8 Books That Taught Me How To Run a Small Business in My Twenties

Starting a business in your twenties can feel like building a plane while you're mid-flight. When I started Creative Kind at 22, I didn’t have a degree in business or any formal experience.

What I did have was a willingness to learn, the grit to keep going when things got tough, and an endless stack of small business books. They became my lifeline, offering ideas, strategies, and some much-needed reassurance along the way.

Looking back at 32, there are 8 books that stand out as game-changers for me. They helped me refine my approach to business, improve how I lead, and find balance in the chaos of entrepreneurship. Whether you're just starting your own venture or are deep in the trenches, these books will inspire and equip you to take your business to the next level.

1. The E-Myth Revisited by Michael E. Gerber

If you only read one book about entrepreneurship, make it this one. Gerber strips away the myth that successful small business owners "do it all" and instead explains why systems, not superhuman effort, create sustainable and scalable businesses. This book completely shifted how I approached Creative Kind—from trying to wear all the hats to building processes that allow my business to run smoothly (even when I'm not in the room).

Key takeaway: Work on your business, not just in it.

2. The Small Army Strategy by Srinivas Rao

This book is all about the power of building a loyal community instead of chasing vanity metrics. Rao’s advice is particularly useful for startups and niche businesses (like Creative Kind!). His focus on deep, meaningful relationships over shallow attempts at “growth” resonated with me deeply—and helped me see the value in the community we cultivated through our workshops and stores.

I started Creative Kind by individually messaging folks an invite to our first workshop way back in the day. Many of those people are still friends and supporters today.

Key takeaway: Your small, dedicated army of supporters can be far more impactful than a massive, disconnected audience.

3. Marketing: A Love Story by Bernadette Jiwa

Marketing doesn’t have to feel icky—and Jiwa proves it. She reframes marketing as an act of love and service, focusing on building genuine connections rather than shouting into the void. If you’re struggling to figure out how to authentically market your business, this book will feel like a breath of fresh air.

Key takeaway: Marketing is simply helping people solve problems they care about—lead with empathy.

4. Crucial Conversations by Kerry Patterson

Business is relationships, and relationships are built on communication. This book provides practical strategies for handling high-stakes conversations with confidence and clarity.

Having the hard conversations is honestly one of the most challenging parts of running a business. From negotiating leases to managing employees, the lessons in Crucial Conversations have been invaluable in helping my manage my own anxiety and approach tough situations with clarity and grace.

Key takeaway: The most important conversations often feel the hardest—approach them with preparation, empathy, and an open mind.

5. Traction by Gino Wickman

This book introduced me to the Entrepreneurial Operating System (EOS), a framework designed to help businesses run like well-oiled machines. Implementing EOS helped me set clearer goals, stay organized, and achieve more with my team. It’s practical, actionable, and doesn’t waste a single word.

Key takeaway: Break big goals into smaller, measurable steps—and stay focused.

6. Profit First by Mike Michalowicz

Managing money as a young entrepreneur is tricky (and often overwhelming).

While it took me a few false starts to dig into it, this book completely changed how I think about business finances. By flipping the traditional accounting model, Michalowicz helped me prioritize profit and create a more sustainable financial plan for Creative Kind.

Key takeaway: Pay yourself first—profit isn’t just what’s left over.

7. Creativity, Inc. by Amy Wallace and Edwin Catmull

Written by the co-founder of Pixar, this book dives into the intersection of creativity and leadership. It's packed with lessons on how to foster innovation, create collaborative teams, and build a company culture that thrives. This book helped me avoid burnout during the hustle years and reminded me to keep creativity at the heart of everything we do at Creative Kind.

Key takeaway: A great leader cultivates an environment where creativity can flourish.

8. Unreasonable Hospitality by Will Guidara

This is one of the most human, heartwarming business books I’ve read. Guidara, the former co-owner of Eleven Madison Park (one of the world’s top restaurants), shares how going above and beyond for customers creates unforgettable experiences. It's a philosophy that's supported my drive to add extra touches to every interaction we have at Creative Kind, from personalized customer service to thoughtful product packaging.

Key takeaway: Small gestures can have a big impact—never underestimate the power of kindness.

Why These Books Matter

Each of these books taught me something important about running a business. Some provided frameworks and methods I still use every day, while others gave me a fresh perspective during tough times. Most importantly, they reminded me that I’m never alone in this entrepreneurial journey—there’s always wisdom to be found if I’m willing to look for it.

Running a business will always involve trial and error. But with the right resources (and a lot of curiosity), you’ll find the knowledge and confidence to keep growing.