Seven Years Ago, California
Back then, I would have told you there was no better place in the world than California. The dry heat, the sunshine. The mountains and beaches. And the golden SoCal haze that everyone seemed to be drafting off of. It was perfect, and I knew I was exactly where I was supposed to be.
Even on the days James from marketing barged into my office without knocking, grinning like he’d solved world hunger, waving a one-sheet I already knew was going to be a very bad idea.
I was halfway out of my heels, leaning against my desk, finally letting the ache in my toes catch up to me. Late last night, Simon had called from Park City to say his pilot had grounded their return flight due to weather, leaving me to meet the Silverbridge Group this morning to give his pitch. I’d given the presentation on only three hours of sleep. I nailed it, too—clean, quick, persuasive. The investors were happy. Simon would be happy. And I was finally catching my breath.
“You’re going to love this,” James said, and I preemptively added it to the long list of things James was wrong about.
James wasn’t known for his hard work or ability to appreciate nuance. He liked big gestures and louder voices. He liked to restate someone else’s contribution in a meeting, explaining he was “putting a finer point on things.” He also liked to tell stories that were three times as long as they needed to be. Every ounce of him exuded entitlement, so I shouldn’t have been surprisedthe first time he tried to take credit for a strategy deck I built in my early months on the job. When I called him out, he told me to “take a breath,” suggesting with my level of experience I was lucky to be in the room at all, and then said it was all a part of “how things get done.” Like theCircle of Lifefor corporate grifters. I’ve disliked him ever since. People mistook his ability to filibuster a lunch for charm. But I couldn’t pretend I was so easily fooled.
Being chief of staff to Simon Avery, Redwood Security’s CEO, was an endurance sport—the kind that kept me buzzing on a sort of runner’s high. Twelve-hour days in stuffy boardrooms and a phone that never stopped pinging at me were the norm.
As James waved the one-sheet in the air, my Slack messages were chiming somewhere behind me.
“A friend of mine is a producer over at CBS, and they want Simon to do an interview. Four minutes on theirSunday Morningshow.” James put the paper on my desk with a triumphant smile.
I understood why it sounded like a big get—my college-professor parents used to watch CBS’sSunday Morning.The symphonic theme song at the top of the show had been some kind of catnip for them.
“Tell your friend thanks but no thanks, James,” I said, folding the paper in half and handing it back to him.
Redwood was Simon’s baby—a sleek home security start-up he’d founded in his twenties that ballooned into a billion-dollar juggernaut. What Nest did for thermostats, Redwood did for front doors, back gates, and entire neighborhoods. After securing his place near the top of the tech hierarchy in Silicon Valley, Simon relocated his company to Silicon Beach in Los Angeles. He liked the glossier vibes here—the sun-soaked atmosphere and the proximity to those whose names showed up in the credits of award-winning films. He came by it honestly, having been born in Bel Air. He ran with the kinds of power brokers who never waited long for anything—not opportunities, favors, or a booth at the Polo Lounge.
I wasn’t one of them. But I wanted to be. I wanted the kindof power that comes from people knowing who you are before you walk into a room.
So I had been putting in the hours for years. People had thrown their cellphones at me, hit on me, and cried to me. I took it all in stride, and in return, Simon mentored me. I kept up with balance sheets and companies’ growth strategies the way some people pored over sports statistics or celebrity gossip. And if Simon made a passing mention of an article he’d read, I read it, too—book, blog, translated opinion piece from theHong Kong Economic Times.
The momentum was like oxygen to me. I lived for it.
But I didnotlive for James. In fact, the way he pouted as I turned down his pitch made me want to drop-kick my laptop into the Pacific.
I’m toeing a line in Jimmy Choos, James. I’m gonna need you to get on board.
“Este.” James chuckled. “I don’t think you understand. CBS is a big deal, andSunday Morninghas been on the air for nearly fifty years.”
This was a classic James negotiation tactic. It couldn’t be thathewas wrong. I must have misunderstood, being the doe-eyed young woman I was. Ordinarily, I would have braced myself for James to talk my ear off about the history of television itself—name-dropping whenever he could find the opportunity—until I could come up with a diplomatic way to shut him down. But I was tired. And my feet hurt.
“I know whatSunday Morningis, James. But there’s not a single reason Simon needs to appear on a morning show whose core demographic is retirees still trying to figure out how to turn off the ringers on their cellphones. They’re not his audience. Not his clients.” Part of my job was acting as a gatekeeper for Simon. Ideas like this had to come through me. Whether James liked it or not.
“It’s prestige,” James said, clearly missing the point. Because of course he was.
“Prestige doesn’t jump the S-curve,” I said. “The board doesn’t care if he does a morning show. They care aboutfunding, adoption, scale. And he can’t be focusing on that if he’s yucking it up on some show watched by zero percent of our target audience.”
“This isn’t really a talk show format, Este. It’s—”
“You’re missing the point, James,” I said. “I’m sorry. But it’s a no.”
James left my office in a huff, and I opened the window by my desk as I sat down to weed through my new messages.
It was dusk, and the air outside was warm and unhurried—atemporary respite from another high-velocity day. A touch of salt from the Pacific lingered in the breeze that swept through Venice that night, and I took a deep breath.
My love for California was the swoony kind. It was my chosen home, and now that I had found it, I was never leaving.
I didn’t always live in California, though. I grew up in Boston, spending my childhood years watching red and yellow leaves fall on the ground and boats thread their way under the bridges of the Charles River. I was always cold, always in tights and plaid, and everything looked like it was from L.L.Bean.
My parents loved it there. They were realist types who saw the experience of raising a child like they saw everything else: as an academic problem to be researched, reasoned, and organized. There was no Santa, no TV, just flash cards and full transparency; they were convinced knowledge alone would shape me in their image.
And for a while, I bought into their pedagogy.
