"
42:32 - Outro

Quotes:

"Embrace what's possible and take the leap. True joy comes from seizing the opportunities around us."- Bob Goff

"Break free from traditional work norms. Silence the noise and follow your true passion to achieve your dreams."- Jolynn Ledgerwood

Key Takeaways

Live with Anticipation
Strategic Whimsy Wins
Focus and Flow
Play Transforms Serious Work
Model Self-Awareness
Be the Sherpa, Not the Star
Celebrate Small and Big Moments
Choose Experience over Opinion
Generosity and Connection Matter

Connect with Bob Goff:Company Website: http://lovedoes.org/
Personal Website: http://bobgoff.com/

Connect with the Host:
Linkedin: https://www.linkedin.com/in/jolynnledgerwood/
Website:https://elevateyourtalent.co/

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