After sharing my first list of ten books that shaped my business mindset and skills, I realized there were still plenty more sitting on my shelves that have been just as influential. Online entrepreneurship isn’t a straight path — it’s a constant mix of creativity, strategy, resilience, and reinvention. And the books that help us along the way tend to cover all of those angles.
This second list includes titles that pushed me past procrastination, helped me rethink branding, and reminded me how powerful stories are in both life and business. If Part 1 was about foundations, this list is about sharpening your edge and expanding your perspective.
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1. Guerrilla Marketing for Coaches: Six Steps to Building Your Million-Dollar Coaching Practice by Jay Conrad Levinson & Andrew Neitlich
Even if you’re not a coach, this book is pure gold for service-based entrepreneurs. It lays out practical marketing moves you can implement without massive budgets or big teams. What stuck with me most was how creative marketing doesn’t require reinventing the wheel — it requires being consistent and smart about visibility.
I applied several of their tactics to my consulting offers years ago and saw immediate results. If you do coaching or freelancing, this one’s a blueprint.
2. Time Warrior: How to Defeat Procrastination, People-Pleasing, Self-Doubt, Over-Commitment, Broken Promises and Chaos by Steve Chandler
The title alone made me laugh the first time I saw it — because it listed every single trap I fall into. Procrastination? Check. Over-committing? Definitely. Self-doubt? Absolutely.
Chandler’s approach is unconventional. He doesn’t hand you a calendar system or color-coded productivity hack. Instead, he reframes how you think about time and action. His writing is blunt, funny, and sometimes uncomfortable, but it gets you moving. For me, it was the kick I needed to stop wasting so many hours second-guessing myself.
3. The Power of Story: Change Your Story, Change Your Destiny in Business and in Life by Jim Loehr
This book made me look at the story I was telling myself about who I was and what I could achieve. Loehr argues that the narratives we live by shape everything — from our health to our business outcomes. My mentor and friend Craig Desorcy recommended this one to me.
I started noticing the little stories I’d repeat, like “I’m bad with technology” or “I’ll never be as polished as whatever guru you envy.” Once I realized I could rewrite those stories, I felt lighter. This book is especially powerful for entrepreneurs who feel stuck in a loop of self-doubt.
4. The War of Art: Break Through the Blocks and Win Your Inner Creative Battles by Steven Pressfield
This is the book I go back to whenever resistance hits. Pressfield personifies resistance as an enemy you must fight daily if you want to create. He doesn’t sugarcoat it.
When I first read it, I was struggling with writing consistently. After finishing it, I started treating my writing time like a non-negotiable battle. I showed up whether I felt inspired or not. That shift alone made me infinitely more productive.
5. The Art of Learning: An Inner Journey to Optimal Performance by Josh Waitzkin
Josh Waitzkin was a chess prodigy who later became a world champion in Tai Chi Push Hands. His book explores how the principles of learning apply across disciplines.
What I loved was how he described getting into “the zone” and how to train yourself to access it faster. For me, this translated into writing flow. By treating my writing sessions more like training sessions, I got better at slipping into deep focus instead of wasting the first hour “warming up.”
6. Profiles of Power & Success: Fourteen Geniuses Who Broke the Rules by Gene N. Landrum
This book is a fascinating collection of case studies. Fourteen different innovators, from various industries, who didn’t follow the playbook — and that’s exactly why they succeeded.
As an entrepreneur, it reminded me that being unconventional isn’t a weakness. It’s often the very thing that makes you stand out. When I read about how these people refused to accept the “normal” way of doing things, it gave me permission to lean harder into my own quirks and unorthodox methods.
7. Sparks of Genius: The Thirteen Thinking Tools of the World’s Most Creative People by Robert Root-Bernstein & Michèle Root-Bernstein
This is part creativity manual, part science book. It dives into how innovators think — and then shows you how to apply those same methods.
I started using some of their techniques, like “analogizing” and “pattern recognition,” in brainstorming sessions. It gave me fresh ways to solve business problems instead of always leaning on the same linear approach. If you ever feel stuck, this book sparks new ideas.
8. Accidental Branding: How Ordinary People Build Extraordinary Brands by David Vinjamuri
This one hit home for me because it’s about entrepreneurs who didn’t go in with slick branding plans or million-dollar ad budgets. They were ordinary people who stumbled into building brands that resonated deeply with their audiences. Vinjamuri highlights stories of companies like Burt’s Bees and Clif Bar, brands that grew not because they had the best logos or the flashiest campaigns, but because they had a story people cared about.
As an online entrepreneur, this was a wake-up call. It reminded me that branding isn’t just fonts, colors, or taglines. It’s the sum of how people feel about your business and why they choose you over someone else. You don’t have to be a Madison Avenue marketer to build a powerful brand. You have to connect with people, stay authentic, and deliver consistently.
When I read the stories of these entrepreneurs, I saw reflections of my own journey — putting ideas into the world without a perfect plan, only to discover that what resonated most with people was often the raw, human side of it. Vinjamuri shows that accidental branding isn’t really accidental at all. It’s the natural result of passion, persistence, and listening to your audience.
This book shifted my perspective. Instead of stressing about whether my branding was polished enough, I started asking whether my brand felt real enough. Because in today’s marketplace, authenticity beats perfection every single time.
9. Curation Nation: How to Win in a World Where Consumers are Creators by Steven Rosenbaum
This book was ahead of its time. Rosenbaum explains how curation — selecting, organizing, and adding context to existing content — is just as valuable as creating original material.
Back when I first read it, I realized I didn’t have to reinvent the wheel with every piece of content. I could curate, frame, and contextualize, and that was just as powerful. In today’s noisy world, the ability to curate well is a true advantage.
The stories are practical and inspiring, but what makes this book special for me is that I actually interviewed Steven Rosenbaum years ago during my Squidoo days for a lens I created. That experience made the lessons stick even more because I could see how much thought went into what seemed like “accidental” success.
10. The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss
This book has become a cliché in some circles, but there’s a reason it’s still recommended. Ferriss challenged the idea that you have to trade time for money forever.
What I took away wasn’t the idea of only working four hours a week (let’s be real, I enjoy my work too much to step back that far). It was the principle of designing a business that gives you freedom and flexibility. Outsourcing, automating, and prioritizing the right things are all part of the toolkit.
Wrapping Up
These ten books are very different from one another, but that’s exactly why they belong on this list. Entrepreneurship isn’t just marketing and sales. It’s learning how to think creatively, manage your time, overcome resistance, and build a brand that reflects who you are.
Some of these books will hit you at just the right moment. For me, The War of Art got me moving when I felt paralyzed, and Curation Nation opened my eyes back in the Squidoo era to the power of being a curator, not just a creator.
If you’re serious about growing your business, start working through this list. Each book is a window into a different way of thinking — and the more perspectives you add, the sharper your entrepreneurial instincts will become.
Tiff 😉
