Mark: Alright Michelle, I'm going to say a name: Michael Jordan. What's the first thing that comes to mind? Michelle: Winning. Six rings. The GOAT. The guy who never lost. Mark: Exactly. Now, what if I told you the secret to his success, and maybe ours, isn't the winning... but the experience of getting cut from his high school varsity team? Michelle: Huh. That’s the classic origin story, right? The failure that fuels the legend. But we always focus on the comeback, not the failure itself. Mark: That is precisely the point. We love the comeback story, but we're terrified of the part that makes it possible. Our book today argues we have it all backward. We shouldn't just learn from failure; we should actively run towards it. Michelle: Run towards it? That sounds like a recipe for a very short, very unsuccessful career. Mark: It sounds completely counterintuitive, but that’s the provocative idea at the heart of Chasing Failure by Ryan Leak. And Leak isn't just some philosopher in an ivory tower; this is a guy who became a USA Today bestselling author and now coaches leaders at Fortune 500 companies and pro sports teams, all based on this one powerful, slightly crazy idea. Michelle: Okay, a leadership coach who tells people to fail. You have my attention. Where does this even begin?

Mark: It begins with a question Leak asks, but he flips the classic script. We've all heard the prompt, "What would you do if you knew you couldn’t fail?" Michelle: Right, it’s meant to unlock your hidden ambitions. Mark: Leak’s version is more daring. He essentially asks, "What dream is so important that you're willing to fail publicly while trying to achieve it?" And he didn't just ask it; he lived it. At 28 years old, long past the prime age for a basketball prospect, he decided he was going to try and make it into the NBA. Michelle: Hold on. At 28? With no college career or draft history? That’s not chasing failure, that’s just... delusional. Mark: It feels that way, doesn't it? He knew the odds were astronomically against him. There was a statistic he found that an American male between 6'6" and 6'8" has a 0.07% chance of making it to the NBA. Leak was 6'3". So, what does he do? He starts training, and then he sits down and emails all thirty NBA teams, asking for a tryout. Michelle: He emailed every single team? That alone is a masterclass in embracing rejection. I can just imagine the responses... or lack thereof. Mark: He got a few polite "no's." The Boston Celtics, the Clippers. But then, something unexpected happened. The Phoenix Suns replied. They said yes. They invited him to come to Phoenix for a workout with their head coach. Michelle: No way. They actually said yes? What happened when he got there? Mark: He flew to Phoenix with a friend to film the whole thing for a documentary. He gets on the court, and he's surrounded by these elite athletes. He participates in a few drills, holds his own okay. But then comes the moment of truth. The coach puts him through a three-minute full-court sprinting drill. It’s designed to separate the pros from the pretenders. Michelle: Oh, I'm getting secondhand anxiety just thinking about this. This sounds like my worst gym-class nightmare, but on a professional stage. Mark: It was brutal. He described how within seconds, the professional players were just gliding, and he was gasping for air, his lungs on fire, his legs turning to cement. He completely and utterly failed the drill. It was the undeniable, physical proof that he did not belong there. He wasn't going to be an NBA player. Michelle: Wow. So he goes through all that, the emails, the training, the public tryout... just to confirm what he probably already knew? What was the point of that public humiliation? Mark: That's the million-dollar question. The point wasn't to make the team. The point was to chase the dream. By running headfirst into the thing he was most likely to fail at, he discovered something profound. He documented the journey, and that documentary, Chasing Failure, opened up a whole new world for him. It led to speaking engagements, and eventually, to a career in leadership development and executive coaching, working with NBA teams from the outside. Michelle: Ah, so the failure wasn't the end of the story. It was the beginning of a different, better story. Mark: Exactly. He has this incredible quote about it: "Chasing failure took me further than chasing success ever did." He didn't get his original dream, but by pursuing it to its breaking point, he found his true calling. He discovered he was better at developing leaders than he was at basketball. The failure was a process of elimination that led him to his purpose. Michelle: That’s a powerful reframe. It’s not about the outcome, it’s about the data you collect along the way. His failure gave him the data he needed to pivot. But I have to say, that sounds like a one-in-a-million shot. This 'chase failure' mantra could be really dangerous advice for most people. You can't just keep banging your head against a wall, right?

Mark: You are absolutely right. And that's the nuance that makes this book so brilliant. It’s not just about blind persistence. Leak introduces a concept he calls "Never Give Up-ish." The "-ish" is the most important part. Michelle: "Never Give Up-ish." I like that. It’s got a built-in reality check. So how do you know when to be persistent and when to be... "ish"? Mark: He provides a framework for it, which he calls the Sweet Spot Matrix. Before you go all-in on a dream, you need to evaluate it against four criteria: Passion, Skillset, Opportunity, and Purpose. Michelle: Okay, that sounds a little like a business school buzzword. Break it down for me. What do those four things actually mean in practice? Mark: Passion is simple: it’s what you love, what you have natural energy for. Skillset is what you're actually good at, and he makes a key distinction: passion is self-verified, but a skillset needs to be verified by others. Opportunity is about what doors are actually open to you. And Purpose is the deepest level—it’s the "why" behind it all, the meaningful contribution you feel born to make. Michelle: That makes sense. You can be passionate about singing, but if you have a terrible voice, the skillset isn't there. Or you could be a skilled coder, but if there's no opportunity in your field, you're stuck. Mark: Precisely. And the most powerful story he uses to illustrate this isn't his own, but that of Condoleezza Rice. Michelle: The former Secretary of State? What does she have to do with this? Mark: Before she was a diplomat, Condoleezza Rice was a piano prodigy. She started playing at age three, practiced daily, and enrolled at the University of Denver at fifteen as a music major. Her dream was to be a world-class concert pianist. She had the passion and, by all accounts, a tremendous skillset. Michelle: So she had the first two boxes checked. What happened? Mark: She attended the prestigious Aspen Music Festival and found herself surrounded by other young prodigies. And she had a devastating realization. She watched twelve-year-olds play, by ear, pieces that had taken her a full year to master. She recognized they had an innate genius, an intangible gift that she, despite all her hard work, simply didn't possess. Michelle: Wow. That must have been crushing. To realize your best isn't good enough. Mark: It was. But instead of letting that failure define her, she used it as information. She went back to university that fall and walked into a class on international relations with a focus on the Soviet Union. And a new passion was ignited. She found her purpose. Michelle: Ah, so she realized the 'opportunity' to be a top-tier concert pianist wasn't truly there for her, even with her skill. That "failure" at the music festival was the data point she needed to make a better choice. Mark: You nailed it. Chasing failure isn't about martyrdom. It's about running an experiment. Condoleezza Rice's "failure" at the piano allowed her to pivot to a path where her passion, skillset, opportunity, and purpose all aligned perfectly. She gave up on one dream to find a much, much bigger one. She eventually became the first African American woman to be Secretary of State. And, in a beautiful full-circle moment, she even got to play piano for the Queen of England. Michelle: That is an incredible story. It completely changes the "never give up" narrative. Sometimes, giving up is the most strategic and courageous thing you can do. The wisdom is in knowing what to give up and when. Mark: That's the "ish." It's about being smart, not just stubborn. You chase the failure to see if the door will open. If it slams shut, you don't just keep knocking. You look around for a better door.

Michelle: So when you put these two ideas together, a really interesting picture emerges. It’s not just about being brave, and it’s not just about being smart. It’s about a cycle. Mark: It’s a two-part dance, exactly. First, you need the courage to chase failure, to step into the arena and risk public rejection like Ryan Leak did with his NBA tryout. You have to be willing to look foolish to find out where your limits are. Michelle: But then, you need the wisdom to interpret the results of that experiment. You need to analyze the failure and decide if it's a hurdle to overcome or a signpost pointing you in a new direction, like it was for Condoleezza Rice. Mark: And that's where the fear comes in. We're often too scared to even run the first experiment. The book is filled with stories of people—from Walt Disney to Steve Jobs to Oprah—who were fired or told they had no talent. Their initial failures were the catalysts for their greatest successes. They all had to "do it scared." Michelle: It seems like the real takeaway isn't just 'go fail.' It's 'go run an experiment.' The goal isn't the failure itself, but the clarity that comes from it. What's one small 'failure' you could chase this week, not to lose, but just to learn something? Mark: Exactly. It could be as simple as pitching an idea at work that you're 90% sure will get rejected, just to practice hearing 'no' and refining your pitch. Or signing up for a class in something you know you'll be terrible at, just to experience being a beginner again. Michelle: It really makes you wonder, doesn't it? What dream are you holding onto so tightly that it's stopping you from seeing a better one? What failure are you avoiding that might be the very thing that sets you free? Mark: A powerful question to end on. It’s about befriending failure, not defeating it. Michelle: This is Aibrary, signing off.