Looking back on my 20s, I had my share of wild nights, risky moves, and lessons learned the hard way. But there’s one thing I would have done differently: I would have spent a lot more time with my nose in the right books. These aren’t your average reads; they’re game-changers. Here’s the list of books I wish I’d had back then and why each one could’ve set me up for success, growth, and a sharper sense of purpose earlier in life.
1. The 5 AM Club by Robin Sharma
This book is like a wake-up call, literally. Sharma breaks down how waking up at 5 AM can transform your productivity, mindset, and health. If I’d learned about the power of those early morning hours in my 20s, I probably would’ve gotten a head start on everything. The 5 AM habit isn’t just about waking up early; it’s about making space for yourself, for reflection, and for goals. I didn’t realize back then how a simple shift in my schedule could open up so many opportunities.
2. The Automatic Millionaire by David Bach
In your 20s, money management isn’t usually top of mind, but it should be. The Automatic Millionaire breaks down how you don’t need to be rich to become wealthy — you just need to start with the right habits and make saving automatic. Bach’s strategies for building wealth without getting bogged down in complicated finance jargon could’ve made a huge difference for me. If I’d read this book early on, I might’ve skipped a lot of those late nights with maxed-out credit cards and the stress that followed.
3. Relentless by Tim S. Grover
If you’ve ever felt like you were coasting instead of pushing yourself, Relentless will hit you hard. Grover, who trained some of the greatest athletes, including Michael Jordan, Kobe Bryant, and Dwyane Wade, lays out what it takes to reach that next level of greatness. He doesn’t sugarcoat it: excellence requires an obsessive, relentless drive. Had I read this book in my 20s, I might’ve approached my goals with more intensity and focus, refusing to settle for “good enough.”
4. Deep Work by Cal Newport
We live in a world of constant distractions, and Newport’s Deep Work is all about cutting through the noise to do meaningful, high-level work. In my 20s, I spent too much time multitasking, thinking I was being productive. Newport’s book would’ve taught me that deep focus isn’t just a productivity hack — it’s essential for standing out and achieving mastery. This book would have saved me from a lot of wasted time on trivial tasks and kept me focused on my goals.
5. The Way of the Superior Man by David Deida
This one’s more than a self-help book; it’s a guide for men on understanding masculinity, relationships, and purpose. Deida explores the balance between ambition and connection, urging men to find a purpose beyond themselves. In my 20s, I was all about the hustle, but this book would’ve shown me how to balance ambition with integrity and respect for others. It’s about being grounded, confident, and committed to a higher purpose, something I only learned to appreciate later.
6. The Obstacle is the Way by Ryan Holiday
Life throws challenges at us constantly, and Holiday’s The Obstacle is the Way teaches how to see setbacks as opportunities. If I’d read this in my 20s, I’d have approached challenges differently, understanding that every roadblock is a chance to grow and adapt. Instead of seeing obstacles as setbacks, Holiday frames them as paths to success — a mindset that would have saved me a lot of frustration and taught me resilience early on.
7. Atomic Habits by James Clear
Atomic Habits is all about making small, consistent changes that compound over time. Clear’s practical advice on building good habits and breaking bad ones would have been a godsend back in the day. I would’ve learned that success isn’t about grand gestures; it’s about small, daily actions. By focusing on 1% improvements, Clear’s philosophy would’ve helped me establish routines that actually stick and ultimately drive big changes.
8. Why Should White Guys Have All the Fun? by Reginald F. Lewis
This is the story of Reginald Lewis, one of the first Black billionaires in America, and his journey through law, business, and breaking barriers. This book is both an inspiring biography and a powerful testament to the power of self-belief and resilience. If I’d read this in my 20s, it would’ve been a powerful reminder that there are no limits when it comes to ambition. Lewis’s life teaches that the only barriers are the ones you accept.
9. Influence: The Psychology of Persuasion by Robert B. Cialdini
Everyone should understand the basics of influence and persuasion. Whether it’s in relationships, work, or life in general, knowing how to connect with people and understand their motivations is huge. Cialdini’s principles on reciprocity, commitment, social proof, and more would’ve given me an edge in navigating both personal and professional interactions. This book is like a playbook for understanding how people tick — and that’s knowledge you can take anywhere.
10. Can’t Hurt Me by David Goggins
If you need a lesson in mental toughness, David Goggins is your guy. In Can’t Hurt Me, Goggins shares his story of overcoming poverty, abuse, and a life of struggle to become a Navy SEAL, ultra-marathoner, and one of the world’s toughest men. Goggins’ story would’ve slapped some sense into 20-something me, showing me that our limitations are self-imposed and that we’re capable of so much more than we think. It’s a no-excuses approach to life that teaches you to push beyond what you believe is possible.
Final Thoughts: Books as Life Lessons
If I’d had these books in my 20s, I’d have entered my 30s with more discipline, focus, and a clearer sense of purpose. Each one of these books offers a lesson that goes beyond the page, impacting how you live, work, and relate to others. They’re not just reads; they’re roadmaps to living a life with intention, strength, and wisdom. So if you’re in your 20s — or honestly, at any age — grab these books, dive in, and start leveling up.