The Grateful Podcast with Jack Wagoner
Episode 81
Guest: Jon Bassford
What if your greatest leadership strength wasn’t authority, experience, or intelligence—but curiosity?
In this episode of The Grateful Podcast, Jack Wagoner sits down with Jon Bassford—entrepreneur, operations strategist, TEDx speaker, and author of The Curious Leader—to explore how asking better questions can unlock innovation, deepen self-understanding, and transform not just your team, but your life.
They dive into the chaos and beauty of curiosity: how it can feel overwhelming, how it can set you free, and how it might just be the missing piece in both solopreneurship and scaling businesses alike. If you’ve ever felt pulled in too many directions, questioned your path, or sensed that there’s more to life than just “doing the job”—this episode is for you.
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🎯 Topics Covered:
• Why curiosity is the ultimate superpower
• The danger of chasing the wrong outcomes
• How to reframe purpose as a verb, not a destination
• Surface-level curiosity vs. deep, wonder-driven exploration
• The power of reflection, meditation, and self-inquiry
• Building a life from the inside out (and staying sane while doing it)
• Scaling as a solopreneur and knowing when to let go
• How gratitude and ambition create a meaningful, sustainable life
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🌐 Connect with Jon:
🔗 Website: https://jonbassford.com
💼 Consulting: https://think-lateral.com
📲 Instagram: @jon_bassford
📕 Book: The Curious Leader on Amazon: Buy Here
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⏱️ Timestamps:
00:00 The Power of Curiosity in Leadership
03:10 Discovering Curiosity as a Superpower
06:45 Breaking Free from the Status Quo
10:36 Curiosity vs. Chaos
13:00 Asking the Right Questions
16:00 Reframing Purpose as a Verb
20:30 Overcoming Overachievement with Gratitude
24:00 Meditation, Stillness, and Inner Work
28:40 Solopreneurship in the Age of AI
33:10 Building an A-Team (Not Just A-Personalities)
36:30 Why Impact Beats Income
40:50 The Law of Attraction and Letting Go
43:40 Narrative Identity and Rewriting Your Life
46:15 Balancing Goals with Presence
49:00 Buddhist Philosophy and the Journey of Becoming
52:00 Book Rec: Siddhartha by Herman Hesse
53:00 Final Reflections and Where to Find Jon
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📺 Watch or Listen Anywhere
🎧 Spotify / Apple Podcasts:
https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061
🔔 Subscribe for weekly conversations with soulful thinkers, dream-chasers, and deep-feeling builders.
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🧠 More from Jack:
📬 Newsletter (Magic, Meaning & Momentum):
https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
📸 Instagram: @jack_wagoner_
🎯 1:1 Coaching & Dream-Chasing Guidance:
jackcwagoner@gmail.com
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💬 If this episode spoke to you:
• Share it with someone who lives curiously
• Leave a review—it helps others find this show
• DM me your takeaways on Instagram—I’d love to hear from you
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🎙️ About Jack:
I’m an 18-year-old high school student with a big dream: to show the world that you can be grateful and ambitious at the same time. Through The Grateful Podcast, I explore what it means to live a meaningful life—one deep conversation at a time.
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