Why Trying Harder Isn’t Always the Answer
In this solo episode of The Grateful Podcast, Jack Wagoner flips the hustle narrative on its head.
You’re doing everything right. You care more than most. You push harder than anyone you know. So… why isn’t it working?
Enter: The Backwards Law.
Jack dives deep into the paradox that the more we chase success, happiness, peace, or achievement—the more resistance we create. From his days grinding for a baseball dream to launching a top 2.5% podcast, Jack shares why letting go might just be the secret weapon nobody talks about.
This episode explores:
• The truth behind why trying too hard creates failure
• The difference between surrender and giving up
• Why desperation lowers your perceived value
• How to move from panic to peace without losing your ambition
• A practical framework for chasing goals without losing yourself
• A vulnerable look into Jack’s recent internal battles and breakthroughs
Whether you’re chasing success, building a dream, or just trying to breathe again—this episode is your invitation to ease up, trust more, and fall back in love with the process.
Timestamps:
00:00 The Backwards Law: Understanding Resistance
03:08 The Pressure to Succeed: A Personal Reflection
06:34 The Paradox of Patience and Ambition
09:24 Learning from Experience: Wisdom in the Journey
10:56 Gratitude and Growth: A Long-Term Perspective
🎧 The Grateful Podcast with Jack Wagoner
Episode 92 – Recorded in Nova Scotia
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📺 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
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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: https://www.instagram.com/jack_wagoner_/
1:1 Coaching & Dream-Chasing Guidance: jackcwagoner@gmail.com
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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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