We were kings. We reveled in record profits. We blew out key performance indicators and were all the talk of the office. Every Friday, my fellow financial analysts and I went to the bar for happy hour, to beat our chests like warriors and celebrate our victories. We were all mistaken and misled.
My new boss, Daniel, was in his early-60s. He was our division president, with a round, friendly face and mannerisms that seemed of a down-to-earth, small-town kind of guy. It stood in contrast to the snooty coworkers I dealt with. He always greeted me with a pluck of southern twang, “Hey Seany boy. How ya doin?”
If you judged this initial impression and assumed he was some kind of rural simpleton, you’d be sorely mistaken. Dan was brilliant. I had the privilege of being his right hand man during our meetings, under the impression I’d help him field questions from executives. Yet he didn’t need my help. His steel-trap memory retained all the smallest details that board members drilled him over. He never stressed excessively or floundered under pressure. He was wise and kind to everyone in the office. I came to greatly admire Dan, both as a colleague and as a person. He was a role model I studied like a book.
In the summer of my second year of working for him, I got a strange request. Dan was out of office that day, and called me, “Hey Sean, I left my satellite phone in my desk. Can you bring it to me at my house?”
“Satellite phone? What does it look like?” I said. He directed me to a drawer, where there was a big phone that was shaped like a brick.
Dan was going on vacation to Russia for two weeks. It was a long overdue trip his wife wanted to take with their kids before they left for college. He was afraid of not having access to work calls and board member questions, so he insisted on bringing one.
A conversation I never forgot
I pulled into his long driveway and immediately noticed the spoils of his plunders. It was an 10,000 square foot house with an electronic gated entrance he’d given me the code to. I exited my car, surveying the surrounding homes with awe. Each one seemed more extravagant than the last. Before I got to the door, it slid open and his yellow lab came out, wagging his tail to greet me.
“Come in!” Dan said with a big smile. I stepped in to see a grand staircase, which spiraled elegantly toward a chandelier, which dripped with crystal. Art hung on every wall, the hallways feeling like a stroll through a museum. He had a two story library with a special sliding ladder you could climb to get leather-bound books.
The floor was bright white marble, making you feel like you were walking on ice. I marveled at his home, thinking this is all I ever wanted in life: something fancy to call my own, that I could host parties at. I stopped short of thinking it was “showing off” but that’s what I really meant.
One room was a shrine to his teenage daughter, who was already a successful musician and moving to Nashville to further her career.
“Have a seat! Make yourself at home!” he said, gesturing to the huge couch across from me.
I still had the satellite phone in my hand and assumed I’d be dropping it off and leaving. I didn’t expect this visit to be a whole “thing”.
“Do you want a beer?” he said, giving me a joking wink, knowing I had to go back to the office.
He sat down and we chatted about life and business. I was in my full business attire, while he sat across from me in a disarmingly casual outfit. A wall of luggage sat just to our right near the front door, watching us impatiently as we delayed his departure to the airport.
“You’ve done a good job, Sean. I just want you to know that,” he said with sincerity and a strange sense of finality.
“Thank you,” I said, unsure of what the out-of-context compliment meant.
He paused, then said, “I’m leaving the company in two months. I’m retiring.”
This is when my jaw dropped.
“You’ve got to be kidding me,” I said.
Dan was six months away from a huge buyout that would grant him a $30 million payday, a record for the company, and even our industry. This wasn’t a shady paycheck, scalped off the back of hard working employees. He’d legitimately grown the company by huge margins and benefitted both our workers and our customers.
“But what about the deal closing — ”
And before I could finish, he interjected and waved his hands, “I don’t care about that.”
He said, “I’ll be honest. I’ve been miserable for a long time. I climbed all the way to the top of the corporate ladder, only to realize it was propped against the wrong wall.”
“I mean, it isn’t a terrible wall,” I said, playing devil's advocate, “It has certainly provided you with a nice lifestyle, right?”
“Well, not really,” he said, gesturing to our surroundings.
“I’ve missed so many recitals, dinners, family gatherings, important moments that I can’t take back,” he said, with noticeable regret.
I should have just shut my ignorant mouth at this point and listened. But at this stage of my life, I was so ambitious, so fixated on money and upward mobility. It was my entire broken identity.
I shrugged and said, “But why stick it out for another six months? Forgive my candor but that’s so much (money) to leave on the table.”
“This bonus would be no different than the others. I’ve made so many decisions like this prior. I was always one project, one week away from another big career win. I’ve had enough wins already. It’s time to live.”
It was jarring to hear a career hero of mine speak with such vulnerability, revealing what I perceived as weakness at the time. This twisted, sharkish part of me thought, “He can’t take the heat.” He seemed so impenetrable at the office, so without flaw. All this time, he’d had his eye on the door.
Dan was so good and dedicated to his job. It was hard to imagine anyone filling this void.
We spoke for a few more minutes before I left. I stared vacantly on my drive home, with my hands draped over the steering wheel. It was the first time I began questioning if I was making a mistake with my life. Was I chasing the wrong rabbit? If this president, who’d done everything you could dream of in their career, was suddenly regretting all of it, would I face this same dilemma with even a modicum of his success?
Our conversation burned into my mind over time. And the questions didn’t stop. What if the dream I’d built up in my mind was a mirage? I’d spent so much time hedging risk for our company, but why wasn’t I hedging risk in my own life?
Where I saw all of Dan’s trophies, his mansion, beautiful wife and nice cars, Dan only saw missed moments with his family, time helping his kids with their homework, and supporting them at recitals. These were all things he could never buy back or reclaim through time. His focus on money had cost him so much. It’s that fact in particular that sits in my mind.
I suspect more of us would benefit by thinking about regret, and how it might manifest in our later years. A little due diligence might go a long way. This isn’t to say the corporate success and personal regret are intrinsically related , but more that balance and intention should be respected as important aspects of living.
I’ve learned to never underestimate the power of a good conversation with someone more experienced. It’s often a catalyst to growth.
Dan was always the king us younger employees thought ourselves as. But sometimes, the king needs to hand in his crown, and that’s when he will truly be free.
Through happenstance and fate, I ended up working for or with some very wealthy people, either for them providing in-home IT services or with them as board members or major donor development in nonprofit organizations. Their lives genuinely made me sad. Only one of them truly seems happy, and he has eschewed the trappings of wealth. He's worth billions and lives in a 1990's 3 br/2 ba worth about $250k. He drives an old beat up truck or bicycles everywhere. He and his wife have been married over forty years and are so down to earth and happy.
The rest of them? Miserable. Lives full of drama, chaos, and unhappiness. They self-medicated with alcohol, food, drugs, and sex, in which they could indulge at a moment's notice. I always left their homes SO looking forward to driving to my modest little house with my children waiting- our happy little nest. I've never understood it, the quest for riches. Enough money for stability? Sure! But grotesque wealth? Nah. Seems like a huge headache.
I loved reading this. I retired relatively recently but have a habit of regretting the past. My brain, when it wakes up in the morning, simply locks on to the past and what I could have done better, and analyzing decisions I need to make about the idea and the rest of my life. I am free of many time sucks, but time is STILL a constraint!
But to my point here: this post about the wealthy and successful executive who finally moved on sharpens the reality that there is so much more to do, so many other passions to pursue once we're free of needing to make money. Once we become entrepreneurs or retire, we have to be self-starters, create our own schedules. Above all, pursue a personal passion as well as support and be present for family and friends.
OK, a bit rambling above, but I hope you like it!