“I'm sorry, but I just can't come back.” I had mulled over what to say and how to say it for days. However, having the conversation with my boss was not any easier for having thought it through. I got off the call hoping I had done the right thing, as I felt a mixed range of emotions wash over me: guilt, relief, and a touch of anxiety. I took a deep breath and walked down the hallway of my apartment and stopped to lean over the crib of my 3-month-old, who was sleeping, entirely unaware of the decision I had just made.

I had agonized over childcare options for months. I wasn't entirely sure of what the right thing to do as a new parent was, but I knew I didn't want to get it wrong. All the data I could find on early childhood development pointed to the importance of an individual caregiving experience and the critical nature of the parent-child bond. I wasn't willing to risk my baby's development, so I quit my job - putting my own career at risk in the process.

I know this sounds dramatic. But the whole experience of becoming a new mother was dramatic for me as a 27-year-old with a fledgling career, living in a fourth-floor walkup, railroad apartment in New York City. I, like many other women, thought deeply about the role I was taking on, and obsessed about getting it all right, sometimes to my own detriment. And frankly, my body was a mess of stretched skin and fluctuating hormones, so even after three months I didn't feel physically ready to return to work, either. So, I made that call to my employer to let him know that I wouldn't be coming back, and stared into the eyes of this small human, determined to take my new role seriously. A year and a half later, my husband and I went on to have another child, and I continued my responsibilities as a stay-at-home parent for years. But after some time, as my kids got a bit older, I wavered in my decision to give up my professional pursuits. I knew I wanted and needed to contribute more financially to our family.

Shortly after the birth of our second child we made the move so many make to the suburbs. In our case, we'd also taken on a complete renovation project of a historic house. But my options for workforce reentry were scarce. The gap on my resume looked like just the word sounded—a gap in ambition—not a purposeful plan I had crafted to focus on personalized learning and caregiving in partnership with my husband. My volunteer roles as a library board director, and the skills I'd developed researching, managing, and in some cases implementing renovation projects, did little to externally enhance my resume. I quickly realized that any step I took back into the workforce would likely be a step back from where I had left off and would still create logistical challenges. So, I explored other ideas, and I identified some opportunities in the low-tech environment I had entered as a parent, which contrasted sharply with the high-tech environment in which I had previously worked. I saw an opportunity for a business.

I went on to start a software company, be the CEO, raise capital, provide value to customers, sell the business, lead a division within a billion-dollar company, and be recognized as a “Woman to Watch in Tech” by the Boston Business Journal and as a “ChangeMaker” by HUBWeek. I became a board director of a private equity–backed company, a managing director at a world-class investment firm, and in addition, I think I'm a pretty engaged mom to my now-teenaged boys. Although this was not a straightforward or easy path, I don't think it would have been possible if I had stayed on a traditional career path.

By starting my own company, I was able to gain a set of experiences that are difficult to get in a silo-ed organization, and I was able to do it while more fully integrating my work into my life. I made these decisions several years before Sheryl Sandberg's book Lean In was published, and a decade later the conversation on women and work has still not quieted down.

As I made decisions throughout my journey, I was reacting to the existing framework of what I understood to be possible. While my journey may sound unique, the choices that I felt I had at the time are common, and they are based on a history that hasn't really considered women in the workplace from the lens of what's possible.

How Did We Get Here?

In early 2019 former U.S. first lady Michelle Obama, who I greatly admire, made a passing comment while on a book tour in New York, simply noting that “lean in” doesn't work all of the time. Her casual remarks unleashed a firestorm of debate. Dozens of media outlets, including The Guardian, Fortune, Newsweek, NBC, and the Washington Post all ran with the story. Headlines screamed “Michelle Obama Slams Sheryl Sandberg's Lean In Theory!” “Michelle Obama Believes Lean In Doesn't Work!” It was as if the collective voice of the predominately male-owned media had reared its head to seize hold of any conversation on the topic of women in the workplace to say, “I told you so! You really can't have it all—even Michelle Obama agrees!” And knowing that, as the New York Times reported in 2018, 86% of all women become mothers, it was no wonder that the topic quickly added to the national dialogue. But as I read the stories and listened to the ensuing heated discussions that unfolded on whether women could really have it all, I had a different thought. I thought, “Yes, you can…but not like this.”

Like millions of other people, I read Sheryl Sandberg's 2013 book Lean In and was motivated by it to rethink many social norms I had long unconsciously accepted. Her book, which encourages women to double down on their careers and assert their leadership skills, inspired me to continue to move my business, which I had started after stepping away from the traditional corporate world for a few years to be with my young children, forward. In fact, I was so inspired by Lean In that I was profiled on the Lean In website as a case on “Taking Risks” in 2013 (https://leanin.org/stories/claudia-reuter). However, I also understand why many people argue that leaning in doesn't work. The book has managed to be a part of a national conversation for more than six years, and there are myriad reasons why one could argue that leaning in, in it's most basic interpretation, is unrealistic. Yet, I don't think it's the act of leaning in that doesn't work. It's not the pursuit of meaningful work or the desire to lead, and earn a meaningful wage, that doesn't work. It's the structures into which we're leaning, even with a goal to change them, that make it look so difficult.

Many corporate structures are rooted in a past that no longer exists: single-earner, male, and ethnically homogeneous. As Marissa Orr describes in her 2019 book Lean Out, “Our systems must evolve, and until they do they're leaving a treasure of diverse talent on the table.” One solution Orr offers is to “recognize the limitations of the system in which we work and understand that it cannot always fulfill our deepest human needs… When we recognize that we're looking for satisfaction in all the wrong places, the pain of our jobs begins to release its grip, and we can find alternative ways to fulfill our needs.” In Lean Out, Orr candidly describes her experience of parting ways with Facebook. In her book, she dives into research on whether women even want the leadership roles that Sandberg rallies for women to go after, and offered statistics showing that, in fact, very few women or men want to be CEOs or high-level managers. Instead, she advocates for directing dollars toward supporting women in lesser positions and dropping the focus on getting more women into leadership positions within today's corporate structures. I understand her point, as well as the media frenzy that followed Michelle Obama's comment. However, I think this is a false dichotomy.

Rather than debate whether women should lean in or lean out, why not offer an alternative, one that empowers women and men to redesign the very structures that are broken and to build the lives they want right now?

Why Not Lean In by Starting Up and Move Past the Binary Setup?

Many women jumped deeply into their careers following the success of Lean In and its affiliated groups or circles, of which I'm also a member. Speaking with a number of recent college graduates at a university alumni event earlier this year, I heard first-hand how the impact of Lean In's success, coupled with the current college student-loan crisis, has left many younger women stressed and anxious, wondering how they will blend the careers they've prepared for and the families they may want someday. And the backlash that has erupted against Lean In actually reinforces the idea that we are all somehow choosing between “work” and “family,” choices that, as Tina Fey famously called out in her book Bossypants, men are seldom—if ever—asked to make. The implication in creating a dialogue on leaning in versus leaning out is that it allows the myth to persist that those are the only two options. The message is an either/or, binary proposition: either we work with what exists today or we step away from our passions or desire to lead. I don't think that was Sandberg's intention when she wrote Lean In. In fact, she called out how women should work to adjust the system, and to hold men accountable as partners as they lean in to careers.

But by setting up a “lean in versus lean out” dialogue in our society, we are reinforcing a dichotomy in which other options don't really exist. And it's true that for those without an MBA or law degree, or a supportive partner, or the income to support a full-time nanny or childcare provider, there is no real option to lean in to today's corporate environment with any expectation of career progression. The invitation extended by today's corporate environment, in which only 17% of companies even offer a few weeks of paid maternity leave, let alone provide flexible working environments, is to simply get through it. Office hours seldom align with school hours, forcing parents to work part-time, work after-office hours, or seek childcare. The cost of childcare alone can be as high as university tuition—tens of thousands of dollars per year. The idea of getting through it, that you can (or should) just suffer through a few years of high-cost childcare before the public school system doors open is unacceptable. The idea that the bump in your 401K and potential career advancement will make the long days with paltry take-home pay and sleepless nights easier is also unacceptable. And the idea that the extra effort required to externally appear to make it all look easy is worth it is untenable. I can't think of many people who are motivated and inspired by compound interest or the potential for a promotion alone.

But it's also just as true that you can't comfortably lean out without a supportive partner or the income to support a part-time or single-earner lifestyle. Many people who step away from the workforce are doing so by cobbling together savings and looking for discounts to simply make life feel somewhat comfortable. The structures that are in place make it challenging for people who are primary caregivers to stay in an organization because they were not designed for caregivers. They were designed for people who already have support—child, family, parent. That's why approximately 43% of women leave the traditional workforce at some point in their careers. And even if they do reenter the traditional workforce, they are usually offered positions at lower wages from when they left. That wage and time gap then partially explains why there are fewer women in leadership positions, and why only a small percentage of Fortune 500 companies or corporate board members are women. I think it also helps explain why, in 2019, we still don't see a large percentage of men willing to take on the role of primary caregiver, because even our societal views of caregiving itself are often binary. There is a tendency to view women (and men) who opt out of the traditional workforce to care for children as either wholly unambitious or, conversely, worthy of being put on a pedestal for modeling excellent personalized caregiving and upholding the romantic ideal of motherhood. Likewise, a recent study from the Pew Institute showed that only 8% of respondents thought that having a father home was beneficial, whereas 76% responded that fathers should be at work. As Susan Magsamen, executive director of the International Arts and Mind Lab at the Brain Science Institute for Johns Hopkins University, pointed out on my podcast The 43 Percent in 2019, “We pay for what we value, and we don't value childcare, we don't value early childhood education, and we don't pay for it. It's what women do.”

So we have systems in place that encourage us to believe that the option before us is to lean in to a career while tending to the task of parenting quietly and unseen, or to publicly lean out, essentially giving up our claim to the monetary benefits that enhance our well-being in our capitalist society. In both scenarios we acknowledge that caring for children needs to happen, but, as Magsamen articulated, we don't value it financially. It's worth noting that at various points in this book, I call out how the high price of childcare can consume a large percentage of your take-home pay and factors into the decision to lean in or lean out. The not-so-subtle additional point here, though, is that the “high price” is not often more than your take-home pay. If it were, more people would actually look to become childcare providers to earn a decent living. Instead, childcare is just expensive enough to cause challenges for those not yet earning a six-figure salary, but low-cost enough to be insufficient to provide for a high quality of life for those who pursue it as a profession.

The Privilege of Being in Charge

As I reread Lean In in 2019, the chapter called “The Myth of Doing It All” caught my attention. In that chapter, Sandberg suggests that, with the advent of technology, employers can shift to “focusing on results [which] would benefit individuals and make companies more efficient and competitive” rather than judging time at the office. The central idea is that many of the constraints that women face are related to time management and the structures that were put into practice without having the whole person in mind. Sandberg recalls a time when she adjusted her schedule to have her first and last meetings of the day at another facility so she could see her child before and after work without other employees noticing. To her point, she wasn't working any less; in fact, she was working more. But in her mind there was a stigma associated with simply appearing to shorten her workday, especially because it was in an effort to see her child. That stigma is the shadow of the existing corporate walls. By sharing that story of hiding her schedule, Sandberg not only identified one of the main challenges parents, and, in particular, moms, have in the workplace; she also highlighted the privilege she had in making that decision, a privilege that those lower on the career ladder seldom have. It's no wonder her book has become as divisive as it is inspiring.

It was with similar outrage that people responded to stories of Yahoo's first female CEO, Marissa Mayer, setting up a nursery for her new baby in the office. As The Guardian pointed out, some were upset that she was taking such little time off, while others were frustrated that she had to talk about it. The lean in or lean out debate is really a critique of how women behave in a workforce that was never designed with them in mind and hasn't put a high financial value on caregiving, despite the relative high cost to families. I highlight so much backstory on women as mothers (which is not to say that all women will or should become mothers) because 86% of women do become mothers at some point, and they often become mothers just as their careers reach a critical inflection point. Most people with college degrees who follow a traditional career ladder reach the point of management or directorship during their early 30s, approximately 10 years into their careers. This, of course, is also the exact time that many women and men look to start families. According to a recent study from the New York Times, while the average age at which a woman has her first child is approximately 26, the average age that a woman with a college education has her first child is now 31. And that age is consistent across the United States, whether she is in Missouri or New York City.

So Let's Get in Charge and Lean-in to Entrepreneurship

There's an option that empowers women to lean in, not to the systems and corporate structures that others created long ago, but to the new systems we can create today. What if we elevated the conversation by encouraging more women to enter entrepreneurship? I write this not in an attempt to put more pressure on people or make people feel more frazzled. I can already hear people saying, “But startup life is known to be stressful—now I have to figure out how to manage that as well?” That response is a by-product of trying to work with corporate systems and structures that really haven't been around that long and certainly were not designed with both men and women in mind. Consider that less than a century ago, when many of the current leaders of Fortune 500 companies, U.S. Senators, and House Representatives, were young adults, employers were still able to discriminate based on gender and pregnancy. Since fighting for and achieving the right to vote in 1920, women have continued to lobby and push against the existing systems, making large and small advancements along the way. But the underlying thread is that we're asking for permission from the existing patriarchal setup. Consider again that it wasn't until the 1970s that a woman could even easily obtain credit without a male co-signer. The implications of this, of course, were that it was incredibly difficult until very recently for a woman to obtain a credit line to attempt to start her own business or to buy property. With that in mind, it's easy to understand how it was also culturally empowering for women to actually remain focused on the path of supportive wife to a successful partner, rather than focusing on career ascension or entrepreneurship. And while that ability to obtain credit was certainly progress from achieving the right to vote, more than 50 years went by between the two events. According to research from the World Economic Forum, at our current pace, it will take 170 years to achieve gender parity in the workforce.

This slow-moving drive to equity is mounted against much of the corporate schedule and formulated workweek we currently take for granted and are simply by-products of the shift to mass production that happened before the advent of modern technology and the internet. The beauty of a startup is that you create value in the economy and you also control your day. When you start a business, you are automatically in a leadership position. You don't need to wait in line, and you get to make the decisions that are best for the company, including structures such as office hours, location, and other policies. You have the freedom to create the business you want and to build the life you want at the same time. As new startups are formed, they rarely look like traditional companies. They often have flexible schedules, unlimited vacation, bring-your-dog-to-work options, casual dress, and other more modern policies. And although many don't succeed, many startups have disrupted traditional businesses in ways no one could have imagined earlier. Consider that according to a study by “Innosight,” which Harvard Business Review referenced in a 2017 article, by 2027, 75% of today's Fortune 500 companies will be displaced. So why not start to build a company that could be on that list of disruptors, and create a new set of structures in the process? I am confident that we can convert the debate into a conversation that promotes more than the either/or choices most people believe they're limited to, by encouraging and supporting women to start up as another alternative. By starting up you can build the life you want, with the rules that work for you, and this book will show you how. (Exciting, right?)

Win or Lose, How Do I Know You Can Do This?

Why This Book Is for You

In this book, I'm excited to help you on this path to entrepreneurship by providing the essential steps to take, along with the tools and resources you can use along the way. If you are a woman reading this, you may already know that some of the challenges you face differ from those that your male peers may encounter, and in this book, you'll find specific resources designed to support you. If you are a man reading this, please keep going. I hope you'll not only benefit from the resources throughout the book, but I think you'll gain a deeper understanding of the positive impact you can create for others.

Wherever you are on your journey—whether you're simply thinking about starting up, or relatively far along—you'll find something to help and will be prepared to change the rules for yourself and others, one entrepreneur at a time. Moreover, I am confident that we can move beyond topics like “having it all” or “figuring out balance” and instead talk about the things a person can do to take control of her life. Lean In ends by asking all of us to continue the conversation on women, work, and the will to lead. My hope with this book is that we do more than keep talking. I am confident that we can tackle the bigger issues that women and men face as they work to build meaningful lives and careers. There are plenty of stories on why being an entrepreneur is hard, and I know many people may be daunted by the idea of taking that path. But there are also many stories that are seldom told of incredibly successful female entrepreneurs that you'll learn more about in this book as well. That's why I'm excited to share what's possible and help you on your journey to building a business and the life you want. Are you ready to get started? I know you can do this…

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How to Read This Book

The book is divided into three sections, each containing multiple chapters, developed to help you build your business: I. Get Ready to Start Up II. Building for Scale and Avoiding the Traps III. Lead and Operationalize. Section I is designed to help articulate the reasons to consider entrepreneurship and the initial steps you'll need to take to get started. Section II is designed to help entrepreneurs as they work to develop their initial business plans and consider funding. Section III is designed to help entrepreneurs who have successfully built a business consider how to effectively lead and operationalize. In each chapter, you'll find a brief narrative that helps to outline the challenges entrepreneurs, and, in particular, women, often face, by leveraging fictional characters, a real-world example from my experiences or other well-documented scenarios, and practical resources that range from tools to create business plans to guided meditation. I've organized the book in a simple, formulaic way so you can read cover to cover, or skip to the chapters that are of most interest to you. As I set out to write this book, the individual challenges that women encounter along their professional and personal journeys felt too big to take on by simply sharing my own story. That's why each chapter starts with a brief narrative of fictional characters, designed to explore the various challenges that women face as they navigate their careers and consider entrepreneurship. To help you keep track of who's who, here's a list of the cast of characters.

• Jill Saunderson: An experienced executive. Currently serving as a senior executive for a large company, she also serves on several advisory boards. A leader in her tight-knit community, she also actively mentors other women.
• Maria Paola: An entrepreneur and software developer. She's building her startup company by night and coding by day at her day job.
• Sophie Anderson: A former director of marketing for a large company who is now a stay-at-home parent.
• Jake Anderson: Sophie's husband, who is a mid-level manager for a financial services firm.
• Carolyn Robinson: A mom and friend of Sophie's.
• Hannah Smith: A project manager for a mid-size software company, struggling to find a path to promotion and advancement.
• Stan Brown: A project manager for the same mid-size software company that Hannah works for. He's a confident and trusted peer mentor to Hannah in many ways.
• Allen Monroe: Hannah and Stan's direct manager. He's a senior leader in the company. Through the fictional narrative, you'll gain a deeper understanding of the challenges many of the statistics and studies highlight. The second portion of each chapter is designed to pragmatically break down the challenge described and provide practical resources to solve them.

These tools, which range from drafting your first business plan to guided meditation techniques, will empower you to build the business and life you want. So, let's get started! You can do this!