EP. 33 - Things I’ve Changed My Mind About — Success

In this episode:

  • Why external success can hide an unhealthy life.

  • The startup story that completely reframed my thinking about ambition.

  • What building SwiftReporter continues to teach me about stress and presence.

  • The moment my daughter pulled me away from my phone—and why it still stays with me.

  • What paddling the Hunter River taught me about struggle, patience, and control.

  • The simple life lesson my grandfather ("Pop") shared that has become more valuable every year.

  • Why we've confused exhaustion with progress.

  • The difference between hard days and hard lives.

  • A quieter, broader definition of success.

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EP. 32 - The Stories We Never Question
  • The Toddler’s Focus: Why children are born with a relentless curiosity that adults eventually trade for rigid self-defense.

  • Lessons from the Monastery: How stripping away modern complexity, technology, and constant chatter exposes the rules we never consciously chose.

  • The Cuban Paradox: Breaking the illusion that great output requires sacrificing deep presence with family and friends.

  • Unpacking the Startup Hustle: Challenging the toxic badge of honor that demands leaders become completely unavailable for their own lives.

  • What the River Teaches: Moving from an obsession with aggressive control to a deeper, nature-aligned definition of structural progress.

  • Fatherhood as the Ultimate Pattern Interrupt: How children inherently refuse to measure our worth by résumés, titles, or income.

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EP. 31 - What Does a Good Life Actually Look Like?

We have become incredibly good at measuring the quantity of our achievements: revenue, follower counts, equity, and scale. But somewhere along the way, those metrics quietly became a substitute for a much deeper conversation.

In this episode, we step back from the modern obsession with productivity and ask a much older question: What does a good life actually look like?

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EP. 30 - The Stories We Carry: Why Your Detours Are Never Wasted Time

We spend an enormous amount of energy regretting the chapters of our lives that didn’t go exactly according to plan. The failed projects, abandoned career paths, and strange detours often feel like a massive lack of focus. We punish ourselves for not moving in a straight line.

But what if you weren't distracted? What if you were just collecting the ingredients for the exact thing you were always meant to build?

In this episode, Evan breaks down why a seemingly "scattered" past is actually a massive structural advantage. Drawing on his own disconnected chapters—from living in a Buddhist monastery and teaching in a Brazilian favela, to paddling 470km down a drying river and building a B2B tech startup—he explains how to view your history not as a series of failures, but as pure Research and Development.

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EP. 29 - Building Things That Matter (The Messy Middle)

In this episode, we cover:

  • The Danger of Beginnings: Why constantly chasing the "spark" of new ideas is just another version of the pleasure trap.

  • The Hunter River Metaphor: Why the obstacles in your path aren't stopping the journey—they are the journey.

  • The Illusion of the Finished Product: Why comparing your unfinished reality to someone else’s polished success is destroying your peace of mind.

  • Redefining the Reward: Why aliveness isn't a prize waiting at the finish line, but a skill you cultivate while things are still completely unfinished.

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EP. 27 - The Most Dangerous Phrase in Life

What if the thing holding us back isn't failure?

What if it's the constant feeling that we should already be further ahead?

After paddling 470km down the Hunter River, Evan Sutter found himself repeatedly confronting the same thought:

"I should be further ahead by now."

Further down the river.

Further in business.

Further in life.

Further towards the person he thought he was supposed to become.

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EP. 26 - You Can't Rush A River

A few years ago, I paddled 470 kilometres down the Hunter River from its source in the Barrington Tops to the ocean at Newcastle.

I thought the challenge would be physical.

Instead, it became a lesson in patience.

Along the way I battled wind, tide, shallow water and the constant feeling that I should be further ahead than I was. The harder I tried to force progress, the more frustrated I became.

What the river taught me is something I've since encountered while building businesses, raising a daughter, studying psychology and pursuing meaningful goals:

You can't rush a river.

In this episode, I explore what the Hunter River taught me about patience, adaptation, expectations and why many of the things that matter most in life simply refuse to operate on our preferred timeline.

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