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/ The Tyler Dickerhoof Show https://www.youtube.com/@impactdrivenleader https://www.instagram.com/thetylerdickerhoofshow/ Subscribe to the newsletter: https://impactdrivenleader.beehiiv.com/ Tyler is on: https://www.tylerdickerhoof.com/ https://www.facebook.com/tyler.dickerhoof.3 https://www.instagram.com/tyler_dickerhoof/ https://www.linkedin.com/in/tyler-dickerhoof-1960351b 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? Learn more about your ad choices. Visit megaphone.fm/adchoices