The Lift Out

I’d just turned 29 when I learned what a “lift out” was.

I was a senior strategist at an ad agency, and I was flying out to Colorado with our agency chairman to help position our first lift out: the top two guys at a major financial firm were planning to leave their parent company and start their own place. They were taking their staff and book of business – a big book of business – with them. Their new firm needed a brand. And after several weeks of conversations they decided we were the agency they wanted to partner with. I knew at the time that my chairman was bringing me out there as a gesture – I’d worked hard that past year, had done well on some smaller projects. This would be a deliberately-over-my-head treat – go out, listen, see what I could learn. Apply it all someday down the line when I was the boss, the grownup in the room. The whole thing was an air-tight secret. We couldn’t email about it. We didn’t open a job number. My chairman didn’t tell his wife where he was going or why. I felt like David Ogilvy meets James Bond. I. Was. Pumped.

Paul and James* (you guessed it – not their actual names) were the #1 and #2 advisors in the world at their company. James was everything you imagine when you think about a top financial guy – charming. Hilarious. Instantly familiar and ingratiating. Smart and effortlessly cool, that prep school aura still lingering decades after he traded a crested blazer for a tailored suit with no tie. The majority of the team was just like him, but a shade less impressive – some a bit younger, less well spoken. A couple you could tell came from townie stock but looked the part with expensive haircuts and ArcTeryx vests. They had wide smiles and identically firm handshakes. They all threw their heads back when they laughed.

Paul was the #1. He was quiet. Ex-military. He held his hands folded on top of the table. He rowed every morning on the lake by his home on the west coast, whenever he wasn’t traveling the country meeting with clients. He made the investment decisions. All the vocabulary I studied on the plane to sound smart when we met them – portfolio strategy, ETFs, buy-and-hold, commodity futures – that was Paul. The relationships that brought ultra-high-net-worth clients into the firm were his team’s. The performance that kept them there was his. He reminded me of my grandfather. Someone who radiated principle and stoicism and self confidence that never strayed into hubris. Someone I desperately wanted to impress from the moment I met him. Someone who looked commandingly large from across the room – always shocking me when, standing shoulder to shoulder with him, it turned out he wasn’t much taller than I was.

Paul hosted the three-day brand planning session at his house in Colorado, a spectacular four-story chalet at the base of a mountain in a gorgeous resort town. I sat beside my chairman at the 18-person dining table, a wall of windows in front of us looking out at the mountain peaks that were stippled with snow even though it was almost spring. The guys – they were all guys – answered my chairman’s positioning questions with a swagger and excitement I hadn’t heard matched in any client meeting before. What made them different, why they were uniquely poised to succeed, where they saw the company in 5, 10, 15 years and what it would take to get there. I took furious notes. I phonetically spelled out financial terms I’d never heard of before, starring each as a mini-assignment to look up that night when the session was over. I felt like a secretary, not a strategist. I was painfully aware that I was the girl in the room who wasn’t talking. It was only after the session ended and I was back in my hotel room Googling that I realized Paul hadn’t spoken much that day either.

Paul hosted dinner for all of us on the second night. I remember James and all of the guys coming up to me at various points throughout the evening and making pleasant small talk. I don’t remember about what. I remember feeling a mix of gratitude and embarrassment that they made the effort. I sipped a single glass of wine and made sure to enunciate. I remember feeling like I should be at the kids table.

Paul brought me my coat after dinner as my chairman and I were leaving. “I hear you’re a rower,” he said. “I have an erg here at the house – I’ll put it out on the deck if you want to come by and do a workout in the morning. I’m up early and I’ll leave the front door unlocked.”

I got up at 4:50 without an alarm. Trudged over in the pre-dawn cold, a nervous pit in my stomach, eager to see him – and for him to see me. I’m young and new at this, but I know how to grind and I work my ass off and that’s something you and I share – see? I took the elevator up, opened the unlocked front door, and saw the erg waiting out on the porch on the other side of the glass. Just like he promised. I walked gingerly through the living room and had my hand on the porch door latch when I realized the entryway to Paul’s office was directly to my right. He was already at his desk. Three screens shielding his face. Shelves of books and binders behind him. The soft click of his mouse just barely audible in the morning silence. Doing the work. And for the first time I could see it: this lift out – this brand new company about to be born, likely about to kill its mother – wasn’t James’s. It wasn’t the team’s. It wasn’t “theirs.” It was his. His decisions. His ups and downs charted on the graphs and catalogued in the spreadsheets. His accolades when things were good. His phone ringing before 5 a.m. when they weren’t. “Morning,” he said, “enjoy it.”

I thanked him quickly, ducked outside, sat on the erg and started pulling. I listened to the whir of the fly wheel as the machine warmed up. I imagined Paul’s eyes on me instead of on his screen. I didn’t take any breaks – what if he was watching? And if he was working, so was I. Twenty minutes became forty. Forty became an hour. A little after 6:15 I heard the glass door open behind me.

Paul walked out onto the deck carrying two mugs of coffee and handed one to me. “I’m cutting you off. You’re at altitude and you’ll make yourself sick.” He pulled a lounge chair over, positioning it a few feet from where I sat on the machine, and lowered himself down. My heart was pounding. What could I say to him? Something funny – smart – maybe I could incorporate a couple of the terms I’d learned the night before.

“Don’t be freaked out if your splits aren’t where you want them. It always takes me at least two weeks of being out here before I start seeing the numbers I want,” he said.

I laughed and the sound of it echoed. “Thanks. There’s nothing I like better than an excuse,” I said. What? As soon as it came out of my mouth I wished I could suck it back in. That’s what you decide to say to the #1 guy who rows and starts companies and kicks ass at everything he does? Christ. You do belong at the kid’s table.   

He smiled – kindly, it seemed – and I turned away to stare out at the mountain before he could see me flush bright red. The sun was beginning to rise, not visible yet. Just a soft pink glow starting to spread, coloring the rippling undulations of the hillside, calm like a bay at low tide.

“I haven’t spent much time here since last fall,” he said. “My wife and I were out just after the kids went back to school. It was our last night and I was sitting right in this spot and I hear ‘Paul! Paul! Get down here and do a run with us.’ It was a client, a long-time client. I waved to him and said, ‘No, no, we’re about to get ready for dinner.’ ‘Paul! Get your ass down here!’ He wouldn’t let up. I thought, God, I don’t want to do this. But I got my gear and I met him at the chairlift and we went up. When I got to the top I didn’t like it. The sun was already low. Too low. In that kind of light the mountain starts to look flat. You can’t see the drop offs. But I was up there and I had to get down somehow and I’ve been skiing this mountain for twenty years. So off we went. We weren’t more than two hundred feet from the bottom when I caught my edge and felt my ankle pop. I couldn’t believe it.” He paused. I turned to look at him. He was smiling ruefully. And then he wasn’t. “But then I thought – of course you can. Of course you can believe it.”

He took a sip of his coffee. The steam of his breath caught the shimmer of the daylight that was finally cresting the ridge. I felt small. More than I had in the work sessions. More than I had at the dinner. I felt suddenly embarrassed that I hadn’t broken more of a sweat during my workout. I felt a little bit in love with him. I didn’t want the last morning of this last day to make it to the top of the mountain.

“Way to get it done,” he said, turning to me. He clinked my coffee mug with his and went inside, sliding the door closed behind him. I knew he was walking back towards his desk but all I could see was my own silhouetted reflection in the sun, now risen, reflecting off the glass.

We had a final session that morning before getting on the plane back home. My chairman facilitated, the team talked animatedly, Paul listened quietly and intently. I didn’t take notes. On the flight my boss chatted in low tones but excitedly about the possibilities – naming options, visual identity, go to market strategy, where we’d start.

Someone from the team called two weeks later. Paul’s book was down for only the second time in eighteen years. It wouldn’t take long to correct but right now their clients would be skittish about leaving and the markets were sluggish and the timing just wasn’t right. They’d call us when they were ready to talk next steps.

I still check their LinkedIn profiles every once in a while. They never left.

This year I’m turning 38. And for a couple of months, or maybe more, I’m going to lift out. Out of the company and city and community that have been my home for years. Decades, really. And as I’ve thought about what I’m doing – without any kind of concrete plan, or any clear idea of what I’m running from or heading towards – I’ve thought a lot about Paul. What stopped him from leaving? From taking that massive enterprise he’d built with his smarts and his foresight and his principles, freeing it from the bureaucratic trappings he found so irritating and stupid, and claiming it as his own? Growing it on his own terms? Feeling like it was truly his? The probable answer is the one that scares me most: his smarts and his foresight and his principles.

I’d like to think I have those things. I’d like to think they’re foundational to who I am. But the past year has made me question everything and left me unsteady in my skin. Why did I agree to be hidden away in a relationship with a man I fell in love with, waiting for word of when I had permission to exist in his complicated life and when I had to disappear again? What was missing in my life – what kind of tiny voids had started to crack open in my career and my sport and my existence in this city, little black holes of imploded meaning that this one man expanded to fill? Why did I – why could I – channel so much energy and time and emotion away from my own life and into his, and get away with it?

Sometimes when I look outside my much more modest window, particularly at sunrise, I think I can see something like what Paul saw. Spring not far off. The days getting longer. A river returned to its liquid state, rowing back on the daily agenda, leaving the office before nightfall, time spent with friends in the open air again. A way for everything to stay the same, and somehow feel better. A way for all the comforts of the known, situated in a shifted context of more daylight than shadow, to feel like enough again.

But I know, no matter how beautiful and safe and calming that view feels, it’s just a trick of the light. Something is off. Something’s missing. Something made me restless and anxious and full of enough self-doubt to deprioritize my wants and needs and ambitions for the first time in my life, for more than a year. I don’t know what it was. But I know I haven’t fixed it.

Right now, the truth is there’s nothing I’d like better than an excuse. An excuse to stay put in the safety of the routine I’ve kept, by and large, for fifteen years. But instead I’m going to channel my inner grown up. And I’m going to take a chance. I’m going to do the work I love in a new city, on my own schedule, in whatever wifi-enabled spaces I wander into. I’m going to get back to some hobbies and interests I’ve let languish, and try a couple new ones on for size. I’m going to let myself be lonely for a while. Because I think I need to make that an okay thing to feel again. And in this new context, loneliness might feel downright normal. I’m going to take the things I am, and that I’ve built, and that I’m capable of, and I’m going to put them out into the universe to see what happens. I’m going to trust my smarts to keep me afloat. My principles to keep me honest. And in the absence of any kind of real foresight – well, it’s 2020. And that’s got to count for something.