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The Learning Leader Show With Ryan Hawk

The Learning Leader Show With Ryan Hawk

Written by: Ryan Hawk
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 As Kobe Bryant once said, "There is power in understanding the journey of others to help create your own." That's why the Learning Leader Show exists—to understand the journeys of other leaders so that we can better understand our own. This show is full of learnings taught by world-class leaders—personal stories of successes, failures, and lessons learned along the way. Our guests come from diverse backgrounds—CEOs of multi-billion dollar companies, best-selling authors, Navy SEALs, and professional athletes. My role in this endeavor is to talk to the most thoughtful, accomplished, and intentional leaders in the world so that we can learn from them as we each create our own journeys.Learning Leader LLC 062554 Careers Economics Management Management & Leadership Personal Success
Episodes
  • 687: Jim Collins - What To Make of a Life, The 3 Types of Luck, Inflection Points, Cliffs, Encodings, Navigating the Fog, the Art of Getting People To Want To Do What Must Be Done, and Reconnecting with an Old Friend

    687: Jim Collins - What To Make of a Life, The 3 Types of Luck, Inflection Points, Cliffs, Encodings, Navigating the Fog, the Art of Getting People To Want To Do What Must Be Done, and Reconnecting with an Old Friend
    May 10 2026
    NEW BOOK -- The Price of Becoming Buy it -- www.LearningLeader.com/Becoming The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. Jim Collins is the author of some of the most influential business books ever written — Good to Great, Built to Last, and Great by Choice. His concepts have become part of the leadership vocabulary. Level 5 Leadership. The Flywheel. First Who, Then What. The Hedgehog Concept. He spent more than a decade at Stanford as a professor and has advised CEOs, four-star generals, and heads of state. His new book is What to Make of a Life: Cliffs, Fog, Fire, and the Self-Knowledge Imperative. It is the product of ten years of research and is the most personal thing he has ever written. We flew to Boulder, Colorado, to record this one in person with Jim. Key Learnings Jim's grandfather wrote his own death story. Jimmy Collins was a test pilot in the 1930s. He told Jim's grandmother, Dolores, that if he died, she should pull the last chapter from his desk and publish it. He died in a test crash. After the service, she pulled out the chapter. The title was "I'm Dead." The last chapter, written in first person, described the plane coming out of the sky, the screaming wings, the crash. The final words, by his own pen: "I am dead now." For seven decades, his grandmother never cried. When Jim asked her in her nineties to tell the story of his grandfather, she cried and said, "Thank you for that. I've never cried before." She'd been a single mom in the middle of the Depression. Of all the things Jim feels good about in his life, asking her to tell that story before she died at almost 100 years old is one he's most proud of. A cliff is an event that alters the trajectory of your life and forces you to reconstruct everything that comes after. Jim's first big cliff: he lost his father while his father was still alive. Jim's father took the family to San Francisco in the 1960s. They lived a few houses down from Haight Street. When a man was shot dead on their doorstep, Jim's mom moved them to Boulder. They lived in a cold basement with cots and a hot plate. They couldn't afford a Christmas tree, so Jim and his brother rolled a boulder into the basement and called it their Christmas rock. The Greyhound bus moment. In high school, Jim took a Thanksgiving turkey on a Greyhound bus down to New Mexico, where his father was living in an adobe hut with a dirt floor. He had this romantic vision: they'd cook the turkey, share Thanksgiving, bond as father and son. The whole weekend, his father had no interest in him. He spent it trying to convince Jim to convince his grandmother to give him money. On the bus ride home, looking out the window into the fog, Jim realized: there will never, ever be a father there. No male role models. No frameworks. No guidance. "I've got this one life. What do I do with it?" The inflection point in Jim's life is Joanne. They got engaged four days after their first date. He'd admired her from afar for years but never had the courage to ask her out. Once they were together, Jim began a conscious process: I need to become a person worthy of being married to her. He didn't know exactly what that meant or how to get there. But he knew that was the work. Forty-six years later, it's still a never-ending journey. What Joanne does brilliantly: she sees what needs attention. Jim is encoded to hear it. Someone once asked Joanne what she thought Jim's greatest strength was. She said: "Jim takes critical feedback better than any person I've ever met." Joanne sees what needs attention. Jim hears it. Then they adapt and adjust. That's the inner flywheel of their marriage. Circle the wagons together. Guns pointing out, never at each other. When life gets really difficult, whether it's disease or other cliffs. You are always together. Always on the inside of the wagons. Never aimed at each other. Joanne won the 1985 Hawaii Ironman by 92 seconds. With a hamstring injury that limited her running training to 16 miles a week, she came off the bike with a 10-minute lead. Then mile by mile, the lead shrank. Nine minutes. Eight. Seven. With a few miles left, she stopped in the middle of the lava field, massaging her legs, almost pleading with them to run. She looked up at the sky. Then her gaze fixed somewhere down the road. She started to run. You're racing for self-respect. Joanne told Jim afterward: in the end, you're racing to know that you couldn't have run a step faster. Only you'll know. If you know you couldn't have run a step faster, that's actually winning. When Jim writes, he's on the lava fields. When he finishes a book, he wants to know he couldn't have written one sentence better. When you're on the lava fields, this is the moment you want to quit....
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    1 hr and 44 mins
  • 686: Dr. Nicole LePera (The Holistic Psychologist) - The Hidden Cost of Being Good at Everything, Self-Medicating at 13, Why Awareness Isn't Enough, Healing the Body Not Just the Mind, What a Real Boundary Actually Is, and How Vulnerability Makes Love Rea

    686: Dr. Nicole LePera (The Holistic Psychologist) - The Hidden Cost of Being Good at Everything, Self-Medicating at 13, Why Awareness Isn't Enough, Healing the Body Not Just the Mind, What a Real Boundary Actually Is, and How Vulnerability Makes Love Rea
    May 3 2026
    Pre-Order new book, The Price of Becoming www.LearningLeader.com/Becoming This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver My Guest: Dr. Nicole LePera is the creator of The Holistic Psychologist, a platform with over 12 million followers, and the author of three New York Times bestselling books, including her newest, Reparenting the Inner Child. Key Learnings: Nicole was good at everything, so struggling meant failure. Her family's message was clear: success in life meant financial security through academics or athletics. The implicit message: you're worthy when you're bringing home A's, when you're winning the softball game. She quickly learned to identify things she wasn't immediately good at and just not pursue them. She filtered life, staying on the path of comfort. Your childhood adaptations don't leave. Nicole calls it the inner child. It doesn't matter how old you are or how far beyond your childhood you think you've gotten. It impacts you in reactions, in identities, in your way of being. What was once your best attempt at safety, security, or connection still drives behavior today. Not all adaptations are problems. Many continue to benefit us. The question isn't whether the adaptation is good or bad. The question is: are you choosing it, or is it choosing you? Nicole's drive for achievement created opportunities. It led to massive impact. But she still has the overachiever who wants to blow past her limits and say yes when she's exhausted but means no. The Holistic Psychologist started in 2018, and Nicole had no idea it would explode. She was living in Philadelphia, operating within a private practice model. Within the first year, people from around the world were resonating, joining, and interested in working with her in this new way. But at the beginning, even learning how to speak on camera was such a big challenge. Her partner would say, "Say what you said to me earlier," and Nicole's mind would go blank. Just putting a camera in front of her was near debilitating. Boundaries are about knowing who and when to take feedback from. Sometimes the feedback from a loved one, while uncomfortable, is helpful to hear. Other times, it's a helpful boundary where you're not opening yourself up to the opinion of someone who has a different vantage point or is speaking from their own projection. That's allowed Nicole to create safety in herself, confidence in herself, which translates to flow. Several years in, Nicole's dad sat front row at her book event, crying with pride. In the beginning, her dad and mom would ask, "Why do you have to use us as the example? Why do you have to share about our family?" Nicole would explain: " This is the only experience I can speak from, and our family's experience is so common. To see her dad, who came from a family largely shut down emotionally, crying in understanding and pride, was overwhelming and validating for why she does this work. At 13, Nicole was getting straight A's but unraveling on the inside. She was socially shy, struggled to order food at restaurants, and had very few friends. Then she discovered alcohol and pot made her feel comfortable. That anxiety she lived with suddenly felt freer. She would stumble through the living room at night, her parents already in bed, then wake up at 6:00 AM the next day, pitch a softball tournament, win it, and seemingly be fine. Her parents had no idea. She was very good at suppressing her emotions and coping. By contrast, on the surface, it seemed like she was doing well. They were a family who didn't really talk about emotions, so they had no indication. The drive itself isn't the problem. It's the energy that inspires action. Nicole's dad worked into the night to support the family. Her mom would say, "why not 100?" when Nicole brought home a 96. That translated into drive and ambition. That's not a problem. For a lot of us, it's the energy that inspires action and translates into impact. It can become a problem when we have no limits to our working, where we exhaust ourselves and burn out, where we don't feel worthy in moments of inaction or rest. The marker of a healthy relationship with drive is flexibility. When you're forced to stop because you're sick, exhausted, emotionally overwhelmed, or someone else needs you, can you be flexible enough to do that without feeling terrible about yourself? The ability to choose to say, "Okay, contextually speaking, I need to pause," and still feel okay about yourself, that's the marker. Hold space for both: acknowledging harm and taking agency. Other people have contributed to our discomfort. Maybe parents didn't meet our needs. If we don't acknowledge that, we suppress. But we also can't stay stuck in anger and resentment. A true boundary isn't demanding that ...
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    1 hr and 1 min
  • 685: David Epstein - The Freedom Trap, Narrative Values, General Magic, The Nobel Prize Winner Who Simplified Everything, Wearing the Same Thing Everyday, and Why Constraints Are the Secret to Your Best Work

    685: David Epstein - The Freedom Trap, Narrative Values, General Magic, The Nobel Prize Winner Who Simplified Everything, Wearing the Same Thing Everyday, and Why Constraints Are the Secret to Your Best Work
    Apr 26 2026
    Read my new book, The Price of Becoming. www.LearningLeader.com/Becoming The Learning Leader Show with Ryan Hawk This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My guest: David Epstein is the #1 New York Times bestselling author of Range and The Sports Gene. A former investigative reporter at ProPublica and senior writer at Sports Illustrated. His new book is called Inside the Box: How Constraints Make Us Better. Notes Be part of "Mindful Monday" -- Text Hawk to 66866 Key Learnings The easier move is to let it go. David found a factual error in Ryan's new/my new book. David was supposed to read it and write a blurb on it - but went further and challenged a factual error. The kind move, what great leaders actually do, is being willing to point things out, even if it could cause a little friction. There is such a thing as too much autonomy. After Range became mega viral, David optimized for autonomy. He individualized his whole life. He no longer was writing about what others assigned him. A year later, he realized there is a thing as too much autonomy. He missed the structure of a work day, the deadlines, the annoyances of working with other people's schedules. This total freedom ended up feeling terrible. "The great thing about being committed by your own choice is that you can stop wondering how to live and start living." This quote by Mihaly Csikszentmihalyi hit David when he was on a dating app for book topics, just swiping and swiping. That day he said, "I'm really interested in constraints. I need some myself. I'm writing a book proposal on this." Two weeks later he was 10 times more interested because he decided to dive into it. Cal Newport says "system shutting down" at the end of his workday. It seems silly, but when you have all that freedom, you need something to close the workday so you can recover and be ready for the next day. Your brain is made for preventing you from having to think whenever possible. Cognitive scientist Daniel Willingham says thinking is energetically costly. So when your calendar is too open, all you'll do is what's convenient. Your brain will be lazy. The path of least resistance. The mere urgency effect: when schedule and structure is too open, people do things that seem urgent even if they're unimportant. When you're too unstructured, you end up doing huge volumes of low value stuff just to have checked off doing something. What David's workday looks like now: Batching work: people at work check their email on average 77 times a day. The way people are usually doing that is they're toggling all the time between email and something else. When you do that, it lowers your productivity and massively increases your stress.David doesn't start his day with his inbox. He'll check it at the end of the workday because emails can take him away from the most important work at the beginning of the day. Stress + Rest = Growth. The workday ends when David's son gets home. When writing, you have to program in rest, just like you would if you were an athlete in training. Daniel Kahneman said writing "Thinking Fast and Slow" was the worst few years of his life. David had lunch with Kahneman and praised the book. Kahneman said, "Never again." He said it was so isolating. He was used to working with a partner or multiple partners and colleagues. He felt so isolated that he said he'd never write a book again, or if he did, he would write it with somebody else. And that's what he did. And David could empathize with that. David made a one-page architectural outline for how "Inside the Box" would look. If it's not on that page, it is not in the book. He wrote as small as possible to try to defeat his own system. The book's 20% shorter than his other two. He thinks it's much tighter writing. He was so much more efficient that he doesn't feel nearly as burned out. After a mega hit book, two things matter: (1) A lot is out of your control, and (2) Identify as a craftsman. David's colleague at Sports Illustrated told him, "If a book about genetics and vampires comes out the same day, you're screwed, and there's nothing you can do about it." He was right. But David very strongly identifies as a writer now, as a craftsman. He's taken fiction writing courses just to learn about craft. With Inside the Box, he did a structural experiment that he found so engaging because he was focused on the craft itself, not just the commercial outcome. "Docendo discimus" - by teaching, we learn. This is a quote from Seneca. If people think they're going to have to teach certain material, they organize it more coherently in their own mind. They start pulling out main ideas and attaching different ideas together. Teaching it is even better, but just making someone think they're going to have to ...
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    57 mins
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