3 Books You Should Read Twice: Once in Your Youth, Again in Midlife
Introduction
If I could give my younger self a roadmap to navigate promotions, burnout, and feeling undervalued at work, I’d hand over three books. Each one gave me a different lens, but together, they cover the full picture. The three books are;
- Sun Tzu – The Art of War
- Marcus Aurelius – Meditations
- Dale Carnegie – How to Win Friends and Influence People
Life has a funny way of teaching lessons twice, once when we are too young to understand them, and again when we are old enough to wish we had learned them sooner.
In my case, these three books didn’t find their way into my life until mid-career. Reading them now, I can’t help but wonder how differently I might have handled certain challenges had I discovered them earlier.
Each of these books addresses a tension we all face:
- The desire to connect versus the struggle to communicate
- The urge to control circumstances versus the need to master ourselves
- The reality of competition versus the wisdom of strategy
These tensions are constants, but our approach to them evolves. That’s why I believe these three books deserve to be read at least twice: once in our late teens or early adulthood, and again as we approach or settle into midlife.
Sun Tzu – The Art of War - "Win first, then go to war."
On the surface, it’s a military strategy manual. But beneath that, it’s a guide for navigating the messy conflicts of life, personal, professional, even internal.
When I first picked up The Art of War, I expected battle metaphors. What I found was a toolkit for navigating difficult environments. In business especially, this book taught me that clarity, timing, and adaptability are more important than brute force. Know your enemy, yes, but also know yourself. And never go into battle without a plan. "In the midst of chaos, there is also opportunity."
Life Lessons learned with Life and Work:
Getting promoted: Focus on building rare skills, making yourself visible, and creating strong relationships. Promotions often happen before they’re announced.
Avoiding burnout: Don’t say yes to everything. Save your energy for the work that really matters.
Being undervalued: Don’t just do great work, make sure the right people notice it, even if that means being a little strategic about how you present it.
You have power over your mind, not outside events.
The most interesting fact about Meditations is that it's more of a journal than a book. Aurelius didn’t write for an audience, he wrote to himself. That’s what makes Meditations so powerful. These personal notes from a Roman emperor wrestle with fear, ego, time, and mortality in a way that still feels relevant centuries later.
This book reminded me that life throws you lemons, and is often beyond our control. The only thing we can truly govern is our response. Reading Meditations in midlife helped me detach from the noise, the rush, and the self-imposed pressure to do more and be more. It taught me that strength lies in restraint, and peace in acceptance.
"You have power over your mind, not outside events. Realize this, and you will find strength."
Life Lessons learned with Life and Work:
Focus: Stay calm and centered, no matter the chaos around you. Don’t take things personally, the obstacle is the way.
Promotion mindset: Do good work because it matters, not because you're waiting for someone to notice.
Burnout: Let go of what you can't control. Stress comes from trying to fix things that aren't yours to fix. Burnout is misalignment, act with purpose, not for praise
Undervaluation: Don’t carry resentment. Focus on your own growth and actions. Use criticism as fuel, not weight.
Dale Carnegie – How to Win Friends and Influence People
This classic isn’t about exploitation, it’s about understanding. Carnegie teaches that most people are far more interested in themselves than in you. Rather than resist that fact, he urges you to work with it, ask questions, show genuine interest, and offer appreciation without flattery.
When I read this book later in life, one truth hit hard: relationships are not just about communication, they’re about care. In my youth, I often focused on making my point. Carnegie helped me realize that real influence comes from listening, empathizing, and making others feel valued.
"You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you."
Life Lessons learned with Life and Work:
Focus: Influence without conflict. Think ahead and act with intention. Fight only when the ground is in your favor. Avoid office drama. Frame requests in ways that help others grow too.
Climbing the ladder: Be someone people enjoy working with. Praise others, listen more, and find ways to support the team’s goals. Position first, act later, promotions are won before the interview. Focus on building rare skills, making yourself visible, and creating strong relationships. Promotions often happen before they’re announced.
Getting noticed: If you want recognition, start by giving it. People often reflect what you give them. Even critics soften if you show understanding first.
Avoiding burnout: Don’t say yes to everything. Save your energy for the work that really matters. Don’t just do great work, make sure the right people notice it, even if that means being a little strategic about how you present it.
Conclusion
These books aren’t merely classics, they’re life manuals, like lighthouses in the fog, casting a steady light to guide me when the waves rise and the path ahead disappears.
Each one offers a mirror to who we are and a map to who we might become. Reading them young gives us guidance. Reading them again later gives us perspective.
Looking back, I wish I had read them sooner, but I’m grateful I read them at all. If you’re just starting out, read them now. If you’re already well into life's journey, read them. You might be surprised by how differently the world looks when seen in a new light.
Reading them when we are young, and again when older, our view to them evolves. That’s why I believe these three books deserve to be read at least twice: once in our early adulthood, and again as we approach or settle into midlife.
Stay nerdy. Stay bold. Stay kind.
— MindTheNerd.com