I Have Some Questions...

077: "Performing and Leading Are Entirely Different Sports" ft. Michael Bostarr

• Erik Berglund

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0:00 | 1:28:25

In this candid and energizing conversation, Erik sits down with Michael Bostarr — a coach, creative, and former sales leader who made a bold pivot from performance-driven achievement to values-based leadership. Together, they explore how to shift from chasing external validation to living and leading with clarity. Michael shares the real story behind walking away from big roles, the surprising weight of “almost” success, and what happens when you build your identity from the inside out. Whether you’re mid-career, mid-pivot, or just feeling the grind, this episode is a permission slip to do things differently.

👤 About the Guest

Michael Bostarr is a leadership coach, poet, and former sales leader with a talent for helping high-performers turn inward to unlock deeper clarity and meaning. His path has spanned sales leadership at early-stage startups, coaching work that centers wholeness and humanity, and creative expression that invites others to slow down and pay attention. He brings the rare ability to pair deep introspection with grounded business experience — and isn’t afraid to challenge hustle culture while still pursuing excellence.

🧭 Conversation Highlights

  • What it really feels like to "almost" make it — and why it can be more painful than failure
  • The mental gymnastics of being in the top 10% but feeling like you're underperforming
  • Why "performer energy" breaks down in leadership — and what to do instead
  • Michael’s moment of clarity: leaving a prestigious job without the next step lined up
  • Why identity work is central to sustained success — and how Michael helps clients do it
  • The difference between leading from essence vs. leading for optics
  • Why poets and entrepreneurs have more in common than you'd think

💡 Key Takeaways

  • Performing and leading are different sports. You can’t outwork your way to leadership presence.
  • The pain of “almost” can keep you stuck longer than failure. Until you get honest, it lingers.
  • Identity clarity is underrated. When you know who you are, you stop needing every win to prove it.
  • Letting go of the plan creates space for what actually wants to emerge. But that’s terrifying.
  • Coaching isn’t about having answers — it’s about expanding the questions.

❓ Questions That Mattered

  • “When did you realize the cost of performing had gotten too high?”
  • “What’s the difference between coaching someone’s role and coaching someone’s soul?”
  • “How do we lead when we’re still in the fog?”
  • “What did it feel like to step away from something everyone else wanted?”
  • “Where do you notice people outsourcing their clarity?”

🗣️ Notable Quotes

“Being 95% of the way to your goal can be more brutal than failing.”

“There’s a moment in every leader’s journey where they realize performing no longer works.”

“I realized I was playing a game I didn’t even want to win.”

“I’ve coached founders, artists, sales leaders… The thread is always the same: they want to be more themselves.”

“Sometimes the scariest leadership move is choosing not to fill the space with answers.”

🔗 Links & Resources