If you’re anything like me, you’ve probably noticed that retirement doesn’t feel like the rocking-chair-and-bingo-card version we were promised in the brochures. Instead, it feels more like, “Okay, now what?” Enter the new wave of retirees: those of us who want more than daytime TV reruns and waiting for the mailman. We want freedom, creativity, and—let’s be honest—a bit of extra cash that doesn’t come from the government’s stingy monthly check.
One of the best ways to start? Books. And no, I don’t mean 50 Shades of Sudoku (though I’d read that). I mean books that fuel both your online business savvy and your mindset for this new chapter of life. Below, I’ve rounded up some gems that can help you rewire your brain, build confidence with technology, and set up shop in the digital world. Think of these as the instruction manuals we never got for “retirement 2.0.”
1. The $100 Startup by Chris Guillebeau
This is a must-read if you want to launch an online business without draining your life savings—or pawning off your golf clubs. Guillebeau breaks down how people all over the world started businesses on a shoestring budget and turned them into full-time ventures. The best part? Many of these ideas don’t require advanced tech skills. Perfect if you’re still asking your grandkids how to use the TV remote.
Takeaway: You don’t need millions to start—sometimes $100 and a strong cup of coffee is enough.
2. Building a StoryBrand by Donald Miller
Starting an online business is one thing. Getting people to actually pay attention to it? That’s another story—literally. Miller shows you how to clarify your message and make your audience feel like the hero of the story (instead of glazing over at your “About Me” page). This book is like learning to speak “customer-ese” without needing a dictionary.
Takeaway: Stop telling people what you do. Start showing them how you make their lives better.
3. You Are a Badass at Making Money by Jen Sincero
The title alone makes me want to sit up straighter. Retirement sometimes comes with a scarcity mindset—we think our best earning years are behind us. Nonsense. Sincero delivers a hilarious yet practical guide to rewriting those money scripts in your head. Consider this your pep talk for embracing abundance while sipping a mocktail on your porch.
Takeaway: You’re not “too old” to build wealth. You’re just seasoned enough to do it smarter.
4. Ikigai: The Japanese Secret to a Long and Happy Life by HĂ©ctor GarcĂa and Francesc Miralles
Online business aside, retirement is also about finding joy and purpose in your day-to-day life. This book explores the concept of ikigai—your reason for getting up in the morning. Spoiler: it’s not just about profit margins or affiliate links. Pairing this with your entrepreneurial projects can help you design a lifestyle that’s both meaningful and sustainable.
Takeaway: A fulfilling retirement is about purpose, not just profit.
5. The E-Myth Revisited by Michael E. Gerber
This one is for those of us who are ready to roll up our sleeves and treat our online business like a “real” business. Gerber explains why so many small businesses fail (hint: it’s usually the owner trying to do everything). Then, he shows you how to set up systems that make your business run without you working 24/7. Because let’s face it, we’d like to enjoy some sunsets too.
Takeaway: Don’t just work in your business—learn to work on it.
6. Crushing It! by Gary Vaynerchuk
If you’ve ever thought social media is only for kids doing dance challenges, Vaynerchuk will change your mind. Crushing It! is all about using social platforms to build your brand, connect with your audience, and turn followers into customers. His case studies of real people (many who started with no experience) prove it’s never too late to jump into the digital game.
Takeaway: Social media isn’t a young person’s playground—it’s a business tool, and you can use it to grow your retirement venture.
7. The Lean Startup by Eric Ries
Let’s face it: nobody wants to waste years building an online business idea only to find out nobody wants it. Ries teaches you how to test your ideas quickly, adjust on the fly, and keep the momentum going without draining your savings or your patience. It’s like having a business coach whispering, “Stop overthinking, just test it already.”
Takeaway: The faster you test and learn, the faster you’ll find what actually works.
Why These Books Matter for Retirees
Choosing the right books after 60 isn’t just about staying busy. It’s about staying relevant. Business trends shift, technology evolves, and keeping up gives us an edge—not to mention a brain workout better than any crossword puzzle.
Books like these help bridge the gap between our decades of wisdom and the fast-paced digital world. They offer both practical know-how and mindset shifts that remind us retirement is not an end—it’s an opportunity to reinvent.
Bringing It All Together
Whether you’re launching a blog, dabbling in affiliate marketing, or just want to finally understand what your grandkids mean when they say “algorithms,” these reads will help. They’ll give you tools, confidence, and maybe even the kick in the pants you didn’t know you needed.
So brew a strong cup of coffee or your favorite tea, grab one of these books, and start plotting your next adventure. Because retirement? It’s not the end of the story—it’s the sequel.
👉 Your turn: What books have inspired you in this chapter of life? Drop them in the comments—I’m always looking for my next read.
Happy Reading,
Lisa Renee
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