Michelle: Alright Mark, I'm going to give you the title of a book, and you have to guess the author's most stressful day at work. The book is Bet on Yourself. Mark: Bet on Yourself... okay. Most stressful day? Probably the day they accidentally replied-all to a company-wide email with a bad meme. Michelle: Close. Try: the day she almost killed Jeff Bezos. Mark: Hold on, what? That’s a heck of an opener. You can’t just drop that and walk away. Michelle: I promise we will get to that story, because it’s absolutely central to the book we’re discussing today: Bet on Yourself: Recognize, Own, and Implement So You Can Win in Business and Life by Ann Hiatt. Mark: Ann Hiatt. I’m guessing she didn’t start her career in workplace safety. Michelle: You could say that. What's so fascinating about her is that she was a total outsider. She was at UC Berkeley, deep into a PhD program in Scandinavian Studies, of all things, before she pivoted and landed a job as Jeff Bezos's executive assistant in the early 2000s. She went from Viking sagas to the inner sanctum of Amazon. Mark: That’s a wild career change. And the book has had a really interesting reception, right? It’s not your typical business guide. Some readers see it as this incredible, inspiring insider story, but others have pointed out that her path—getting direct access to these tech titans—isn't exactly replicable for everyone. It feels more like a memoir than a manual. Michelle: That’s the perfect tension to explore. Because Hiatt argues the principles are universal, even if the circumstances are unique. And her first big idea is about actively seeking out those very 'irreplicable' opportunities.

Mark: Okay, I’m curious. What exactly does she mean by an 'irreplicable opportunity'? Is that just a fancy term for a lucky break? Because getting hired by Jeff Bezos sounds like winning the career lottery. Michelle: It does, but her story of how she got hired is the key. This was 2002, the dot-com bust was in full swing, and jobs were scarce. She applies for this junior assistant role at Amazon. She goes through months of grueling interviews with senior VPs who are trying to find her breaking point. Mark: Sounds fun. The classic corporate stress test. Michelle: Exactly. But the final interview is with Bezos himself. He sits down, looks at her, and asks two questions. The first: "What are your career goals?" She gives a standard ambitious answer. Then he leans in and says, "I have a fun one for you. I want you to estimate the number of panes of glass in the city of Seattle." Mark: Come on. That’s one of those brain-teaser questions that I thought only existed in urban legends about tech interviews. What does that have to do with being an assistant? Michelle: Nothing and everything. He wasn't looking for the right answer. He was looking for the right process. He wanted to see how she would break down an impossible problem into logical, manageable parts. So she starts thinking out loud: "Okay, let's start with the population of Seattle, assume each person has a house, a car, an office... each of those has a certain number of windows..." She builds a model from the ground up. Mark: And he’s just watching her do this? Michelle: He’s watching her think. After a few minutes, he smiles and says, "You're hired. You start Monday." He didn't ask about her typing speed or her scheduling software skills. He hired her for her grit and her problem-solving intelligence. That’s what Hiatt means by an irreplicable opportunity. It’s a role where you are valued for your potential to learn, not just your existing skills. Mark: I can see that, but it still feels very specific to that Silicon Valley, 'move fast and break things' culture. What's the takeaway for someone working at, say, a mid-sized insurance company in Ohio? They’re probably not asking you to count windows. Michelle: The principle isn't about the quirky question; it's about prioritizing learning over the ladder. Hiatt’s point is to look for the person, not the position. Work for someone who will challenge you, who is brilliant, who will push you into situations where you have to learn at an accelerated rate. It’s a mindset shift. Instead of asking, "What will my title be?" ask, "Who will I be learning from?" Mark: That makes more sense. It's less about finding a billionaire and more about finding a mentor who will throw you in the deep end. Michelle: Precisely. And it doesn't have to be a glamorous job. Hiatt brings up the story of Sara Blakely, the founder of Spanx. Before she became a billionaire, she sold fax machines door-to-door for seven years. A soul-crushing job by any measure. Mark: Oh, I can only imagine the rejection. Michelle: But Blakely credits that job with her success. She says it was her real-world MBA in sales and, more importantly, in resilience. She learned how to handle rejection, how to be persuasive, and how to keep going. That wasn't a glamorous opportunity, but the learning was irreplicable. She was betting on the skills she was building, not the job she had. Mark: So you’re saying the 'irreplicable opportunity' is one that gives you scars you can learn from. It’s about finding a role that forces you to grow, even if it’s uncomfortable. Michelle: Exactly. It’s about choosing the high-growth, high-pressure environment. Which, of course, sounds like a recipe for spectacular failure. And in Ann Hiatt's case, it almost was.

Mark: Right, you can’t leave me hanging. The Jeff Bezos story. How do you almost kill one of the most powerful CEOs on the planet and still have a job, let alone write a book about it? Michelle: This story is the absolute core of the book's message about resilience. It’s early 2003. Amazon isn't the behemoth it is today; it’s still fighting for profitability. Jeff Bezos's leadership is everything. He comes to Ann and says he needs to visit several properties in rural West Texas in a very short amount of time. Mark: A classic impossible boss request. Michelle: She looks at the map, the travel times, and realizes the only way to do it is by helicopter. Her manager tells her, "No is not an answer," so she finds a charter company and books it. A few weeks later, she’s at her desk in Seattle, and she gets a call from the pilots of Amazon's private jet. They say they just heard an emergency beacon go off from a helicopter in West Texas. The one she chartered. Mark: Oh my god. My stomach just dropped. Michelle: Hers too. She describes this cold dread, this absolute certainty that she has just killed Jeff Bezos and, by extension, maybe even Amazon itself. She has no protocol for this. No one does. So she just starts acting. She pulls up a map, starts calling every single hospital in that remote part of Texas, asking if they have a patient named Jeff Bezos. Mark: That’s incredible presence of mind. I think I’d just be hiding under my desk. Michelle: She keeps hitting dead ends. Finally, she gets a hospital administrator who says, "I can't tell you anything, but a reporter from the local paper just called asking about a helicopter crash near Cathedral Mountain." So Ann hangs up, calls the newspaper, and gets the reporter's cell number. She calls him, and he tells her, "Oh yeah, the helicopter went down. But I heard the guy who was on it was a real hero, helped pull the pilot out of the wreckage." Mark: No way. That was Bezos? Michelle: That was Bezos. He survived the crash, basically unharmed, and immediately went into problem-solving mode. He called the Amazon board and told them to bury the story. A few hours later, he calls Ann. She’s expecting to be fired, obviously. But the first thing he says to her is, "Ann, I hear you’re really good under pressure." Mark: Wow. Just... wow. That’s not the reaction I would expect. He saw her competence in the chaos, not the mistake that led to it. Michelle: That's the entire point. In these high-stakes environments, your response to failure is infinitely more valuable than a perfect track record. She didn't panic. She gathered information, she communicated clearly, she solved the problem. She earned his trust in that moment of crisis in a way that a year of perfectly scheduled meetings never could have. Mark: It’s like that photography class experiment she mentions, right? The one where the professor divided students into two groups. Michelle: Exactly. One group was graded on the quantity of photos they produced—a hundred photos got you an A. The other group was graded on the quality of a single, perfect photo. At the end of the semester, all the best photos came from the quantity group. Mark: Because they were just shooting, experimenting, making mistakes, and learning with every click. The 'perfection' group was so paralyzed by the fear of producing a single flawed image that they never really learned anything. Michelle: They were paralyzed. Hiatt's argument is that your career should be like the quantity group. You need to take lots of shots, make mistakes, and pivot quickly. The helicopter crash was a massive, terrifying mistake, but her quick pivot built resilience and trust. That trust is what gets you in the room for the big decisions. But as she learns later, just being in the room isn't enough.

Michelle: And that trust is what gets you in the room. But Hiatt argues that just being in the room isn't enough. You have to eventually earn your own seat at the table. Mark: Which is where the imposter syndrome really kicks in, I imagine. You’ve survived the helicopter crash, you’re in the inner circle, and now you’re surrounded by geniuses, probably feeling like you don't belong. Michelle: One hundred percent. She tells this amazing story from years later when she was at Google, working as Chief of Staff for Eric Schmidt. They're in Madrid for a meeting with the newly crowned King of Spain. It’s just Eric, the King, and a policy lead. But Eric insists that Ann come into the room. Mark: That’s a high-pressure situation. What do you even say in a room with a CEO and a King? Michelle: That's what she was thinking! She felt like a total fraud. She said the King wasn't even staffed; it was just him. So she felt this immense pressure to justify her presence. She sat there silently, listening, until Eric turned to her and asked for her observations. And in that moment, she realized something profound. Mark: What was that? Michelle: She didn't just want to be in the room where it happens; she wanted to earn her seat. She realized you can't wait to be invited or given a role. Sometimes, you have to bring your own folding chair. Mark: That’s a powerful metaphor. But what does 'bringing a folding chair' actually mean day-to-day? Is it just about speaking up more in meetings? Michelle: It's more strategic than that. It’s about fundamentally reframing your job. She says most people see their job as a list of tasks to be completed. But to become indispensable, you have to see your job as a mission: "My purpose is to make my leader, my team, and my company successful." Mark: So it’s a shift from reactive to proactive. You’re not just doing what you’re told; you’re anticipating needs. Michelle: Exactly. She calls it "managing up." She did this for Marissa Mayer by streamlining her overwhelming speaking requests. She did it for Larry Page by creating the "Eng Chats" program so he could reconnect with his top engineers. She took problems off their plates before they even had to ask. She wasn't just doing her job; she was creating value that made her team, her 'squad' as she calls it, "embarrassingly good." Mark: 'Embarrassingly good.' I love that. It’s about making yourself so useful that your absence would create a noticeable hole. You’re not just a cog in the machine; you’re part of the engine. Michelle: That’s the perfect way to put it. You stop waiting for permission and start taking ownership. You bring the chair, you set it down, and you start contributing. That’s the final bet you make on yourself. It’s not just about getting the job or surviving the chaos; it’s about actively shaping your role and your impact.

Mark: So it seems the thread connecting all this is that you don't build an extraordinary career by playing it safe and climbing a predictable ladder. You find a rocket ship, you hold on tight through the turbulence, and then you figure out how to help fly the thing. Michelle: Exactly. And Hiatt's journey forces us to ask a really uncomfortable question: Are we building a career that's safe, or one that's valuable? Are we spending our energy avoiding failure, or are we using it to learn from our mistakes? Mark: It’s a challenge to the whole idea of a 'comfort zone.' She argues that the most successful people are the ones who are constantly pushing their boundaries, who are comfortable with being uncomfortable. Michelle: She has this great line that really stuck with me. She says, "Actual joy lives in the attempt and not just the summit of our personal mountains." It’s about finding fulfillment in the process of doing hard things. Mark: That’s a much more sustainable way to think about a career. It’s not about reaching some final destination, but about the growth you experience along the way. It’s a powerful idea. Michelle: It really is. And it makes you think about the bets you’re placing in your own life. It’s a powerful question. We'd love to hear what you think. What's the biggest bet you've ever made on yourself? Find us on our socials and let us know. Mark: This is Aibrary, signing off.