I think it was after my fourth sleepless night that I sought out Scott Willett, my neighbor. He is another entrepreneur, someone else who’d left the corporate world for his own—which meant he was someone who might, at last, understand me.
“It’s not going well,” I’d said by way of opening, back in March 2021, the two of us bunched round the campfire he built in his backyard.
“What’s the it that’s not going well?” Scott asked. He has a Ph.D. in organization management, which, among other things, gives him a therapist’s demeanor, all open-ended questions in nonjudgmental tones.
“All of it, maybe?” I’d said. Only that wasn’t quite expansive enough. It was the uncertainty of entrepreneurship, sure, and the fear which hadn’t left me since I’d been laid off from my media job in November 2020 and decided to go it alone as a writer and course creator. What if I bankrupt us? What if my kids see me as a failure? What if my wife leaves me? Any entrepreneur knows that as what-ifs compound, they grow more dire. Scott knew it, too. But what surprised me, I told him, were the frustrations of my success. The wins were modest. Or they were large but not replicable, like good friends introducing me to better business partners in need of a one-time solution. Nothing was ever good enough, for long enough. Nothing happened fast enough. That was the big thing. I liked—and on many days, loved—being my own boss, but I loathed the irregularity of my paychecks and the days, months, years it would take to build out my future. I didn’t know if I had the patience for that, which was another way to say I didn’t know if I had the balls for it.
I told Scott that I wanted his serenity. I wanted his self-assurance.
“Because certainly everything’s not just peachy in your life,” I said.
“No,” he said, gently. “Not always peachy.”
Five years ago, he left Prudential as a vice president and global head of organizational effectiveness. He started a consulting firm, Pennington Human Dynamics, Inc., with his friend and business partner, Najeeb Ahmad. By the time I came to him, his business was thriving—though he kept a lot of his success to himself, out of deference to my mood. He
