I didn’t set out to make a reading list. Honestly, most of the books I’ve found useful were ones I stumbled on. A friend mentioned it, or I saw it in a strange corner of a bookstore, or I picked it up, put it down, then picked it back up two years later when something in my life finally made me ready for it. What’s strange is, a lot of them weren’t directly related to work. Not in the obvious way. They weren’t books about “career growth” or “leadership hacks.” But they shifted something in me—how I make sense of chaos, how I ask questions, how I interpret what’s not being said in a room. So no, this isn’t a ranked list. I’m not trying to be helpful or definitive. I’m just trying to trace a line backward—through the ideas, arguments, phrases, and small turning points that stuck. Maybe some of them will stick with you, too. Maybe not. But either way, this is me writing it out. The Psychology of Money – Morgan Housel The Psychology of Money – Morgan Housel The Psychology of Money This one came into my life at a time when things were fine on the surface. I wasn’t panicking, but I was overthinking every financial decision. Not in a productive way—more like mentally spiraling around “what if I’m being reckless?” or “what if I’m being too cautious?” depending on the day. Housel’s writing felt like a quiet interruption. He doesn’t tell you what to do with your money. He shows you why two smart people can look at the same scenario and make opposite decisions—and still both be right, in context. What clicked for me was the idea that money is emotional history. It's shaped by what we saw growing up, what we fear, and what we believe about risk. After that, I stopped expecting my choices to make perfect sense to other people. And I stopped judging theirs. That alone gave me a lot more peace than I expected from a finance book. Orbiting the Giant Hairball – Gordon MacKenzie Orbiting the Giant Hairball – Gordon MacKenzie Orbiting the Giant Hairball There’s no other book like this one. It’s a weird little manifesto from a longtime creative at Hallmark—yes, greeting cards Hallmark. But it’s also one of the most honest things I’ve ever read about staying creative inside systems that slowly try to flatten everything into safe, predictable outputs. inside The first time I read it, I had no idea what I was supposed to take from it. It’s sketchy and nonlinear and slightly unhinged. But I remember one line: “To be fully human is to be creative.” That one stuck. Later, when I was in a role where everything felt like a compromise—more process, less spark—I came back to this book. It helped me realize that preserving creativity isn’t about being loud or rebellious. Sometimes, it’s about staying quietly weird inside a system that wants you to be efficient and beige. Antifragile – Nassim Nicholas Taleb Antifragile – Nassim Nicholas Taleb Antifragile I didn’t read this one in a single go. Actually, I hated it the first time I tried. Taleb’s writing style is—how do I say this—abrasive. It feels like he’s yelling at you while smirking. But the core idea wormed its way into my thinking and refused to leave. abrasive The idea is this: fragile things break under stress. Resilient things survive stress. But antifragile things—those get stronger because of stress. antifragile because of That completely rewired how I was looking at projects and systems. I had been aiming for resilience: can this withstand pressure? But Taleb pushed me to ask: can this actually benefit from unpredictability? What if the mess isn’t just survivable—it’s fuel? I still don’t agree with everything he says. But I think about that idea almost every time something breaks, and I’m tempted to just patch it back together and move on. The Score Takes Care of Itself – Bill Walsh The Score Takes Care of Itself – Bill Walsh The Score Takes Care of Itself This came at a time when I was feeling stuck—not dramatically, just… out of rhythm. I was managing a team, hitting goals, but something about the dynamic felt flat. People were going through the motions. Including me. Walsh, a legendary football coach, writes with the intensity of someone who believes every detail matters. And not in a performative, micro-managey way—more like, if your standard is excellence, then you don’t get to switch it off. You brush your teeth with it. You show up to meetings with it. You prepare small things with care because that’s who you are, not because someone’s watching. because that’s who you are That was both confronting and freeing. I wasn’t bringing that energy. And suddenly, it made sense why the culture felt loose. It wasn’t a vibe problem. It was a standard problem. Reading that book didn’t fix it—but it helped me name what needed to shift. standard The Art of Learning – Josh Waitzkin The Art of Learning – Josh Waitzkin The Art of Learning This one surprised me. I expected something practical or motivational. But what I got was strangely meditative. Waitzkin, who was the real-life chess prodigy from Searching for Bobby Fischer, talks less about chess or martial arts and more about the texture of mastery. Searching for Bobby Fischer It’s about how you get better—not in a linear, input-output way, but in waves. Plateaus. Regressions. Breakthroughs. And more importantly, how you observe yourself learning. yourself That lens stuck. I started to notice how I learned under pressure. How I reacted to being wrong. How I rushed through things when I felt insecure. It’s not a “10 rules for success” kind of book. It’s slower, gentler. And sometimes that’s exactly what you need. The Hard Thing About Hard Things – Ben Horowitz The Hard Thing About Hard Things – Ben Horowitz The Hard Thing About Hard Things This book has a misleading title. You think it’s going to be hard-nosed tactical wisdom. And sure, there’s some of that. But what it actually is—at least to me—is a long, conflicted letter about how lonely leadership can be when things go bad and there’s nobody left to blame. Horowitz talks about firing friends. Making impossible decisions. Having no good options, only less-worse ones. And not in a heroic tone—he’s often unsure, regretful, emotionally raw. I didn’t read this because I was leading a company. I read it because I was in a messy project with no clear path, and I needed to feel like the fog I was walking through wasn’t just me being bad at my job. That fog is real. It’s not a sign you’re failing. Sometimes, it’s just what it looks like to keep going. Bird by Bird – Anne Lamott Bird by Bird – Anne Lamott Bird by Bird This book is technically about writing. But I’ve applied it to almost everything. The title comes from a story she tells about her brother, overwhelmed by a school project on birds, and her father tells him: “Bird by bird, buddy. Just take it bird by bird.” That’s it. That’s the magic. It’s a book about imperfect starts, clumsy middles, and honest work. Lamott is funny, flawed, and entirely without ego. She writes like someone who’s tripped over her own mind enough times to know what real progress feels like—and what it doesn’t. Whenever I get frozen trying to make something good, this is the book I open. Not to get inspired. Just to remember: do the next small thing. The Fifth Discipline – Peter Senge The Fifth Discipline – Peter Senge The Fifth Discipline This book isn’t an easy read. It’s slow, thick, full of diagrams and systems language. But there’s a moment when it clicks—and once it does, you can’t unsee it. Senge’s core point is this: most organizational dysfunction is not about bad people. It’s about invisible systems. Feedback loops. Misaligned structures. Goals that contradict each other. And most of the time, we treat the symptoms instead of asking what the system is designed to produce. not That was a huge shift for me. It made me stop blaming individuals when things felt off. It gave me permission to look at the architecture. And slowly, that helped me influence change that actually stuck. Man’s Search for Meaning – Viktor Frankl Man’s Search for Meaning – Viktor Frankl Man’s Search for Meaning This is not a business book. It’s not even really a “self-help” book. It’s a record of survival. And a theory of purpose, built in one of the darkest human environments imaginable. I read it during a quiet period when I felt weirdly disconnected from everything I was working on. Like I was hitting all my goals, but none of it was moving me. Frankl doesn’t offer comfort. He doesn’t give you a process. He just says: if you can find meaning in your suffering, you can endure almost anything. moving It didn’t make me leap out of bed with inspiration. But it helped me get honest with myself. That’s more powerful, in the long run. The Mom Test – Rob Fitzpatrick The Mom Test – Rob Fitzpatrick The Mom Test This is the only book on this list that I would hand to someone with zero context and say: just read it, now. It’s short. It’s sharp. And it changed how I talk to people about ideas. The premise is simple: most people are too polite to give you honest feedback—especially when you ask bad questions. You think you’re validating your idea. You’re actually just collecting approval that doesn’t mean anything. This book helped me stop leading people into compliments. I started asking better questions. I started listening for what wasn’t being said. I’ve saved weeks of wasted effort just by remembering what I learned in 90 pages. That’s all of them! I don’t know if these books will land for you the way they did for me. Maybe you’ll love one. Maybe another won’t click at all. But if you’ve ever felt stuck, or foggy, or just unsure why something isn’t working the way it should—maybe one of these gives you a phrase, or a pause, or a shift. That’s how they worked for me. And that’s enough. That’s my reading list—for now, at least. If any of these books hit home, or if you’ve got one that changed how you think or work, hit reply and let me know. I love hearing what’s stuck with people—it almost always leads me to my next favorite read. And if you enjoyed this and want more slow, thoughtful content like it, feel free to share it or subscribe. I don’t write often, but when I do, it’s with intention. Until next time, keep learning, unlearning, and relearning folks.......

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Books That Found Me When I Wasn’t Looking

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