I worked for a billionaire once. He had his own private island, which he’d named after himself. It was on a lake far up north, a place you could only access in summer. He occasionally hosted offsite retreats for his various staffs on this island, events the company considered a perk.
Attendees for these retreats arrived by boat. Once there, we’d discover plates and glassware with the billionaire’s name engraved upon them, a room dedicated to storing cases of his favorite potato chips and a sprawling outside coop filled with a half a dozen or so heirloom chickens. The billionaire’s young children had given the chickens names, like you would beloved family pets — “Fluffy,” “Spot,” “Sparkles.”
When he took us on a tour of his island, someone asked what happened to the chickens in winter. Without blinking, he told us he simply left them there to freeze, bought new ones the next season, gave them names too. “You walk away,” he said. “and let nature do its thing.”
The billionaire had a young pretty wife, homes in many states and specific rules for living that everyone around him followed to a T. Still, he didn’t seem particularly happy. Decades before he’d been the kind of money shark who made the kind of smart money moves that land a person like him a fortune. But he’d seemingly made few smart moves in years. His multiple businesses — especially the one I worked for — were now cockamamied, irrelevant and out of touch. None of the strategies he urged us to employ were realistic, few even made much sense.
The billionaire held court over yes men, asked many wrong questions, refused to be told “no.” He clearly relished the power of his C-suite title, throwing his weigh around. I only witnessed one of his startups/ego follies up close, but it was clear this was no longer a man who should be in charge. It was also clear that — unlike the callous, all-business approach with the chickens — he would not walk away. The business I worked for went under within two years.
In the past few weeks, I’ve been thinking a lot about what it means to walk away (it’s even a theme of this week’s Everything Is Fine), about how and when we shift from big, ambitious positions into quieter lives — and why. If you follow politics or news of any kind, you know I’m far from the only one with “stepping aside” on my mind.
Last week, the Atlantic featured a conversation with Arthur C. Brooks, an expert on leadership and happiness who wrote one of my all-time favorite articles about aging and work. In the interview, Brooks was peppered with questions about Biden and the trap of staying too long. He also talked about the “war” between his own prefrontal cortex and his limbic system when he himself walked away from a big job in his mid-50s:
“Some scholars believe we have four fundamental human needs: belonging, self-esteem, control, and meaningful existence,” Brooks explained. “When you step away from a high-prestige job, you risk losing these […] My limbic system, specifically my dorsal anterior cingulate cortex, which is dedicated to resisting ostracism and rejection, was fighting me, saying, Don’t make these changes, because you will become no one.”
Brooks goes on to describe how the professional roles for which our brains (and hearts) are ideally suited actually change over time, that the power of highest-up positions isn’t right for us through all stages of our lives. Finally, he landed on this paragraph, which hit me like a punch in the ribs: “For all successful people, there comes a time to decide between being special and being happy. Being special—staying on top—is hard, tiring work. But it is an addiction, which is why people keep at it way beyond what seems reasonable, at great harm to themselves and others.”
In my many, many years working I encountered a series of leaders like the billionaire, those who kept at it far beyond that which was reasonable (and, before I was fired, I was maybe on the road to becoming one myself). Bosses who were stubborn, who seemed stuck, who clung to positions they were either no longer up for or enjoyed. Those who stayed because they were too afraid to let go— of power and titles and salaries, of course, but also of how, because of their jobs, the world saw them and how it made them see themselves.
To be clear, these bosses were people of all ages. Relevance and skill doesn’t necessarily shift because we’re old, but because we’re not engaged and curious in whatever we’re doing, because we’ve been there and we’ve done it, because our ego is caught up in a dated idea of who we are, because even if we know intellectually that whatever we’re in isn’t working, we’re somehow sure the next thing will be less good.
I’m not a scholar like Brooks, but I have learned this: the biggest mistake many of us make when considering walking away is to focus on what we’ll lose, instead of imagining everything — the time, opportunity, freedom and, yes, happiness — we could gain.
After establishing success and power as an addiction (and by extension, as my book argues, workaholism and compulsive ambition), Brooks ended his treatise like this: “Get sober; be happy.”
I’ll drink (a crisp bitters and soda) to that.
***
My book Ambition Monster is out now. It is, I’m told, a good book.
The chickens! The causal cruelty! My hope is that a housekeeper or other staff member took them home and they were laying eggs for kinder people. His businesses failing was Chicken Karma.
Yes! This is something I grapple with a lot; thank you for putting it into words - being special vs being happy. At 50, I have a solid job that pays well, and I work with people who like and respect me. There are stressful days, but generally I am able to take time off without everything falling apart. Overall, it affords me a very happy lifestyle. But this job is not really special, not in the way my 22 year old self set out to be. I sometimes worry that I settled, I worry about what happened to all of my ambition. But this worry is so silly, because I’m happy! When I look at it this way, I don’t need to be special anymore.