INTRODUCTION

OVER THE PAST TWO DECADES I’ve pretty much become “the founder guy” in academia and beyond. I’ve immersed myself in studying the people who begin startups. My course and case studies, my database of twenty thousand entrepreneurs and interviews with hundreds of them, and my book on founders’ dilemmas were aimed at teaching people how to build successful startups and founding teams.

My focus suddenly expanded on a warm spring day in 2010. I was in my office on the campus of Harvard Business School when one of the students in my entrepreneurship course came into my office, full of excitement, to tell me that he would probably never start a business. With a startled laugh, I replied, “Sorry that you’re taking the wrong course, David!” “Not at all!” he said. “Your course has already changed my marriage!”

After letting that sink in, David explained that he and his wife had been struggling to communicate and make decisions about their next steps. He was nearing graduation, and questions around which of two jobs he should take had quickly evolved into “Who decides which city we live in?” and “Your career is taking priority over mine!” For David and many like him, relationship equality—both partners carrying essentially the same work and family responsibilities—is an assumed necessity. But as David had learned in class, the most effective founders resist the natural pull toward equality, instead giving each collaborator authority over a specific area. David had realized that splitting everything down the middle led to resentment, especially if both parties believed that all major decisions should leave both people equally happy. Now, with responsibilities clarified, communicating with his wife got easier.

Taking another lesson from the successful founders who make a point of having difficult conversations with their cofounders up front, David and his wife were tackling uncomfortable issues head-on and forcing themselves to anticipate challenges they might face. David had seen that rather than take risks as everyone assumes they do, founders identified and managed risks, and he and his wife were now doing the same. All of a sudden, they were more adeptly managing the venture that was their life together.

It was a lightning bolt moment for me. No one had ever extended my lessons to realms outside of founding, and none of the researchers I work with in entrepreneurship or my colleagues in personal change management had ever drawn the dotted line so directly between the two realms. David was right: Whether or not we will be founders, we can all learn profound life lessons from the counterintuitive practices and behaviors of successful entrepreneurs.

I also realized that I had been applying some of the founders’ lessons to my own life. Not at first, of course—when I was starting out as a computer engineer, I didn’t know much about startups. It wasn’t until I founded my own systems-integration practice and then worked with founders as a venture capitalist that I began to experience, observe, and analyze entrepreneurs’ best and worst practices. I turned observation and analysis into an academic career, first at Harvard Business School and now at the University of Southern California, where I recently started (yes, founded) a new academic center called Founder Central. As I pursued my academic interest—learning what leads to startup success or failure and developing courses on how to avoid the pitfalls—I discovered many ways to fit founders’ strategies into my career decisions, as well as aspects of my twenty-eight-year marriage and the parenting of my six daughters and two sons.

One of the benefits of being an educator is that the classroom allows us to experiment. So I started asking my students to pay closer attention to the deeper lessons in my case studies of entrepreneurs and in the experiential exercises I had developed to train my students to be better founders. For their semester-ending writing assignment, I had them “teach” one founding best practice to someone who could apply the best practice in a career decision, personal relationship, managerial challenge, or other “nonfounding” walk of life. I had lengthy discussions with students and alumni about the challenges they faced in these other areas. Many described how entrepreneurs’ exemplary tales had been useful as they came to points in their lives when they feared that their decision making was being skewed by their own blinders or their ability to shift gears was being thwarted by what we called “magnetic pulls” of similarity and equality.

The stories from the people I talked to reinforced my sense of the particular challenges of our age. Roles and expectations are increasingly up for grabs. Whether we freelance or work for large organizations, whether our family involves marriage and kids or something else, it feels as though we each have to find a new roadmap for our journeys.

In other words, life is a startup—and we are the founders of our own lives.

THE INFLECTION POINTS OF LIFE

This book is for people who may never have the name of a startup on their business card but want to be armed for life’s inflection points. It is a resource for those who might want to make a change or create a stronger foundation for a new endeavor, whether in their personal or professional lives. It may be particularly valuable for those in the early stages of their careers and in long-term relationships. But the book also offers important advice for anyone contemplating a new endeavor, whether it’s switching jobs, moving to a new location, or entering a creative activity. The challenges explored in this book can arise at almost any point in life and for a wide range of people. This includes those who are midstream in their current lives but who are struggling to balance the demands of work with the responsibilities of family while still trying to figure out how to pursue their most cherished dreams. In addition, if you are a founder, this book will help you readily apply to greater effect the hard-knocks lessons you may not know you know.

I draw on numerous sources that hold insights for many of the most important decisions that we face in life. We learn from the direct experiences of a wide range of individuals at different stages of life and career, from young people seeking greater meaning in their jobs to couples pursuing work-life balance to midcareer managers looking to climb out of the corporate rut. I also mine my rich database of nearly twenty thousand entrepreneurs and the insights from my firsthand work with founders like Tim Westergren of Pandora Radio, Evan Williams of Blogger and Twitter, and Hillary Mallow of ProLab. I tap my own founding experiences; my discussions with students, alumni, and others facing a wide range of life dilemmas; and my interviews with past, current, and aspiring entrepreneurs.

As a result, I’m able to go deeply into the entrepreneurial mind-set to investigate the challenges successful entrepreneurs have faced, the counterintuitive thinking that sets them apart, and the relevance of their actions for our life decisions. I don’t suggest that all entrepreneurs are paradigms or even that all of them provide valuable examples. Instead, I’ve gleaned lessons from the smartest moves that I’ve observed over the course of twenty years. I tap the wisdom of the best at their most effective.

As a professor, I also draw on best-in-class research from a variety of behavioral sciences—including psychology, economics, sociology, and family and gender studies—and the entrepreneurial wisdom in ancient writings, such as the Talmud and the classical work Ethics of the Fathers, to outfit you with lessons that are both rigorous and road tested. How have founders learned when to jump into new businesses and when to hold back? What are their secrets about sharing responsibilities, dealing with failure, and planning for success? I explore how their best practices can help each of us make better decisions, solve problems, manage relationships, and achieve growth in both our personal and professional lives.

ENVISIONING CHANGE AND MAKING IT HAPPEN

The book is divided into two parts. Collectively they cover the most important lessons my Founder’s Dilemmas course has to offer that are also applicable to nonfounding walks of life. In the first part, I talk about envisioning change. Because long before anything occurs, something is happening: problem framing is just as important—if not more—than problem solving! Then, I consider managing change: how we can best execute on the plans we envision. Each part includes chapter pairings that address problems and solutions in turn. The first of each duo focuses on the challenges that we face in life, drawing parallels between the personal-life challenge and an equivalent founding challenge. The second focuses on the solutions to those problems: I look at how founders tackle those hurdles and how we can apply their approaches ourselves.

Part I, on envisioning change, begins with a duo of chapters that delve into factors that prevent us from making a desired change and, on the flip side, lead us to make a change too hastily. Some people are constrained by handcuffs that they progressively create for themselves. Others get so excited about a change that they become blinded by passion and rush in too quickly. We look at how founders overcome their fear of leaping while keeping even their most ardent passions in check and see how we can apply their best practices ourselves.

The next duo of chapters addresses the challenges posed by failure and by success. Our fear of failure prevents us from making changes, and when failure occurs, we suffer greatly. On the flip side, we don’t appreciate the potential perils of success—how achieving our dreams can lead to its own set of problems. These challenges apply to everything from applying for a promotion to contemplating a relocation to planning a radical career move. I look at how founders increase the chances that they will be able to fail well and to anticipate and manage the perils of success.

In Part II, on managing change, I look at decision making and problem solving—the kinds of challenges that arise after you have envisioned the change you want to make and are moving into the “doing” phase. We learn from founders the critical importance of thinking ahead despite, and even because of, our temptation to respond reactively to new developments.

First, I examine the risks of relying too heavily on our blueprints, or the well-worn personal mental patterns that we use to make choices. I discuss how the best founders tune into the potential disconnects between their existing blueprints and the challenges they are about to face and how they act to reduce those disconnects before they get blindsided by them. For instance, a powerful part of our blueprints is the inclination for birds of a feather to flock together, also known as homophily. We are naturally drawn toward collaborators who are similar to us, often to our peril. The best founders have seen the problems caused by this tendency, including heightened tensions due to overlapping capabilities and gaping holes in their teams. Rather than depending on too-similar collaborators, the best founders relentlessly take stock of their own weaknesses and recruit people with skills and viewpoints that differ from their own, even if that makes the founders uncomfortable.

I then turn to two powerful, but problematic, magnetic pulls: the tendency to involve family and close friends in our endeavors, and the allure of equality. I demonstrate why we are playing with fire when we involve those who are near and dear to us and how the best entrepreneurs diagnose the areas with the highest potential for blowups, creating firewalls to prevent those blowups. I also discuss the problems caused by the powerful pull of equality, both within our teams as we strive for fairness and in egalitarian personal relationships in which we take pride. While effective entrepreneurs have a healthy respect for consensus, they know that an overreliance on building a unified view can prevent progress. In addition to dividing responsibilities and giving each person sole authority over a particular area, they resist the siren song of equality when it comes to splitting ownership among themselves. The reality is that few collaborators—whether cofounders or couples—truly contribute equally, and I show how pretending otherwise can be counterproductive or even destructive.

I conclude with an exploration of a trade-off that most of us face at one point or another: What do we give up when we fight to maintain control, whether in a job, a project, or a relationship? And what do we gain when we yield control? When does it make sense to give up control to get those gains? For insights, I draw on my research into the rich versus king trade-off facing founders: if founders want to get rich from their startups, they can’t expect to be the absolute monarch; if they intend to rule single-handedly, they can’t expect the startup to reach its full potential, financially and in its impact on the world.

As I cover these topics, I investigate several themes that cut across each and recur again and again: How do founders apply rational thinking to harness and focus their emotions, enabling them to balance head and heart? How do they manage conversations about difficult topics, often with people close to them and with whom they tend to avoid such conversations? And how do they avoid being seduced by short-term gains? Starting a business often requires daily, all-consuming battles for survival—making it all the more impressive to see successful entrepreneurs fight those urgent battles while keeping their eyes on the distant horizon.

Whether you’re facing major decisions, an imminent move, or difficulties in a close relationship, these lessons can be applied to the constants of risk, growth, decision making, and problem solving. They can help you make more-informed choices about whether and how to act. My hope is that the lessons of the most effective founders will carry you along through whatever personal venture you launch—and bring you an outcome you will celebrate.