Kyle Thiermann — Deadlines, Mentors, Curiosity, and the Craft of Connection (#95)

Kyle Thiermann — Deadlines, Mentors, Curiosity, and the Craft of Connection (#95)

1:17:11 Nov 18, 2025
About this episode
About KyleKyle Thiermann is a professional big-wave surfer, journalist, and creative director whose career bridges storytelling, advertising, and adventure. He’s written for Men’s Health, Surfer, and Outside Magazine, and helped shape campaigns for brands like Patagonia, Yeti, and Mudwater, with his ads and viral spots reaching over 100 million people. Kyle is also the author of One Last Question Before You Go: Why You Should Interview Your Parents Now, a deeply personal exploration of family, curiosity, and conversation. In this episode, Justin and Kyle dive into the fear that drives creativity, the lessons of surfing six-story waves, and how to use curiosity and courage to build a more meaningful creative life.Think Like A Game Designer is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Ah-ha! Justin’s TakeawaysDeadlines create gravity: Surrounding yourself with people you respect and setting clear deadlines are two of the most powerful tools for getting things done—it is the engine of creative work, which turn ambition into action and ensure you finish what you start. Proximity is an accelerant: Kyle’s learned, both in the ocean and in his creative career, that the fastest way to improve is to surround yourself with people already doing the thing you’re learning. Mentorship and shared goals create a rhythm of steady progress that’s hard to find alone.Better questions equal better understanding: We’re trained to have answers, but not to ask better questions and that’s where understanding truly lives. Whether you’re exploring a design challenge or rebuilding a relationship curiosity has the power to turn conversation into insight. Kyle’s book about interviewing his parents is a masterclass in curiosity.Show Notes“The power of deadlines and more specifically, the fear of disappointing people I respect has driven my career.” (00:04:55)We start by talking about the writing group where Kyle and I met, guided by New York Times best-selling author Neil Strauss. Together we dig into how essential structure and accountability are for any creative project including the value of mentors, peers, and most of all, deadlines. If you’ve listened to this podcast before, you’ve heard me say it: deadlines are magic. They turn vague ambition into finished work.“Find the people that are doing the thing and hang out with them as much as possible.” (00:15:58)Kyle connects his life as a big-wave surfer to his creative process, showing that fear and mastery follow the same pattern. Whether you’re paddling into six-story wa
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