Michelle: What if the best career advice you ever got was wrong? That "follow your passion" is a trap, and getting fired might be the best thing that ever happens to you. Mark: Okay, you have my attention. Getting fired is good for me? I’m listening. My boss might be, too. Michelle: (Laughs) Well, today we’re looking at why the path to the top is never a straight line. We’re diving into the book Getting There: A Book of Mentors by Gillian Zoe Segal. Mark: A book of mentors. Sounds like it’s full of polished, perfect advice from people who never put a foot wrong. Michelle: That’s the brilliant part—it’s the exact opposite. What's fascinating is that the author, Gillian Zoe Segal, is a lawyer and photographer, not some business guru. She wrote this because she was tired of the myth of overnight success and wanted to show the messy, unfiltered reality of how people actually make it. Mark: The messy reality. I like that. So it’s not just a collection of "I woke up at 5 a.m. and conquered the world" stories? Michelle: Not at all. It all starts with dismantling this idea we have of the perfect career ladder.

Michelle: We’re all taught to build this perfect, linear résumé. Go to a good school, get the right internship, climb the corporate ladder. But Segal’s book argues that real success stories almost never look like that. In fact, her own journey is a prime example. Mark: How so? Michelle: She graduated from law school, passed the bar, and felt completely lost. She was anxious, uncertain, and knew she wasn't on the right path. Then, she read a commencement address by Cathy Guisewite, the cartoonist, who said, "When you remember what you love, you will remember who you are." For Segal, that was a photography class she’d taken. Mark: So she just dropped law and became a photographer? Michelle: Pretty much. She enrolled in a one-year program, came up with an idea for a photography book, and got rejected by agent after agent. But she persisted, pitched publishers directly, and eventually landed a deal. Her path was a total detour, driven by a moment of inspiration and a lot of grit. Mark: That’s a great story for the author, but what about the titans in the book? Surely someone like Warren Buffett had a master plan from day one. Michelle: That's the beauty of it! He did have a plan, and it failed spectacularly. He was famously rejected by Harvard Business School. He’d built his whole future around it and was devastated. Mark: Warren Buffett got rejected by Harvard? I had no idea. Michelle: He did. But that rejection forced him to look elsewhere. He discovered that his idol, the legendary investor Benjamin Graham, was teaching at Columbia. He applied, got in, and Graham became his mentor and changed his life. Buffett says getting rejected from Harvard was one of the best things that ever happened to him. The "failure" led him directly to the person who would shape his entire philosophy. Mark: Wow. So the detour was actually the direct path. Michelle: Exactly. And the book is filled with these stories. Leslie Moonves was a struggling actor before he became the CEO of CBS. Sara Blakely failed the LSAT twice before she ever thought of cutting the feet off her pantyhose and inventing Spanx. Mark: Okay, but what about someone like Jim Koch, the founder of the Boston Beer Company? The guy behind Sam Adams. He has multiple degrees from Harvard. That sounds pretty 'straight line' to me. Michelle: On the surface, yes. But he was miserable in his high-paying job at the Boston Consulting Group. He felt trapped. And this is where he introduces a brilliant idea he learned from his days as a mountaineering instructor: the difference between subjective and objective risk. Mark: Subjective versus objective risk? Break that down for me. Michelle: Subjective risk is what feels scary, like rappelling down a cliff. It looks terrifying, but the ropes can hold a car. It’s actually very safe. Objective risk is what seems safe but is secretly dangerous, like walking on a beautiful, sunny glacier in May. The melting snow can cause an avalanche at any moment. Mark: I see. So leaving his prestigious, high-paying job felt subjectively risky, but the objective risk was staying in a career that was slowly killing his spirit. Michelle: Precisely. The real danger wasn't starting a brewery; it was the risk of waking up at 65 having never done something he loved. He reframed the entire idea of what a "safe" path was.

Michelle: And that idea of risk leads directly to the second major theme in the book: failure isn't just an obstacle, it's raw material. Mark: Okay, I need a concrete example of that. How does getting fired from three jobs, like John Paul DeJoria, become 'raw material'? That just sounds like a terrible run of bad luck. Michelle: It sounds awful, right? But DeJoria, the co-founder of Paul Mitchell hair products and Patrón tequila, says those experiences were essential. Before he made it, he was so broke he was homeless and living in his car. One of his early jobs was selling encyclopedias door-to-door. Mark: That sounds like the worst job imaginable. Michelle: It was brutal. He said the average person lasted three days. He lasted three years. Why? Because every single day, he faced dozens of doors slammed in his face. He learned how to handle constant, relentless rejection and remain enthusiastic. That skill, that resilience, was the bedrock he built his entire empire on. Without that "failure" of a job, he would have never survived the early days of starting his own companies with just $700. Mark: So the failure was actually his training ground. Michelle: His ultimate training ground. But the most radical take on this comes from Spanx founder Sara Blakely. Her father didn't just tolerate failure; he actively encouraged it. Mark: What do you mean? Michelle: Every week at the dinner table, he would ask Sara and her brother, "So, what did you guys fail at this week?" If they didn't have an answer, he'd be genuinely disappointed. Mark: Wow. That is completely the opposite of how most of us are raised. He was disappointed if they didn't fail? Michelle: Yes! Because to him, failure wasn't about the outcome; it was proof that you were trying something new, that you were pushing your boundaries. It completely redefined failure for her. It became about not trying, rather than not succeeding. Mark: That completely reframes it. It's not about the result; it's about the attempt. It’s like a muscle you have to train. It makes me think of Michael Bloomberg getting fired from Salomon Brothers. He didn't see it as a failure, but as a severance package to start his own company. Michelle: Exactly! He was a partner, and they pushed him out. But he took his payout and immediately started building what would become Bloomberg L.P. He even said, "Living well is the best revenge." He turned that massive public rejection into the foundation of his fortune.

Michelle: This all builds to the final, and I think most profound, idea in the book, which is about who you're actually doing all this for. It's this concept of the 'Inner Scorecard' versus the 'Outer Scorecard.' Mark: Let me guess, the outer scorecard is what everyone else thinks—the job title, the money, the LinkedIn profile? Michelle: Precisely. It's all the external validation. And the inner scorecard is your own set of values, your own definition of success. Warren Buffett learned this from his father. He poses this incredible question: "Would you rather be the world's greatest lover, but have everyone think you're the worst? Or be the world's worst lover, but have everyone think you're the best?" Mark: That's a fantastic question. It cuts right to the core of it. Of course, it’s easy for a billionaire to talk about an inner scorecard. What about people who are just starting out, who are struggling to pay rent? Michelle: That’s a fair point, but the book shows it’s a mindset that has to start early. Take Matthew Weiner, the creator of Mad Men. He spent seven years writing the pilot script while working a full-time job in comedy. He had no outer validation. In fact, he had the opposite. The script was rejected by everyone, including HBO. Mark: Seven years on one script? That’s an incredible amount of faith in your own vision. Michelle: It’s the perfect example of the inner scorecard. He wasn't doing it for a paycheck or for praise. He was doing it because he believed in the story. He famously said, "A great idea is worthless; execution is everything." He was playing for an audience of one: himself. The same goes for Jeff Kinney, who wrote Diary of a Wimpy Kid. He worked on it in secret for eight years before he ever showed it to a publisher. Mark: And then there's Craig Newmark, the founder of Craigslist. He actively resisted monetizing the site in ways that would have made him vastly richer because it would have hurt the community. He was running the ultimate inner-scorecard business. Michelle: He absolutely was. His goal was never to maximize profit; it was to "give people a break" and create a useful community tool. He knew his own strengths and weaknesses, even hiring a CEO to run the company because he admitted he wasn't a good manager. He prioritized the health of the community over his own ego or wallet. That’s the inner scorecard in action.

Michelle: So when you pull it all together—the messy detours, the productive failures, the inner scorecard—the book's message becomes so clear. Success isn't a destination you arrive at after following a perfect map. It's the messy, unpredictable, and often beautiful byproduct of a life lived with resilience and authenticity. Mark: It’s about embracing the process, not just chasing the outcome. The book is called Getting There, but the real lesson seems to be that there's no 'there.' The journey is the point. The struggle, the rejections, the moments you feel lost—that’s not the stuff that happens before you succeed; that is the process of succeeding. Michelle: I love how Daniel Boulud, the famous chef, puts it. He says, "When you get kicked off your horse, the important thing is to get back on and ride with pride." All of these leaders, in their own way, learned to ride with pride, not in spite of their falls, but because of them. Mark: It really makes you wonder, what failure have I been avoiding that might actually be my next big opportunity? What detour am I afraid to take that might lead me exactly where I need to go? Michelle: That's the question to leave our listeners with. We'd love to hear your thoughts on this. Find us on our socials and share a time a 'failure' turned into an unexpected win for you. We all have those stories. Mark: This is Aibrary, signing off.