Prologue

Happiness Is an Accomplishment

How I came to be a student of personal growth, positive thinking, resilience, and happiness is a bit of a horror show, honestly. Two failed marriages and family turmoil forced me to navigate through some serious shit.

My early life went much better. I grew up in an idyllic Idaho lake town with a solid, loving family, surrounded by a large group of close friends and constant adventure—a storybook come to life. I took it for granted and assumed that most people had this foundation.

I went to college at Gonzaga University in Spokane, Washington, with a plan to become a high school football coach. Both of my older sisters were in school there, and I had cousins, aunts, and uncles who were Zag alumni, too. It was a family thing and, if I learned nothing else from my parents, I learned to cherish family at an early age.

My introduction to journalism came during my sophomore year. I had a weekly assignment to write a news article that would be passed on to the college newspaper editors for review, and they published the first article I submitted. Once I saw my byline in the school paper, I was hooked. After graduation I started working as a sportswriter for local newspapers, combining my passion for sports and journalism. Writing came easily, and watching sports while getting paid (very little) felt like a no-brainer.

A couple years later, I was bored. Covering sports felt like the movie Groundhog Day. Everything had a set schedule, a defined cadence. Football followed baseball, basketball followed football, and so on. One summer night, sitting by the campfire at my family’s lake cabin with my first wife, we thought up a new plan: quit our jobs and move across the country so I could attend graduate school and get a master’s degree. Part of me still wanted to coach, and I thought teaching in college seemed like a sensible alternative and a fulfilling professional future.

After completing my master’s degree at the University of North Carolina in Chapel Hill, we moved back to the Pacific Northwest. I started working for newspapers again, this time on the digital side and in management. Eventually I started writing books about digital journalism at the suggestion of a respected colleague.

At the time, new technologies and new internet platforms exploded into our lives. I developed an insatiable entrepreneurial itch as I tried to help newspapers transition into this digital age. Eventually I quit my job to launch a startup company in 2008, right into the teeth of the global recession. Despite the timing, it seemed like we had a safe plan to manage our family finances, which included budgeting to send our two young children to Catholic school. My wife had a full-time job and benefits, our safety net. But the following year, she got laid off. We had to meet with the principal of the kids’ school to ask for financial help. My startup company struggled as the customer base reeled from the recession. I managed to earn enough money with speaking gigs and consulting work, thanks to my books. This work meant that I traveled often. Still, my wife and I were both consumed by the stress of not knowing how we would pay the mortgage in a few months.

Then, things went totally off the rails. I discovered my wife was having an affair. My work travel, while keeping us financially afloat, was taking me away from the marriage when she needed me home. She had also stopped paying the mortgage and other bills, while running up massive credit card debt—and I had no idea any of this was happening. We went through three different marriage counselors, and I started seeing my own therapist. We tried everything we could to save the marriage, but nothing worked. I had never been to any counseling and grew up associating therapy with weakness, thanks to the culture around me. Over time, I began to see the benefits of therapy and counseling.

I spent the next few years sorting through my own guilt, anger, depression, and anxiety over the impact this would have on our kids. The shame of failing at the one thing I knew I wanted to do with my life—build the kind of family I grew up in—haunted me. The requirements of a job can’t be separated from the demands of a family, and I failed to balance the two. They are at odds but totally dependent on each other.

It took more counseling (and lots of books) plus countless, deep, soul-searching conversations with close friends and my sister to sort through the guilt, anger, depression, and anxiety. My mantra during this time, “just keep doing the right thing,” helped me focus on being the best dad I could be. I didn’t want my kids to feel like they were growing up in a “broken family.”

A few years later, I started dating a woman whom I had known professionally for a couple years. She lit up my world in a way I didn’t know was possible. I had never been so close to someone as dynamic, inspiring, loving, and fun. Everything in our relationship happened fast. We were engaged in six months and married within a year. I knew she battled anxiety and depression, but I was confident I could “save” her. She worked harder at managing life than anyone I’d ever met. She had no choice. She had to work ten times harder than most people do just to be a normally operating person in the world. I learned so much from her about how to be a better person—and a better partner—but it turned out to not be enough.

When I asked her to marry me under the Bean, a sculpture in Chicago’s Millennium Park, it felt like I was living in a movie. We frequently shared the deepest talks of my life and, when the energy between us flowed in the right direction, I struggled for words to describe the feeling. I told friends it must be like winning the Super Bowl as a football player: realizing your dreams coming true right in front of you.

But our dream-come-true became a nightmare. Once we moved in together everything quickly fell apart. Her anxiety and depression got worse and worse. The rollercoaster ride that once had ups and downs became a constant downward spiral into chaos, hurt, anguish, and fear. She became physically abusive; I routinely had scratches and bruises on my body. I locked myself in the bathroom a few times to escape. The police intervened—twice. She was suicidal. Once I tackled her in our bedroom to wrestle a knife out of her hands as she threatened to use it on herself.

We tried counseling—hours and hours of counseling. I read more books, and had more soul-searching conversations with friends and family. I learned everything I could about abusive and dysfunctional relationships—how to fix them and, eventually, how to end them.

I was deeply concerned about my kids and the toll this marriage was taking on them—and on our relationship. I had shared custody fifty-fifty with their mom since our divorce, but eventually the kids asked to stay at their mom’s house full time. I couldn’t bear the thought of losing my kids. On a sunny spring day, confident that I had done everything in my power to make it work, I walked away from my second marriage.

As my kids and I adjusted to our new, more peaceful life, my younger child confided in me (and his mom and brother) that he thought he was born the wrong gender. He wanted to start exploring a female-to-male gender transition. (He attended a Catholic school where the uniform required girls to wear a plaid jumper, only one of many new challenges we had to navigate.) I had never met a transgender person, and had no idea what it meant to have gender dysphoria or what a transition entailed.

Enter: more counseling, more books, more deep soul-searching conversations with friends and family.

And this time I had a new job to get the hang of, too.

I had just accepted a job as a consultant with a firm out of Los Angeles. Before that, I had been working at a TV station in Seattle for seven years, enduring a brutal commute from my house in Tacoma. I had spent almost three hours each day driving, catching the train and walking to the office. In my new role, I worked from home but traveled frequently. I quickly discovered I loved working from home and traveling every couple of weeks to visit places like New York, San Francisco, Chicago, and Los Angeles. The relief from the daily commute and the excitement of a new opportunity couldn’t have come at a better time.

***

My job gives me the chance to work with people at all levels, from the bosses and corporate presidents to the front-line staff. The challenges we are facing together—leading companies through massive disruption and trying to stay relevant to ever-changing audiences—has given me the perfect lab to test ideas on what a modern, adaptive culture should be. There’s no road map, though. I’m inventing my job on the fly every day.

Luckily, I have plenty of support, from books and through conversations with smart, innovative friends and colleagues—and anyone else who will help me.

I also went back to school. As I had set out to do all those years ago, I began teaching in college. As luck...