Jim Olson, Chief Communications Officer: How to Turn your Setback Story into your Comeback Legacy episode artwork

EPISODE · Jul 30, 2026 · 48 MIN

Jim Olson, Chief Communications Officer: How to Turn your Setback Story into your Comeback Legacy

from Stumbling Blocks: How Great Leaders Are Made · host Jonathan Block

Most crisis experts have never actually sat in the room when everything fell apart. Jim Olson has. He was head of communications at US Airways when Flight 1549 landed on the Hudson. He was at Starbucks when its flagship store in Jakarta was bombed. And he was at United Airlines the night Dr. David Dao was dragged off a plane and it became one of the first viral crises in business history.Then the crisis came for him. In 2024 Jim was diagnosed with stage 4 melanoma that had spread to his lung and his brain. During treatment he lost his eyesight. He is now legally blind. And he wrote a book about all of it called Tailwind.We talk about the 2am back pain that had no medical explanation and ended up saving his life. The "do hard things" tattoo he got a month before he went blind. And why he now prays in gratitude for the healing that's already happening instead of begging for the healing he wants.If you're carrying something heavy right now, this one is for you.In this episode:00:00 The monster storm none of us escapes00:25 Welcome to the Treehouse02:00 The Dr. David Dao crisis, from the comms chief's chair06:00 The fog of war, and why the first information is almost always wrong10:54 Inside the Good Morning America apology13:00 When your policies get in the way of your values14:30 Miracle on the Hudson and the three flight attendants nobody named18:36 The unsung heroes in Jim's own life20:53 The 2am back pain that saved his life25:00 Stage 4, and then the brain tumor29:00 Losing his sight33:30 "Cancer made me stronger. Blindness made my world brighter."35:00 Writing Tailwind blind, on short-term disability38:49 Ambition without purpose is a sailboat without a compass41:00 Why me? Oscar Munoz and the two kinds of patients44:49 Faith, gratitude, and a letter to God47:37 Praying for what's already being madeGet Jim's book, Tailwind: https://www.amazon.com/Tailwind-Compass-Turning-Setback-Comeback/dp/B0GXCCZ1QYHear the Oscar Munoz episode referenced throughout: https://podcasts.apple.com/us/podcast/oscar-munoz-ceo-united-airlines-why-its-never-too-late/id1849573843?i=1000744337146Stumbling Blocks explores the stumbles, crises, and formative moments that forge great leaders. Hosted by Jonathan Block and recorded at the Treehouse Studio.Questions? Comments? Email me: [email protected]

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