From Fear to Alignment: Redefining Success, Leadership, and the Self

StevenMiyao
Sep 2
3 min read

“I was afraid the whole thing would collapse. That I’d have to tell the people who trusted me that I lost their money. I was under pressure. And I wasn’t showing up as a good husband… or a good father.” - Jack Swift

Jack Swift doesn’t open our podcast conversation with stories of selling billion-dollar companies or his time as an Army Ranger—he begins with a personal inflection point that reshaped how he lives, leads, and defines success.

In my work coaching leaders, particularly those in midlife navigating high-stakes decisions, I’ve seen how these important, internal battles often shape us far more than the accolades or outcomes we’re known for. Fear, misalignment, and self-doubt affect everyone, even those who are highly accomplished.

What Fear Really Teaches Us

Jack has built and exited multiple high-growth companies. However, in this conversation, he shares how his most transformative lessons came not from achievement, but from fear.

The kind of fear that hijacks your nervous system. It keeps you trapped in late-night cycles of uncertainty and fear. Not fear of external threats, but fear of internal collapse: Fear of failure. Fear of judgment. Fear of success.

Jack shared a powerful framework for facing fear: He identifies which “bucket” the fear belongs to, then asks why. Not once, but several times, until the root becomes clear. This isn’t just emotional processing. It’s leadership training.

“Once it’s approachable, I can ask: what is the learning here?”“Thank you, fear. You’ve helped me return to what matters.”

Alignment Over Achievement

After years of external success, Jack began making decisions others couldn’t understand, from walking away from a prestigious role at Janus Henderson to leaving an earnout on the table after growing Tiffin to nearly a billion-dollar valuation.

Why?

Because his heart wasn’t in it.

“When my head and heart are aligned, I feel joy. When they’re not, I don’t.”

Instead of pursuing titles, he began to listen for what was motivating him, even if it didn’t make sense on paper. This change didn’t mean giving up ambition; it meant grounding it in purpose.

Redefining “Work Hard” and Finding Flow

As we talked about work, Jack offered a more human (and frankly, more sustainable) lens on productivity: rhythm.

He described how tuning into daily, seasonal, and even energetic rhythms has helped him know when to push and when to pause, working with the body rather than against it.

“Sometimes the most productive thing I can do is go for a hike. I’ve learned to trust that.”

Leadership in the Age of AI

With AI reshaping nearly every industry, we explored what it means to lead in a world where machines can out-think and out-optimize us.

Jack’s take? The value of being human is rising.

“AI can process information. But it can’t sense, it can’t imagine, it can’t feel.”

In a world where logic is outsourced to machines, intuition, creativity, and emotional intelligence become our most vital skills. Leadership today is not merely about making decisions; it is about having the ability to discern and understand the best path forward.

The Path Forward: Listening, Not Controlling

What I appreciated most about this conversation was its honesty. Jack didn’t present his journey as a clean progression. He acknowledged the moments when he ignored his instincts and the consequences of remaining misaligned for too long.

And he also shared the incredible possibilities that opened up when he did.

This isn’t just about personal growth. It’s about preparing ourselves and others for a future that demands a deeper kind of leadership.

“You don’t need all the money or titles to be secure. You’re already held. The moment you realize that, you’re free to follow your heart.”

Want the full story? Hear the complete conversation with Jack Swift, including real-world examples, lessons learned, and practical tips to impact on your career and life: YouTube, Spotify, Apple Podcast, Substack

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