Join Tyler Dickerhoof as he takes you beyond the headlines, unpacking the biggest stories in news and politics through the lens of leadership. From power shifts and policy decisions to cultural moments shaping our world, Tyler delivers insightful analysis, thought-provoking discussions, and actionable leadership strategies. Discover compelling stories, in-depth interviews with thought leaders, and bold takes that empower you to lead and think critically in today’s ever-changing landscape. Whether you’re a seasoned leader or aspiring to make an impact, this podcast is your guide to understanding the intersection of leadership, news, and the issues that matter most.
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Join Tyler Dickerhoof as he takes you beyond the headlines, unpacking the biggest stories in news and politics through the lens of leadership. From power shifts and policy decisions to cultural moments shaping our world, Tyler delivers insightful analysis, thought-provoking discussions, and actionable leadership strategies. Discover compelling stories, in-depth interviews with thought leaders, and bold takes that empower you to lead and think critically in today’s ever-changing landscape. Whether you’re a seasoned leader or aspiring to make an impact, this podcast is your guide to understanding the intersection of leadership, news, and the issues that matter most.
EP207 - Ex-Nike Director Exposes the High Cost of ‘Winning’
The Tyler Dickerhoof Show
47 minutes
4 months ago
EP207 - Ex-Nike Director Exposes the High Cost of ‘Winning’
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.
Follow John:
https://www.instagram.com/johnolinger/
https://www.john-olinger.com/
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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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The Tyler Dickerhoof Show
Join Tyler Dickerhoof as he takes you beyond the headlines, unpacking the biggest stories in news and politics through the lens of leadership. From power shifts and policy decisions to cultural moments shaping our world, Tyler delivers insightful analysis, thought-provoking discussions, and actionable leadership strategies. Discover compelling stories, in-depth interviews with thought leaders, and bold takes that empower you to lead and think critically in today’s ever-changing landscape. Whether you’re a seasoned leader or aspiring to make an impact, this podcast is your guide to understanding the intersection of leadership, news, and the issues that matter most.
