Introduction

How do we stay relevant in this ever-changing landscape? How do we spot upcoming trends that might affect us before we are in the crosshairs of obsolescence and disruption? How do we brand ourselves outside of a corporate role to sustain a contribution on our own terms? How can we find a tribe of our own away from the corporate watercooler? How can we measure our progress without annual budgets and performance reviews?

We’re worried. We don’t have time. We don’t have bandwidth to answer all those calls and messages, not even the one from our doctor who will tell us to lay off the stress and long hours sitting at a desk or on a plane or in a conference room.

We like our work or are at least proud of what we’ve built—the skills and credibility. We have a lifestyle we enjoy. We are near the top of the mountain, if not at the summit. And yet, what have we sacrificed? Family? Health? Dreams of making a difference in the world? It seems like a pyrrhic victory, a string of carcasses strewn behind us that negate the true sense of achievement we were hoping to feel.

But people are talking about a hundred-year life. What could we do if we weren’t doing this job? Who would want to talk to us once that director or doctor or partner title wasn’t on our LinkedIn profile or business card?

Where would we start in planning for the future? We don’t want to look silly. We don’t want to seem ungrateful for all that we have and all that we’ve been given. But we’re also scared shitless that if we don’t do anything it will leave us vulnerable, our careers at the mercy of the company’s board or disruptions in industry over time.

In writing this book, I’m making a few assumptions. Like, you have enough financial or career capital to take some risks, even if it means skipping your regular cappuccino. I take for granted that making a meaningful contribution and intellectual stimulation is important; that it would feel great to know you could quit or keep your job, on your terms; that taking a sabbatical, a day, or a week off to get your mojo back—or move to paradise full-time for that matter—would be an improvement on the status quo. I am assuming it would give you a deep sense of purpose to know you were making more of a difference again.

If the idea of work and life on your terms brings a sigh of wistfulness, you’re not alone. You can wake up excited for the work ahead. The world needs you being creative, innovative, solving problems, building and investing in companies, connecting people, and mentoring the next generation.

You are not obsolete, but you may need to upgrade your operating system to future-proof your career and contributions to create more meaning, joy, and purpose in your life.

Let’s go.

Why I Wrote This Book

I’d known my best friend Charlotte’s husband for fifteen years. He wasn’t the social type. I was puzzled when the phone rang in my Hong Kong office and I heard George’s voice. He never called me.

Pressing the phone to my ear, I heard his familiar, steady voice. “Diana, I need to tell you about Charlotte.”

His voice wavered. “She…she killed herself last night.”

I went cold. Dumbstruck, I felt the blood drain from me.

“What? Why? How did it happen?” I asked, and again, “Why?”

I stared at the computer monitor, seeing nothing. Row after row of emails blurred into a gray, unimportant, and trivial mass. My hands went cold and seemed like they belonged to someone else as they grasped the phone. Panting and dizzy with confusion and heartbreak, I could feel my mind grasping for something to do to keep the world from spinning out of control, but suddenly everything about my neat little office at Financial Times seemed alien.

The door creaked open. “Diana, we have a conference call in fifteen. Everything all right?”

“Yes, I’m fine. Just need a moment.”

People speak about pivotal moments that serve as a wake-up call, an invitation to stop living on autopilot. Charlotte’s death made me realize the shortness of life and the futility of making do. When I looked around, I saw many other people feeling the same way. The senior people in the board director programs I had launched at Financial Times were looking out at the next twenty, thirty, or forty years of increasing longevity and wondering what their role would be as an elder in the business community. With the pace of change accelerating, technology rendering their knowledge obsolete, and a globally competitive landscape, few can rely on a nice pension and guaranteed well-paid corporate board position at retirement. At the top of their game they were peering over a cliff wondering what the stepping stone might be to a new life that allows them to re-balance and invest in the hobbies, relationships, and interests that were sacrificed to get to the top. The good news is that the life of narrow reliance on one specialty is a risk that can be lessened by investing in a wider realm of activities and a broader network of relationships.

Around the same time as Charlotte’s untimely death, TEDx was auditioning speakers for an event on the theme of “crossroads.” A friend encouraged me to try out, and I signed up for the audition. What did I have to say about crossroads? I wasn’t even sure, but this was an opportunity to practice storytelling, and that was part of becoming a better writer, which I aspired to be. I thought I’d probably fall flat on my face, but that was okay because I was putting myself out there, and I was trying.

I don’t know what I expected, but I told myself that if I could help just one person, it would all be worth it.

Unlike in past years, the decision was not up to the judges but to the several hundred people who they had invited for the TEDx open mic. Each table had a rating sheet for the speakers. As I approached the microphone on stage, I was terrified, but I started talking, and the more I talked, the more relaxed I became. I told them about my friend Charlotte and how we were going to start our own consulting company and take over the world. I told them about how we had both done pretty well for ourselves, but somewhere along the way, we had abandoned our dreams and settled for being the women other people expected us to be. I told them about losing Charlotte and how that had driven me to a crossroads in my own life. I could stay on the path of least resistance, or I could be brave and strive to build a life that made my heart sing.

After my talk, a woman approached me at the bar. “I really needed to hear that right now,” she said. We talked for a while, and I knew then that I had helped at least one person.

I was chosen to speak at the upcoming TEDx Stage Event.

I spent a long time writing my speech. It needed to be real and raw and authentic, but I worried that I might be committing career suicide. One of my friends who read the speech laughed and said that it looked like I was going to live out my midlife crisis onstage. Was it trivial and narcissistic? Was I crazy to share such a personal story? Would it be just passing gossip to people? I wrote more and practiced more and then went to rehearse my speech for the TEDx organizers. One, a computer science professor, said he could completely relate and asked me to make it more relatable to both women and men. A television anchor was fascinated and asked for more visceral detail. They actually wanted to listen and could see how it fit into their own lives. It was more than just my story. I had learned something important that other people needed to hear. I had something to share.

The TEDx was held at the Hong Kong Performing Arts Center. There were two thousand people in attendance. The masters of ceremony were Angie Lau, a charismatic Bloomberg TV anchor, and Jesko von den Steinen, an actor, choreographer, and filmmaker. They even had Cirque de Soleil dancers at intermission. I was way out of my league.

I spoke and was overwhelmed by the response. People came up to me afterward to share their stories. Not just people in their forties and fifties but young people who told me they had great but unfulfilling careers and they didn’t know what to do. I had tapped into a fear—and a void—that people across generations were experiencing.

What I expressed that had resonated with these people is our need to give ourselves permission to live life on our own terms. This means pursuing our work within the context of our lives instead of living our lives around the edges of our work. It also means learning how to navigate a workplace where the traditional metrics of success are giving way to priorities of well-being and wisdom, influenced by millennials interested in meaning and boomers prioritizing growth and continued engagement into later years. It is fundamentally about being ambitious to live the life we imagine, not the one we’ve been given.

Afterwards, people continued contacting me. They wanted to talk about what was going on in their lives. I wanted...