The Wake-Up Call Every High Achiever Gets in Midlife

StevenMiyao
3 days ago
4 min read

Episode of Midlife Remix with Larry Olson

Larry, who worked with Nike, Apple, Spike Lee, Al Gore, and others inside the top advertising companies, had three goals. He wanted a national ad campaign, a Times Square takeover, and to win a Gold Pencil, the Oscar of Advertising. He achieved it all within six weeks, and it felt great for a second, only to be replaced by a horrible sinking feeling. This is not what he thought it would be. Where is that feeling of success?

There’s a midlife phase where you’re actively engaged, meeting expectations, but the sense of fulfillment has changed. This occurs because we're midway through life, facing health issues, children’s problems, and aging parents. Typically, it’s a sign that the motivations that once drove you aren’t as strong or relevant anymore.

“We're the architects of our life, you know? And I think the first half of my life, my ego drove me, I needed to achieve these things. And in the second half of my career, I'm saying my soul drives me. I'm listening to my intuition a lot more.” - Larry Olson

That’s the starting point of my conversation with Larry Olson, a creative leader who built a career at the very top of his field and then found himself questioning everything he thought success meant.

The Breaking Point

Larry’s midlife unraveling began in a doctor’s office with a diagnosis of MS, continued at home as his daughter fell into a deep depression, and worsened when his thirty-year marriage ended, followed shortly by his father’s passing. All of it happened in a quick span. The man who once navigated deadlines, expectations, and pressure with ease suddenly found himself without anything stable to depend on.

In the episode, Larry talks openly about how this series of blows forced him to stop and confront the question many midlife professionals eventually face quietly: Who am I now that the life I built no longer looks the same?

The Turn: From Ego to Intuition

Larry is candid about his early career.

“It was brute effort,” he said. “If it wasn’t painful, I didn’t think I earned it.”

His identity was tied to output, and output came from force. But after that Times Square moment, something in him started to question the path. He wrote three simple things on a Post-it note:

live in the mountains
work on something meaningful
be around inspiring people

He didn’t have a plan for getting there. He just knew the old ways were no longer the right ones. A few weeks later, an unexpected email arrived pulling him into climate work with Alex Bogusky and Al Gore.

“I didn’t know how any of it would happen,” he said. “But it happened almost immediately once I named it.”

Many midlife professionals arrive at a similar moment when the ladder they’ve been climbing no longer aligns with the life they desire.

The Hard Reset

After relocating, life didn’t become easier; it became more authentic. A series of losses eroded nearly every identity he had relied on. He described it as being “taken down to the studs.” Over time, the resistance eased, and something shifted.

“It burned away the unnecessary parts of me,” he said. “I came out lighter, clearer, more myself.”

Midlife often works this way behind the scenes. It’s not a dramatic crisis; it’s a forced reckoning with what’s true and what’s no longer sustainable.

The Work of Knowing Yourself

As Larry went through rebuilding, he started investing in something he had often avoided earlier in his career: understanding himself. He told me,

“The most important thing you can do in your career is get to know yourself. The relationship you have with your thoughts, the relationship you have with your mind — that’s the most important investment you can make.”

This wasn’t just abstract advice for him; it was about survival. He needed to understand how his mind functioned under pressure, what stories he told himself, which patterns stemmed from fear, and which instincts arose from a deeper place. I often see this in my coaching work — once the external structure is gone, people realize how little attention they’ve paid to their internal one. Midlife calls for that shift. It demands a different kind of awareness and a more honest relationship with oneself.

Midlife’s Patterns

Larry’s story is unique, but the pattern shows up in many people in midlife. Careers shift, families change, health issues surface, and the identities that once felt solid start to move. It can be disorienting, but it also creates a clearer view of what’s happening beneath the surface. What Larry discovered and what I see often in my work is that once the familiar structures fall away, people start making choices based on who they are now, not who they were years ago. It’s the point where you begin to rebuild your life in a way that supports the person you’ve become.

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