In this episode of The Tyler Dickerhoof Show, Tyler Dickerhoof welcomes former Nike executive and author of Worthy Wins: Pointing Your Life Toward What Matters Most, John Olinger, for a powerful conversation on purpose, loss, and redefining success.

As Nike’s Global Brand Director for Kobe Bryant, John led one of the most emotional campaigns in the company’s history following Kobe’s tragic death. But behind the dream job and high-level wins was a deeper tension—between achievement and alignment, performance and people, career and calling.

John opens up about what Kobe’s legacy taught him, why most leaders are chasing empty goals, and how personal tragedy forced him to reassess everything. From boardrooms to burnout, he shares how ambition can quietly wreck relationships—and how small, consistent actions can build a life that actually matters.

Together, they unpack the cost of climbing the wrong ladder, the trap of tying identity to success, and the power of taking a pause before it’s too late. If you're feeling stretched, stuck, or unsure what really counts—this conversation is a reset.

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What We Discussed:

00:00 Introduction

01:25 Why the dream job isn’t always the dream

03:18 How a tribute to Kobe became a life-altering moment

07:53 Climbing the right ladder starts with the right building

13:42 What Kobe’s post-NBA life revealed about true wins

18:27 The true cost of chasing the wrong wins

21:39 If it’s worth it, it’s worthy

25:04 How to know when it’s time to leave a great job

29:38 What makes someone a great leader?

35:39 How personal struggles affect workplace performance

38:24 Two ways personal chaos shows up at work

43:40 What do you want your corporate obituary to say?

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