Shakespeare: As a product manager, you live and die by expectations. The roadmap, the stakeholders, the launch date. But what if the most dangerous expectations aren't in your project plan, but in your own head? What if your mind is running on buggy, outdated software, programmed by others, and it's about to crash your entire system?

tahmin: That's a terrifying thought, but also an incredibly familiar one for anyone in a high-pressure environment. It feels like you're constantly trying to meet a set of requirements you didn't even write.

Shakespeare: Precisely. And in his book "Living Free," DeVon Franklin calls this the 'secret software' running your life. It’s a powerful metaphor we’re going to unpack today with our guest, tahmin, a product manager in the tech industry who is an expert in managing complex systems and, well, expectations. Welcome, tahmin.

tahmin: Thanks for having me. I'm fascinated by this idea of applying engineering principles to our own psychology.

Shakespeare: Then you are in the right place. Today, we're going to explore this from two angles, specifically for a strategic thinker like you. First, we'll explore the idea of your mind as an operating system and how to debug the unrealistic expectations that cause it to crash. Then, we'll discuss how to build an 'agile career' by prioritizing process over promotion, ensuring long-term success and fulfillment.

Shakespeare: So, tahmin, as someone who builds and manages products, how does this idea of our minds running on 'secret software' land with you?

tahmin: It lands perfectly. It's like we're all running on legacy code we didn't write ourselves. In product development, we call that 'tech debt'—it's the implied cost of rework you incur by choosing an easy, but limited, solution now instead of using a better approach that would take longer. It sounds like what the book is describing is a kind of 'emotional debt.' We adopt these easy, pre-packaged expectations from our family or society, and they work for a while, but eventually, the system becomes unstable and the debt comes due.

Shakespeare: What a brilliant frame. Emotional debt. And this 'software,' this code, is often installed in the vulnerable days of our youth. DeVon Franklin tells his own story of becoming 'Mr. Perfect.' He grew up in a chaotic home; his father was an alcoholic and often absent. So, to create a sense of order and to win the attention he craved, young DeVon learned he had to be flawless. He got straight A's, he became a leader in every club. This became his operating system, the core code: 'Perfection equals Safety and Love.'

tahmin: It's a survival mechanism that gets hard-coded into the system.

Shakespeare: Exactly. But this code had a bug. A critical one. It made him utterly intolerant of mistakes, his own or others'. It filled him with anxiety. His whole system was brittle, ready to shatter at the first sign of imperfection. The book argues that much of our stress—like the Gallup data showing 55% of Americans feel stressed out—comes from this kind of buggy software, this gap between our coded expectations and reality.

tahmin: That's a powerful origin story for a bug. In the tech world, we see this in company culture all the time. A founder's early anxieties, maybe a fear of being too slow, can become institutionalized as a 'move fast and break things' mantra. That works when you're a five-person startup. But when your product is used by millions, 'breaking things' means losing trust, losing data, losing money. At some point, you have to make a conscious decision to deprecate that old code. So, how does the book suggest we even find these bugs in ourselves?

Shakespeare: By recognizing their manifestations, the error messages they produce. The book identifies four key forms they take: assumptions, standards, judgments, and projections. An assumption, for instance, is defined as 'treating a possibility as a certainty.' You assume that because you worked hard on a project, you get the promotion. That's a huge one in professional life.

tahmin: Oh, absolutely.

Shakespeare: A standard is when you impose your personal level of quality on a teammate. You might work until 10 PM every night, and you start to resent a colleague who logs off at 5 PM, even if their work is excellent. You've turned your personal standard into a judgment against them.

tahmin: That's the daily life of a Product Manager in a nutshell. Managing stakeholder assumptions, aligning different team standards, preventing my own biases from becoming unfair judgments. It's fascinating. The book is essentially providing a framework for emotional QA—Quality Assurance. You have to constantly test your own thinking to make sure it's sound.

Shakespeare: And if you don't, that emotional debt you mentioned just keeps compounding.

Shakespeare: Exactly, emotional QA. And a failure in that QA can lead to a system-wide crash. This brings us to our second point, which is a perfect, if painful, example of this. It's about what happens when you pour everything into a single outcome, a single 'product launch' for your life, and it fails. It's the story of the "Karate Kid" remake.

tahmin: I'm ready for this. It sounds intense.

Shakespeare: It is. Picture this: DeVon Franklin is a rising executive at Sony Pictures. He's given a monumental task: oversee the remake of 'The Karate Kid.' This isn't just any film; it's a huge gamble, filming in Beijing, China, which was a logistical nightmare. He travels to China nine times in nine months. He's working around the clock, taking calls from the production team in Beijing in the middle of the night from his L. A. office. He pours his life into it.

tahmin: All in on one project. High risk.

Shakespeare: The highest. And the film is a colossal, out-of-the-park home run. It grosses $359 million worldwide on a tiny $40 million budget. He has done the impossible. He walks into his boss's office, confident, ready for the reward he has earned, the promotion he expects. And the answer is no.

tahmin: Oh, that's brutal.

Shakespeare: Crushing. The reason given was that there were already too many senior executives; the company structure just couldn't support it. He was told to go back to supporting other executives on their movies. He describes being completely devastated, unmotivated for months. His entire sense of self-worth had been tied to that one result.

tahmin: Wow. That is a brutal story. And it's the ultimate 'waterfall' approach to a career. In old-school software development, you'd spend two years building something, with one single point of validation at the very end—the launch. If it failed, the entire project was seen as a failure. He invested years of effort for one binary outcome.

Shakespeare: And the 'no' broke him.

tahmin: In the agile world, we try to avoid this at all costs. We deliver value in small, iterative cycles called sprints. You get feedback every two weeks. You celebrate small wins. You learn and adapt constantly. The health of the team and the process is just as important as the final product. You're not waiting two years for a single 'yes' or 'no' from the market.

Shakespeare: And that is precisely the epiphany he had! He realized, in his words, that he had to 'break his addiction to results.' He was addicted to the outcome, not the process. He found a quote from Warren Buffett that became his new mantra: 'We enjoy the process far more than the proceeds.' Franklin realized his true joy wasn't in the title or the promotion; it was in the. That's when he decided to start his own production company, where he could control the process itself.

tahmin: That's the critical shift from being a feature-focused PM to a vision-focused leader. You stop just shipping things and start building a sustainable, creative engine. It’s about falling in love with the problem-solving, the collaboration, the craft itself. The promotions, the success—those become byproducts of a great process, not the sole goal. When your process is strong, the results tend to follow, but your happiness isn't entirely dependent on them.

Shakespeare: You've captured the soul of it. He learned to love the climb more than the summit.

Shakespeare: So, we have these two powerful, intertwined ideas from "Living Free." First, that we must become conscious developers of our own mental 'software,' debugging the expectations that hold us back and lead to that 'emotional debt.'

tahmin: And second, that we must adopt an 'agile' mindset for our lives and careers, finding joy and success in the daily process, not just in the final, often uncontrollable, result.

Shakespeare: It's a move from being a passive character in your own story to the active author.

tahmin: Or, to stick with the metaphor, it's about moving from being a passive user of your own life to becoming the lead product manager of your own experience. You own the roadmap. You define the success metrics.

Shakespeare: Beautifully put. So, for everyone listening, here's a thought experiment from the book, a piece of actionable advice. The author talks about performing a 'cost-benefit analysis' on your life. This week, find one thing you do—professionally or personally—simply because you feel you 'should.'

tahmin: That one meeting you attend that has no clear agenda, or that family obligation you dread every month.

Shakespeare: Yes. And ask yourself: What is the true cost of this expectation? In your time, in your energy, in your joy? And what is the real, tangible benefit? The answer might just be the first line of code you decide to rewrite in your own operating system.

tahmin: I love that. It's a small, analytical step toward reclaiming your own life. It's the first step in a new sprint.

Shakespeare: The first step to living free. Tahmin, thank you for bringing such a sharp and insightful perspective to this.

tahmin: It was my pleasure. This was a fantastic conversation.