The Ambitious Generation

Send us Fan Mail

You’ve hit your goals—but why does it still feel like something’s missing?

In this solo episode, Jack Wagoner flips the script on traditional goal setting and reveals why chasing external achievements will never bring the fulfillment you’re looking for. From his own story of getting into Northeastern to reaching 10K podcast downloads, Jack shares the harsh truth: our goals aren’t broken—our relationship with them is.

This episode explores:
 • Why outcomes never lead to lasting peace
 • How to reverse-engineer your life based on how you want to feel
 • The “Be → Do → Have” model that actually works
 • How to escape the empty high of constant achievement
 • A practical challenge to help you redefine your goals today

Whether you’re chasing success, growth, or clarity—this episode will help you ground your ambition in presence, alignment, and lasting fulfillment.

The Grateful Podcast with Jack Wagoner
Episode 89

Support the show: https://www.buzzsprout.com/2302168/support

Chapters:
00:00 Redefining Goals: The Problem with Traditional Goal Setting
02:32 The Emotional Connection: Why Feelings Matter More
05:19 Be, Do, Have: A New Approach to Achieving Fulfillment
08:07 Shifting Focus: From Outcomes to Feelings
10:47 Living in the Present: Balancing Gratitude and Ambition

📺 Listen on your favorite platform:
Apple Podcasts: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061
Spotify: https://open.spotify.com/show/5EsTEpQAjU4BxUrDoFyZ6b

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner

Episode 88

Guesting Jess Prudhomme

At 35, Jess Prudhomme had checked every box: corporate success, a polished identity, a picture-perfect marriage. But beneath the surface was a quiet ache — the haunting question, “Is this really me?”

In this raw and powerful conversation, Jess shares how her greatest detours — divorce, quitting her job, walking away from security — were not breakdowns, but breakthroughs. Together, we explore:

• Letting go of identities that no longer fit
  
  
  
• Why ambition can be a mask for fear
  
  
  
• How to follow a gut feeling without a plan
  
  
  
• Why success is nothing without alignment
  
  
  
• How to trust yourself when everything feels uncertain
  
  

Chapters:
00:00 Introduction to the Journey of Self-Discovery
03:05 The Courage to Pivot: Leaving the Corporate Grind
05:57 Unraveling Identity: Who Am I Without My Job?
08:57 The Importance of Being Present
11:27 Navigating Relationships and Friendships
14:38 Fear-Driven vs. Purpose-Driven Ambition
17:28 The Role of Therapy and Introspection
20:33 Embracing Stillness and Rest
23:45 The Power of Gratitude in Life's Detours
26:36 Transforming Adversity into Growth
29:34 The Journey of Self-Reclamation
32:28 Trusting Your Gut: Making Decisions for Yourself
35:30 The Art of Letting Go
38:34 Celebrating Non-Traditional Success
41:24 Finding Fulfillment Beyond External Validation
44:25 Exploring Life's Possibilities
47:12 Inspiring Others Through Vulnerability
50:08 The Duality of Gratitude and Ambition
53:11 Conclusion: Embracing the Journey Ahead

Jess is the host of The Great Detour Podcast, and her story is a reminder that you are not your job, not your title, and not your performance. You are enough — even in the in-between.

🎧 Follow Jess:
Instagram: @thegreatdetour
Website: https://thegreatdetour.com
YouTube: https://www.youtube.com/@TheGreatDetourPodcast

—

If this episode moved you, share it with someone who’s navigating uncertainty.

Subscribe, rate, and review to help us keep creating magic.

#TheGratefulPodcast #JessPrudhomme #TheGreatDetour

📺 Watch the full episode on YouTube:

https://youtu.be/r1N4agSN0k0

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 87
Guesting Joshua Dean Church

Born with a collapsed lung and told he’d never be an athlete, Joshua Dean Church defied the odds—completing an Ironman and sending the finish line photo to the doctor who once doubted him. A Forbes 30 Under 30 entrepreneur, Josh built a $20M company in three years, only to shut it down when it no longer aligned with his purpose.

In this deep, soulful, and fiercely honest episode, Josh shares:
 • How adversity isn’t in the way—it becomes the way
 • Why leading others starts with leading yourself
 • The 5 pillars of modern leadership
 • His journey from black sheep to heart-centered leader
 • The dance between faith, intuition, and ambition
 • What “living what you rap about” really means

We talk journaling, mental toughness, spiritual growth, and how to find the next step when you feel completely lost.

Chapters:
00:00 Embracing Pain and Adversity
03:55 The Journey of Intuition and Inner Guidance
06:48 Navigating Business Failure and Growth
09:47 Lessons from Failure and Leadership Development
12:46 The Shift in Podcast Focus: Leadership
15:41 The Importance of Historical Leaders
19:18 Defining Modern Leadership
22:16 The Dance of Surrender and Action
36:55 The Power of Gratitude and Ambition
42:55 Finding Balance: The Middle Path
49:17 Navigating Misalignment and Seeking Clarity


📍 This is one of the most important conversations we’ve had on the podcast. Listen closely.

Find Josh:

Website: https://www.joshuadeanchurch.com/

Instagram: https://www.instagram.com/joshuadeanchurch/

LinkedIn: https://www.linkedin.com/in/joshchurch

YouTube: https://www.youtube.com/@joshuadeanchurch

The Way You Lead Podcast: https://podcasts.apple.com/us/podcast/the-way-you-lead/id1475360470

📺 Watch the full episode on YouTube:

https://youtu.be/r1N4agSN0k0

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 86

Support the show: https://www.buzzsprout.com/2302168/support

In this solo episode, I open up about what it’s really like to choose the long game at 18 years old—pursuing my podcast, building a climbing clothing brand, and saying no to a typical summer job.

I talk about comparison traps, jealousy, creative isolation, and how I’ve found freedom by building a life that looks different—and loving it anyway. I also share the daily habits that make me more productive (even if they look “unproductive”), and why prioritizing joy, nature, and self-reflection has made all the difference.

Whether you’re carving your own path, chasing something unconventional, or just trying to stay motivated—this one’s for you.

⚡ Plus, I share my personal challenge: hitting 100,000 podcast downloads before I start college at Northeastern on August 31st.

Chapters:
00:00 Embracing Unique Goals and Discomfort
02:51 The Long Game: Building for the Future
05:45 Finding Freedom in Work and Life
08:44 Prioritizing Self-Care for Productivity
11:38 Mission for Growth: Podcast Goals and Support

📺 Watch the full episode or listen on your favorite platform:
Spotify/Apple: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 85
Guesting Carmen Turner Schott

In this episode of The Grateful Podcast, I sit down with Carmen Turner Schott, a licensed clinical social worker, trauma therapist, and professional astrologer who has worked for over 25 years in the U.S. Air Force. Together, we explore the intersection of astrology and psychology, challenging assumptions and expanding perspectives.

Initially skeptical, I came into this conversation with questions—and I left with new insight into how astrology might serve as a tool for self-awareness, healing, and transformation.

We dive into:
•How Carmen bridges ancient astrology with modern trauma therapy
•The surprising origins of astrology in medicine and religion
•Why full birth charts go deeper than horoscopes or memes
•Real stories of healing, intuition, and transformation
•Ethical concerns and scientific research in astrology
•Whether astrology can complement or surpass traditional therapy
•The role of free will vs. destiny in astrological interpretation

If you’re a skeptic, a believer, or just curious—this conversation will challenge you to look at astrology in a whole new light.

⸻

Find Carmen:
Instagram: https://www.instagram.com/carmen_turner_schott_author/
Website: https://carmenturnerschott.com/bio/
YouTube: https://www.youtube.com/ ⁨@CarmenTurnerSchott⁩  

Chapters:
00:00 Skepticism and Curiosity about Astrology
02:56 Personal Experiences and the Journey into Astrology
05:53 Astrology as a Tool for Self-Awareness
09:17 The Science and History of Astrology
12:37 Astrology's Role in Religion and Culture
15:30 Skepticism and Confirmation Bias in Astrology
18:21 Balancing Astrology with a Military Career
21:59 Transitioning to a Full-Time Astrologer
30:01 Astrology and Personal Journey
31:44 Astrology as a Therapeutic Tool
36:06 Research and Ethics in Astrology
37:33 Bridging Astrology and Psychology
46:19 Astrology: Understanding and Responsibility

📺 Listen on your favorite platform:
Spotify/Apple: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 84
Guesting Lachie Colledge

What if the key to living a truly grateful life was hidden in a foreign language—or in a 7-year-old street kid’s smile?

Today’s guest is Lachie Colledge, a medical student who left behind textbooks to travel the world in search of something deeper. From monasteries in Myanmar to roadside reflections in Norway, Lachie’s story is a masterclass in mindfulness, purpose, and finding gratitude in the most unexpected places.

In this conversation, we explore:
 • What “gratitude” really means (and why most of us are doing it wrong)
 • Why a single French word changed Lachie’s life
 • How a moment in India with a street kid flipped his understanding of generosity
 • The link between reconnaissance, gratitude, and ambition
 • Why meditation isn’t just calming—it’s painful, raw, and transformational
 • How to find joy without changing your life—just your awareness

If you’ve ever struggled to balance gratitude with ambition… this episode is for you.

Takeaways:
Gratitude is about being intentional and present.
Decisions can be made through intuition and logic.
Language encodes wisdom and life lessons.
Understanding pain leads to compassion for others.
Meditation helps in self-discovery and clarity.
We are interconnected and dependent on others.
Gratitude can drive ambition and purpose.
Small acts of kindness hold significant value.
Travel teaches profound lessons about generosity.
Our journey is shaped by those who support us.

Chapters:
00:00 Meet Lachie
06:50 The Depth of Gratitude
12:47 Meditation and Self-Discovery
18:14 Understanding Generosity and Community
24:30 Lessons from a Young Boy
32:18 The Duality of Gratitude and Ambition
40:53 Navigating Decision-Making: Heart vs. Logic
47:01 The Courage to Act: Overcoming Hesitation
51:16 Embracing Opportunity: Staying Ready for Change
57:10 Dreams and Aspirations: Paths to Fulfillment

Follow Lachie:
📖 Blog: afrenchworld.substack.com
📸 Instagram: https://www.instagram.com/lachie.colledge/
🧘‍♂️ Read his article on “Reconnaissance”: https://afrenchworld.substack.com/p/reconnaissance

📺 Listen on your favorite platform:
Spotify/Apple: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

I am on a mission to get 100k downloads by August 31st. Help me get there by sharing this podcast.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 83
Solo Episode

In this episode, Jack Wagoner explores the concept of sacrifice and its relationship to fulfillment and success. He reflects on the inherent struggle between ambition and gratitude, sharing personal anecdotes and insights from successful figures like Alex Hormozi. The conversation delves into the challenges of balancing personal desires with the sacrifices required to achieve them, ultimately emphasizing the importance of finding contentment in the present while pursuing future goals.

Takeaways:
We are inherently bad at sacrifice.
Everything has a price, especially time.
Fulfillment is often the finish line we chase.
Success is supposed to bring happiness, but we sacrifice happiness for success.
Some people find satisfaction in simpler lives.
Gratitude helps lessen the pain of sacrifice.
We can't have everything; embracing sacrifices is key.
The duality of gratitude and ambition is ever-shifting.
Finding balance between inward peace and outward success is challenging.
Reflection is essential for growth and understanding. 

Chapters
00:00 The Nature of Sacrifice
02:25 The Pursuit of Fulfillment
05:49 Balancing Gratitude and Ambition
08:30 The Journey of Self-Reflection
11:37 Embracing the Process of Growth


📺 Watch the full episode or listen on your favorite platform:
Spotify/Apple: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 82
Solo Episode

In this episode, Jack Wagoner shares his experiences on his trip out west, reflecting on the beauty of nature and the expectations we set for personal growth during such journeys. He emphasizes the importance of soaking in experiences without the pressure of achieving inner peace or change, advocating for patience and the understanding that personal growth is a gradual process. Jack also discusses the significance of desires and how they can impact our sense of control in life, concluding with a reminder to appreciate the present moment.

Takeaways:
Expecting change from external experiences can be misleading.
Personal growth requires patience and cannot be rushed.
Setting unrealistic goals can limit your experience.
Enjoy experiences for their own sake, not for what they might change within you.
Accumulation of experiences leads to deeper change.
Fictional stories can provide valuable life lessons.
Desires can create a sense of control or victimhood in life.
Letting go of unattainable desires can bring peace.
Gratitude enhances the experience of life.

Chapters:
00:00 Exploring Nature's Beauty
01:54 The Journey Within: Expectations vs. Reality
05:33 Patience in Personal Growth
07:10 Desires and the Control of Life


📺 Watch the full episode or listen on your favorite platform:
Spotify/Apple: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061

Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

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.

⸻

🎯 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

⸻

🌐 Connect with Jon:

🔗 Website: https://jonbassford.com
💼 Consulting: https://think-lateral.com
📲 Instagram: @jon_bassford
📕 Book: The Curious Leader on Amazon: Buy Here

⸻

⏱️ 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

⸻

📺 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.

⸻

🧠 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:
[email protected]

⸻

💬 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

⸻
🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.

Send us Fan Mail

The Grateful Podcast with Jack Wagoner
Episode 80

In this solo episode, Jack Wagoner reflects on his recent experiences while traveling in Boulder, Colorado. He discusses the importance of embracing the journey, being present in the moment, and learning through observation. Jack contrasts the pleasure of expectation with the reality of experiences, emphasizing the need to adapt and find joy in the present rather than clinging to preconceived notions. Through his reflections, he shares insights on personal growth, gratitude, and the beauty of life's unpredictability.

Takeaways:
Go with the flow of whatever happens.
Life has a plan for you.
We have to be open to change and embrace it.
True joy comes from being present.
We learn so much through observation.
Productivity is all about what you're optimizing for.
The pleasure of expectation versus the pleasure of just actually being here.
Ride the wave of life where it's taking you.
This has been the least productive period of my life.
Stay grateful. Love you.


Chapters:
00:00 Embracing Freedom on the Road
02:14 Anticipation vs. Reality
04:51 Learning from Nature
07:48 Redefining Productivity
09:57 Finding Joy in the Unexpected
11:09 Embracing the Flow of Life
14:00 The Power of Presence and Gratitude


Subscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏

⸻

🧠 More from Jack:
Newsletter (Magic, Meaning & Momentum): https://magic.beehiiv.com/v1/aa6b0945-43aa-43c8-b320-0fde6998f852?email=%7B%7Bemail%7D%7D
Instagram: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: [email protected]

💬 If you found this conversation meaningful, send it to a friend and leave a review. It really helps more people find this kind of soul-nourishing content.

⸻

🎙️ 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.

Support the show

InnerVue — a complete self-awareness tool
→ yourinnervue.com
Use code GRATEFUL20 to receive 20% off a Tier 1 InnerVue, along with a complimentary coach-led debrief of your report

☕ Magic Mind — My daily performance shot:
→ https://magicmind.com/wagoner20
Use code WAGONER20 for 20% off a package or 48% off a subscription.

🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: [email protected]
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking.  My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

Subscribe and turn on notifications so you never miss an episode.

Stay grateful, stay hungry.