Best Books for Entrepreneurs

We are multi-dimensional people. What we learn and do in one area of life can enhance what we accomplish in others.

On any given day, we might administrate, create, innovate, meditate—basically, we wear a lot of hats in the hope that on the whole, we’ll have a happy and meaningful life.

But if we spend too much time doing and not enough time resting, reflecting, and planning, we may become unknowingly submissive to the ideas of the dominant culture and toil away the best of ourselves preserving a status quo we never set.

Take a moment to schedule a stay-cation and invest some time in yourself with these books. Even if it takes you seven years to read these seven books, it’s well worth it!

Do the Work, by Steven Pressfield

Overcome Resistance and Get Out of Your Own Way (2011) | Anything worth doing over a span of time is going to present you with Resistance. It gets a capital “R” because it may be the most substantial force you’ll ever experience in life and work. While the book makes references to being a writer, Steven is emphatic that it doesn’t matter what your chosen endeavor is—the concepts apply to everything. When you find yourself feeling fearful, when you self-sabotage or self-doubt, and when you procrastinate, this book is the antidote. I enjoyed the audio version. Learn more. Watch Steven talk with Oprah.

Winning, by Rob Cummings

The Five Truths of Fundraising (2019) | In 2014, I was doing a fundraising internship at a land conservation organization in Chicago, Illinois when a colleague recommended Rob’s weekly e-newsletter to me. Since then, he wrote a book that distills all of the wisdom he learned in four decades of professional fundraising. Why choose a book about fundraising for this list? Because the principles he conveys apply to any endeavor where you’ll need to build relationships and grow your network. I enjoyed the audio version of the book. In 2020, I was honored to build his new website.

Lean In, by Sheryl Sandberg

Women, Work, and the Will to Lead (2013) | Until I graduated from college, most of my employment was led by men. After college, I was fortunate to spend a decade working in nonprofits where women were more likely to lead. At a women’s leadership group organized by the local chamber of commerce, we started reading Lean In. By the end of that year, I had decided to chart a new course in my professional life. Sheryl prompted me to reflect on my experience as a woman in the workplace and she inspired me to hit the reset button on my career—not to leave it, but to change it so it worked for me instead of against me. The paperback version of the book was perfect for underlining passages and making notes in the margins. Learn more. Watch Sheryl’s TED Talk.

Quiet, by Susan Cain

The Power of Introverts in a World that Can’t Stop Talking (2012) | If anyone suggests you need to change who you are to be successful in your endeavor, stop listening to them. Start listening to Susan Cain instead. You can trust her to be honest about personality styles, historical people, and when it makes sense to emulate extroverted behavior to achieve a certain goal. It’s possible to demonstrate great people skills and celebrate your introversion. While extroverts chat away at the water cooler, introverts create beautiful things and build reliable businesses that stand the test of time. I enjoyed the audio version of the book. Learn more. Watch Susan’s TED Talk.

Hillbilly Elegy, by J.D. Vance

A Memoir of Family and Culture in Crisis (2016) | This one doesn’t appear to be relevant to business, or is it? If you came from meager beginnings and took on the challenge of advancing yourself despite all odds, J.D.’s story will help you make meaning of it and inspire you to keep going. Hillbilly Elegy was recommended to me by a fellow college alumnus at an 2017 reunion event. The story helped me spot a common thread in our lives as people who got out of “the hollar” to achieve an American Dream. It also prompted me to think deeply about complex social problems without easy solutions that deserve more attention. The movie was due to be released in November 2020. I enjoyed the Kindle version of the book. Learn more. Watch J.D. on Face the Nation.

Inside the Box, by Drew Boyd and Jacob Goldenberg

A Proven System of Creativity for Breakthrough Results (2013) | How many times have you heard that the most creative people are those who think outside the box? If you’ve done it, how often did you get feedback from others to get back inside the box? Confused? I was, too, until I listened to Inside the Box. There’s a way of thinking systematically to improve products and services that actually fosters creativity instead of restricting it. As a characteristically fixed thinker, I developed the ability to create programs, raise money, and reduce overhead in nonprofits, but the concepts apply to innovations in art and business, as well. This book reinforces how to think to get the results you want. I recommend the Kindle version of Inside the Box, plus Drew’s LinkedIn courses on marketing. Learn more.

Content Marketing for Nonprofits, by Kivi Leroux Miller

A Communications Map for Engaging Your Community, Becoming a Favorite Cause, and Raising More Money (2013) | There’s a difference between promotion and marketing. Do you know what it is? Your art, business, or nonprofit can benefit from developing a cause as a part of your brand. Making sure your marketing stays on-brand no matter how many people contribute is a challenge, too, but Content Marketing for Nonprofits can help. This book will help you avoid empty sales and promotional tactics to build loyalty and trust with your audience. I enjoyed the paperback version of the book. Learn more.