Reboot

Leadership and the Art of Growing Up

Jerry Colonna

• Publisher: Harper Business
• Year: 2019
• Print ISBN: 9780062749536
• eBook ISBN: 9780062749505
• Topic: Economics
• Subtopic: Business Development
• Index: Economics

One of the start-up world’s most in-demand executive coaches—hailed as the “CEO Whisperer” (Gimlet Media)—reveals why radical self-inquiry is critical to professional success and healthy relationships in all realms of life.

Jerry Colonna helps start-up CEOs make peace with their demons, the psychological habits and behavioral patterns that have helped them to succeed—molding them into highly accomplished individuals—yet have been detrimental to their relationships and ultimate well-being. Now, this venture capitalist turned executive coach shares his unusual yet highly effective blend of Buddhism, Jungian therapy, and entrepreneurial straight talk to help leaders overcome their own psychological traumas. Reboot is a journey of radical self-inquiry, helping you to reset your life by sorting through the emotional baggage that is holding you back professionally, and even more important, in your relationships.

Jerry has taught CEOs and their top teams to realize their potential by using the raw material of their lives to find meaning, to build healthy interpersonal bonds, and to become more compassionate and bold leaders. In Reboot, he inspires everyone to hold themselves responsible for their choices and for the possibility of truly achieving their dreams.

Work does not have to destroy us. Work can be the way in which we achieve our fullest self, Jerry firmly believes. What we need, sometimes, is a chance to reset our goals and to reconnect with our deepest selves and with each other. Reboot moves and empowers us to begin this journey.

Chapter 1
Passing GO

Mom was my Monopoly buddy.

When I was a boy, Mom and I spent hours playing Monopoly. To this day, I love rainy days, in part, because back then, when it rained, we’d spend the day playing board games, from Chutes and Ladders to The Game of Life. But I loved Monopoly most of all.

I loved that it could take hours to play properly (not the “shortened” version, where you dealt out the cards representing properties, but the right way . . . the way according to the rules . . . where you collected properties only after landing on them and buying or trading them). I loved collecting those deeds. I loved being the thimble, the iron, the dog.

I loved passing “Go” and collecting $200. I felt great about amassing money but, most of all, I loved surprising people with what I was capable of doing.

When I was a boy, I wasn’t often seen. I was looked after, cared for. I was held and comforted, especially after some painful experience. But I wasn’t often seen. I was a good boy when inside I wanted to rage. I tried hard, all the time, when inside I wanted not to care. I was compliant, and therefore complicit, in not being fully appreciated.

When I was a boy, and we played Monopoly, everyone would lay out money in front. Piles of currency neatly stacked and sorted: $500s, $100s, $50s, and so on. Not me, though. I’d keep all my money stacked together, under the game board. I didn’t need to lay it out in front of me to know my worth. I’d keep track in my head of how much I had. And I’d surprise everyone by buying up their properties when they were bankrupt. I’d surprise them with my cleverness and cunning.

When my cunning, my skills, my ability to understand and work with money would be revealed, I’d feel seen not for being good—quiet, compliant, a “good boy”—but for being me—a good person who was also smart and skillful.

What’s more, at seven, I came to understand that, while people might not see you, might not get you, you could use that fact to survive.

The Game of Life, Hi! Ho! Cherry-O, and Monopoly taught me about life.

I learned, for example, that you needed money to win, to be safe, to never be hungry. With it, you could buy real estate, you could put little green houses on those properties, and then, over time, generate more money. If you played the game right, you could generate enough to make sure that Mom and Dad didn’t fight about having enough food. Dad wouldn’t yell at Mom if you took more than two Oreos.

There were nine of us in the two-bedroom apartment on the ground floor of a small Brooklyn building owned by my grandfather. I was born in December 1963, a month after JFK was killed. By then, my oldest siblings, Vito and Mary, were already beginning to cycle in and out of the house. While the same small space was home for all of us, it was rare that we’d all be there at the same time.

Dad was a foreman at a printing company, a place at which he had worked since high school (and to which he came back after serving in the army). Mom stayed home with us.

Dad was a good man whose broken heart sometimes led him to drink to drunkenness. Mom was a good woman whose broken childhood led to mental illness that further led her to hear and see things that, as often as not, weren’t there.

Together, they had more kids than they could afford, financially as well as emotionally. Being number six of seven, I grew up wondering whether it was I who had tipped the scales, broken the camel’s back. I worried I was the mouth that was one too many to feed; the one who caused the whole lot of us to never have enough to feel safe, warm, and happy.

My mother’s father, Dominic Guido, was an iceman. He sold ice in the summer, coal in the winter, and homemade wine all year long. Mom always said his shoulders were covered with hair to protect his body from the fifty-pound blocks of ice he carried up the stoops of houses in Brooklyn. He’d dropped out of school in the sixth grade, in his home village in Italy, Palo del Colle, just outside Bari. He’d made his way to the States and become an entrepreneur—someone no venture capitalist would ever fund, even though he understood the most important principle of business: end the day with more money than you began it.

Grandpa always seemed to have enough and even a little extra to spare for us. He owned the building where my family lived, the same building where my mother and then later my sisters would mop the hallways. Grandpa would visit on Saturdays, usually bringing food. My father would stiffen as Grandpa came down the hallway and into our apartment, filling the room with the smell of woolen underwear and Old Spice.

Grandpa and Dad had a hard relationship. There were a few possible reasons.

From Grandpa’s perspective, I could see how he might have blamed Dad for their having had all of us. Mom was pregnant with my brother Vito, after all, when they got married. “She had too many kids,” I imagine him thinking, “that’s why she was sick.” And, of course, to their Catholic eyes, it was a sin that Mom was pregnant before marriage: “She sinned, that’s why she got sick.” Devoutly religious, Mom must have been racked by guilt. I can hear her assuaging her guilt now: “I would have had a dozen,” she’d say all the time, speaking of us kids, “if only the doctors would have let me.”

Maybe, from Grandpa’s point of view, it was Dad’s beers. She would yell all the time about his drinking (which worsened after his time in the army), right after they were married.

In manic moments, Mom would slam the table and focus on Dad’s two six-packs of Pabst Blue Ribbon a night. When she was kind, she’d guess that the stench of the Nazi death camps he’d visited in postwar Germany caused him to drink. When she was unkind, she poked at the fact that he wasn’t really Italian, that he’d been adopted by an Italian family and he was really a drunk German or Irishman.

“If only he weren’t a drunk,” I can hear Grandpa saying to himself, “then my daughter wouldn’t be sick.”

But maybe the tension between Grandpa and Dad was rooted in the family splits that went all the way back to the pale limestone of Palo del Colle outside of Bari. In that tiny village, both Dad’s mother, Mary Colonna, and Mom’s mother, Nicoletta Guido, were cousins. But not just cousins; they were rivals. As a girl, Mary was orphaned and raised by her aunt. Nicoletta and Mary were, in a sense, sisters.

To heighten the tensions, each of them married an iceman; Mary married Vito who was never the entrepreneur that Dominic was.

If I were forced to guess, I think Grandpa blamed Dad for Mom’s illness. Her delusions, her mania, her depression started around the time they got married. “If only she’d married someone else, had had a different life, was able to go to art school as she’d hoped,” I imagine him saying, “then maybe my baby girl wouldn’t be sick.” As a father now, my heart aches when I think of him worrying about his baby girl, my mother.

I weep when I think of Grandpa, helpless and angry, watching his baby, his seventh of seven children, being strapped into a straitjacket and carted away to a hospital to have her memories and suffering mind jolted with electroshock therapy again and again. And again.

It’s hard, even, to imagine his feelings as his daughter’s seven children were divvied up among her siblings and how he and my grandmother would take in my brother John and me.

Even when Mom wasn’t in the hospital, John and I would visit Grandpa and Grandma on Wednesdays after school. Their house smelled wonderful: of lemon drops kept in a tin in the hallway cupboard with the pale green door; of coffee ground with a hand-cranked grinder that hung on a kitchen wall beneath a photo of the saint, Padre Pio; and, in summer, of newly cut roses from Grandma’s garden and figs picked from the tree growing next to the porch at the back of their kitchen—a tree brought as a sapling from Palo del Colle and protected from winter by being wrapped in blankets and old rugs, with a bucket on top to keep the rain and snow out.

Such smells still drop me to my knees. I pass a tree whose springtime blossoms are just bursting out and am teleported, instantly, to Brooklyn’s Prospect Park on a cool April morning. The oddly tangy metallic smell of Coppertone sunscreen still makes me feel as if I’ve got grains of beach sand stuck in my teeth . . . remnants of the bologna sandwiches Mom would make for our trips to Coney Island. Smells bypass the cognitive, adult parts of my brain and go directly to my soul.

The smells of coffee, roses, and lemon drops signal I’m safe.

I grind whole beans and once again I’m five years old, snuggled into Grandma’s lap, my head on her bosom, rocking in her arms, safe, warm, and happy. Grandma and Grandpa’s house was my sanctuary from the chaos of home.

To my child’s heart, money meant roses, fresh figs, ground coffee, and lemon drops, forever. Money was safety. The pursuit of money, then, became a chase for safety and a flight from poverty, chaos, and the streets of my childhood.

“What will it take?” Dr. Sayres, my psychoanalyst asks me nearly forty years later. “When will you stop?”

I was in my thirties—a father, a success—and I would lie on her couch, staring at the ceiling. I’d been staring at that damn ceiling for seven or eight years already.

“Bill Gates,” I sputter, shocked at my own response. I never thought of myself as pursuing Gates-like wealth. I liked to think I was above that.

But as I lay there, I had to admit that, to the little boy who’d spent Sunday dinners hiding out under the dining room table, becoming Bill Gates–rich would mean lemon drops forever.

Money, of course, brought with it admiration. People thought I was smart because I had money. Some of these same folks had dismissed me when it seemed that all I’d amount to would be poet or college professor—wise but poor. Money, success in business, had given me access to power. Suddenly, it seemed, my opinion mattered to businesspeople, to politicians, to leaders of all sorts. To the people who, as a boy, I barely knew existed when I played scully, shooting bottlecaps filled with crayon wax on boards carved into the asphalt of East 26th Street in Flatbush, Brooklyn.

Money and success meant admiration, acknowledgment, accolades. M...

Table of contents

• Dedication
• Contents
• Foreword
• Dedication of the Merit
• Introduction: Elevating Darkness
• Chapter 1: Passing GO
• Chapter 2: The Crucible and the Warrior
• Chapter 3: Standing Still in Empty Time
• Chapter 4: Remembering Who You Are
• Chapter 5: The Immense Sky of the Irrational Other
• Chapter 6: Handprints on the Canyon Wall
• Chapter 7: Loving the Crow
• Chapter 8: Heartbreak, Resilience, and the Path to Equanimity
• Chapter 9: Leadership and the Art of Growing Up
• Afterword: A Light Heart Lives Long
• Author’s Note
• Acknowledgments
• About the Author
• Endorsements
• Copyright
• About the Publisher