Every year, we have a nine-month program to bring entrepreneurial parents together for an extended period of time together—it’s like a community meets a retreat-like virtual space. We get to know each other, go deep on personal growth and business growth questions, and navigate the maze that is parenting and business. It’s not easy, but it’s way better than going it alone.

We meet twice per month—more if you sign up for the group coaching add-on—and each month, we have a new book pick in our book club. The book club is optional, and I ask everyone to pick their top three books to read each year and join in on the Slack channel to discuss the book of the month. Why is it optional? Because you’re an entrepreneur and a parent! We don’t do a book club like other folks do book clubs—read more about our philosophy and approach here. In short, we don’t give you homework and make you feel bad for falling behind. Instead, we host awesome conversations that you can join whenever you are able to, and if you have to skip a month, it’s all good.

Last year’s books were SO good and the conversations were even better. From figuring out how to do less, to learning about the rage-inducing amount of household labor that holds women back, to reading boss leadership books like Dare To Lead and Radical Candor, we stepped up last year and improved out cultural knowledge, our leadership capabilities, and our business prowess.

Here’s a sneak peek at the entrepreneurship and leadership books we’re finalizing for our 2020 book club.

They correlate to our monthly themes and are focused on expanding your mindset, personal leadership, and business prowess. We’re still finalizing a few of the books and will take a vote once everyone applies and we have the group all together!

Take a look and I’d love to know from you: what books have you read that have made an impact on your entrepreneurial or leadership journey? Leave a note in the comments!

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The 2020 Wise Women’s Council — Our Book List for Entrepreneurs, Leaders, and Parents

Playing Big: Practical Wisdom for Women Who Want to Speak Up, Create, and Lead, by Tara Mohr.

Tara Mohr is the mother of two children, a Stanford business school graduate, and the Founder of Playing Big, a leadership program and training for women. I’ve read her book several times and am planning to interview her for the podcast—her voice and leadership is so important for women who are growing businesses and who feel called to step into leadership positions. We’ll kick off the first month examining leadership and our call to live bigger lives from where we are. Dream big.

Buy this book on Amazon.

The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail (Management of Innovation and Change), by Clayton M Christensen

Considered one of the best business books of all time, this book is a classic primer on innovation and disruption, and what you need to know for your business to work not just today, but for as long as possible. What does innovation look like in a world rapidly changing by technology? What firms are closing? What lessons can we learn for our own businesses? This book will challenge us to think through innovation more broadly as well as within each of our own business ventures.

Buy this book on Amazon.

Tell Me More: Stories About the 12 Hardest Things I’m Learning to Say, by Kelly Corrigan.

This book captivates and moves—a series of essay-based stories about the challenging moments in life, and the things you learn to say as a caregiver, parent, daughter, and friend. From listening to your pre-teen tell you what’s on their mind and biting your tongue in order to say “Tell me more,” to understanding how to say no, to learning to leave your loved ones behind, this book is a primer on the hard things.

Buy this book on Amazon.



The Confidence Code: The Science and Art of Self-Assurance—What Women Should Know, by Katty Kay and Claire Shipman

What does it take to grow into the next level of yourself as a leader and a mentor? For women in their 30s and 40s, facing parenthood can be a devastating setback to self-confidence and self-assurance. In the throes of sleep deprivation and wondering how the heck you’re going to manage your life with kids, finding your way back to confidence and self-assurance is a must. This book will be our primer for making the most of these years, and how to recreate our own assurance and leadership despite the chaos that’s happening all around us.

Buy the book on Amazon.

Company of One: Why Staying Small Is the Next Big Thing for Business, by Paul Jarvis.

In a world that tells us to grow fast and scale faster, and that unicorns are the only companies worth profiling and emulating—what other forms of business exist? For us here at Startup Pregnant, we want to reclaim the idea that entrepreneurship comes in a whole host of flavors and paths. From the small business owner to the self-funded company, to the startup team building with focus and consistency, building a company can look like a hundred different things. Rather than build a 100-person ship that you despite managing, build a company that best fits you as a founder. This book will challenge us to rethink what a company must look like, and how it can work.

Buy this book on Amazon.

Another book contender for this month’s theme of leadership is The Startup Way, by Eric Ries. We’re leaning towards Company of One, because the message is a little more provocative.



Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine, by Michael Michalowicz

Everyone I know raves about this book—and for good reason. So many businesses boast of their gross revenues, or their team sizes, or their Instagram followers—but at the end of the day, the bottom line doesn’t pan out. I know far too many businesses that have grossed over a million dollars, but the profit margins are so slim, the founders are barely making any money. A business exists to serve customers, solve problems, and make money. That profit part is important. We’ll read this to focus on revenue, talk about money, and find your paths to profitability.

Another contender for this month’s theme on business growth is The Messy Middle, by Scott Belsky.

Buy the book on Amazon.

Invisible Women: Data Bias in a World Designed for Men, by Caroline Criado Perez

What is the cost of being a woman? This book is a detailed and devastating account into the way that data bias—and ignorance—costs women their lives on a regular basis. From iPhones that are too large for women’s hands (making it harder to call for help in an emergency), to women who are killed in car accidents because air bags and seat belts are designed for men as a default, to hundreds more examples, women’s lives and livelihoods are often at risk because of the way we use numbers and data and assume male as a default norm. Engaging and provoking, Criado Perez makes an important case for rethinking our baseline assumptions. She writes, “Because so much data fails to take into account gender, because it treats men as the default and women as atypical, bias and discrimination are baked into our systems. And women pay tremendous costs for this bias, in time, money, and often with their lives.”

Buy the book on Amazon.

Boys & Sex: Young Men on Hookups, Love, Porn, Consent, and Navigating the New Masculinity, by Peggy Orenstein

Last year, we looked at our partnerships and the relationships we cultivate in our marriages and dating lives—this year, I want to bring attention to the relationships we have with our children, and how our children’s relationships will change and grow as they mature into pre-teens and teens. When I read Girls & Sex, I was blown away by the information on how girls grow up and their sexuality, and I’ve been waiting for this book to come out since I heard that Peggy Orenstein was writing a second book. We’ll talk about our children, sex, relationships, and their development into adolescents—and what we need to know as parents.

Buy the book on Amazon.

Let Your Life Speak: Listening for the Voice of Vocation, by Parker J. Palmer.

What happens to us in our thirties and forties—sometimes sooner, sometimes later—is that we run into a crisis of confidence, direction, or meaning. So many women and men that I work with find themselves at a crossroads unexpectedly: their company isn’t what they thought; they’re ready to leave and start something new; something has crumbled; their passion has faded. How do you find space to listen to what your life is calling for, and transition to the next project, purpose, or calling? Parker Palmer is kind, thoughtful, and soulful, and has written books on finding your way when you feel lost. This book will help us navigate where we go next, when next feels murky and unclear.

Buy the book on Amazon.

We’re almost done finalizing the book list, but while we make the cuts, the following books are also contenders for our reading list:

We’re thrilled by these books and can’t wait to dig in and discuss them. If you’re signed up for The Wise Women’s Council, we’ll meet monthly for our book club, and you can join any and all months you want to join. (Remember, our book club is a non-traditional book club and you don’t have to make every month; it’s optional for the books or months you want to join in! Read more about how our book club is different, here.)

PS: If you’re joining the Wise Women’s Council while you’re pregnant or in the early postpartum period, you get a different book list.

Several people join us when they’re pregnant or expecting, and find that different seasons of life (like the first trimester, or the fourth trimester!) make additional book reading incredibly challenging. If that’s the case for you, I highly recommend that you stick with just a couple of books that are tailored for you and your immediate needs. You can join our book club and listen in, and read when you have the time (I read a surprising number of books while breastfeeding!).

Books for the early postpartum period: The Fourth Trimester, The First 40 Days, and The Fifth Trimester.

What are your favorite books? What books would you recommend for new parents, entrepreneurs, or for building into the next phase of your business? Leave a note in the comments!