Back when I was still a cubicle-dwelling 9-to-5er—snoozing my way through conference planning meetings and writing up catalog copy—I began to suspect that there might be an alternate path for me. And while I didn’t necessarily think of myself as an aspiring entrepreneur, I did know that I wanted to spend my days creating, answering to no one but myself.
Before jumping ship, however, I prepared myself. I took continuing education classes. I started working a second job in the evenings on a freelance basis, until they were able to offer me more hours. I lined up several more clients, and even got my present employer to sign on as a client when I finally handed in my letter of resignation.
And I read books. Oh, so many books. The best books for aspiring entrepreneurs…or something…that I could find.
Within a year of leaving my full-time job, I had matched my previous salary. Eventually, I started a blog for those who might want to do something similar. I became a founding member of the Young Entrepreneur Council. I tried a lot of things, and I failed at some of them, but I succeeded at others. I continued reading books and I continued getting better at this whole being-your-own-boss thing.
Today, I’m pretty happy with where things are. I juggle writing, editing, and motherhood and, while it’s tough, it’s still awesome. I even have a book on the way, which was a dream of mine even before I started working my way up the corporate ladder. My life is fulfilling, flexible, and completely my own.
If this sounds at all attractive to you, and if you’re also an aspiring entrepreneur, I suggest you read as much as you can, too. Because, for me, taking the time to educate myself before upending my career made all the difference in the world.
To that end, here are the 10 best books for aspiring entrepreneurs to start you on the path to kicking butt and wearing elastic-waist pants all day.
1. Michelle Goodman’s The Anti 9 to 5 Guide
This is the first book that opened my eyes to the fact that the traditional, college-to-corporate-ladder pipeline might not be the only option out there. And while Goodman doesn’t focus on how to launch a business—instead spending her time talking up side gigs and flex jobs—she does share a lot of good information on transitioning out of a traditional, full-time job, managing money, and monetizing one’s passion. She later wrote My So-Called Freelance Life, which contains even more information on writing a business plan, making your company official, creating a budget, and more.
2. Lauren Bacon and Emira Mears’s The Boss of You
This book is more overtly about being a young, female entrepreneur, and I love it to death. As I became more business-minded in those early days, I benefited greatly from its lessons on figuring out your specialty, researching the competition, being able to pivot, budgeting, marketing, branding, networking…how much corporate speak can I fit into one sentence? I’ll ping you later when I figure it out.
3. Ramit Sethi’s Your Move
Sethi is best known for his best-selling I Will Teach You to Be Rich, but its successor is all about building a business from scratch. In it, Sethi writes about conceiving of a business idea that will actually be profitable, finding customers, automating your business so as to build in passive income streams, and more.
4. Chris Guillebeau’s The $100 Startup
Around the time of the 2008 financial crisis, a time when I was all, “Oh shit, I have to pivot!” and entrepreneurial gurus and career coaches were crawling out of the woodwork in droves, I started seeing Guillebeau’s name everywhere. He’s since written four hugely popular books about personal development and entrepreneurship, but this one in particular shows readers how to get paid to do what you love, draw up a one-page business plan, self-promote, raise funding and, in the end, succeed no matter what.
5. Guy Kawasaki’s The Art of the Start 2.0
Kawasaki also cashed in on the newly emerging, necessity-born gig economy—but who could blame him? He certainly had the cred, with his experience as a chief evangelist at Apple, and his later work founding several small businesses. In The Art of the Start, he takes aspiring entrepreneurs through the entire process of creating a startup, from conception to bootstrapping and fundraising to enduring.
6. Kevin D. Johnson’s The Entrepreneur Mind
Johnson also has strong credentials. He was a serial entrepreneur for many years, and eventually founded the wildly successful Johnson Media Inc. His book is intended to help readers to develop the same mindset as other thriving entrepreneurs, one that allows them to think big, captivate investors, and more.
7. Pamela Slim’s Escape from Cubicle Nation
Another book I read back in the day was this one, for those still trapped in that terrifying cubicle maze. Although I had long since left my own cubicle, Slim’s book aided me in reevaluating my business plan, making new annual revenue targets, and continuing to kick ass.
8. Joy Deangdeelert Cho and Meg Mateo Ilasco’s Creative, Inc.
I became a fan of Cho’s back when I was managing a products blog for Nerve. She was the talented woman behind the design blog Oh Joy! So when Creative, Inc. pubbed in 2010, I was ready to do whatever she told me to do. Cho and Ilasco’s book is intended for creative freelancers who are looking to build a successful business doing what they love. It includes all of the good, meaty info you want in a business book, such as business plans, branding and publicity, dealing with clients (god, yes), getting paid, and more. I also appreciated its inclusion of a chapter on balancing your business and personal life.
9. Danielle LaPorte’s The Fire Starter Sessions
Several years into the financial downturn, we were all drowning in gurus, ninjas, and rock stars, and I had lost my patience for all of those “Follow your dreams! Success will follow!” blog posts. Because while they all crowed about the importance of following your passion, too many of them didn’t tell readers how to turn their passion into a feasible business model that would enable them to survive. LaPorte uses words like radiance and devotion and illumination, so I was wary, but she also uses worksheets, and I fucking love worksheets. Her Fire Starter Sessions has SO MANY WORKSHEETS on figuring out your superpowers and deconstructing fear and figuring out your support team and, you know what? We need that. We really do.
10. Dale Carnegie’s How to Win Friends and Influence People
Finally, I present to you this classic (first published in 1937), which has been reissued a gajillion times, and which has sold eleventy billion copies (okay, that’s an estimate), and for very good reason. It’s one of the best books for aspiring entrepreneurs. At its core, it’s about networking which—more than anything else—is the not-so-secret secret to my success. As I’ve moved through life, from job to job and client to client, it’s the connections I’ve made that have continued pushing me onward and upward. Which is no small feat for an awkward, socially anxious, introverted recluse who doesn’t like to put on anything without an elastic waistband. So I suppose you could credit the lessons in this book for some of my success. That and I’m surprisingly lovable.
So that’s my syllabus of the best books for aspiring entrepreneurs. Which books catapulted you to greatness?
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