I Was The Lonely Workaholic Boss. Here’s What I Learned.

I’d just been promoted to a managerial position after years of hard work. I’d been a grunt financial analyst, grinding my way through endless recurring tasks, externalities, changing priorities, difficult clients, and was eager to do something bigger and better. This was my moment.

Almost immediately after starting my new role, I noticed a huge shift in the social dynamics at the office. I’d been so friendly with my coworkers. We did lunch together all the time. Then, immediately after the promotion, things got weird. I was now in a position of power, with these same friends reporting to me. Their behavior changed and some even appeared nervous around me.

I realized I needed to maintain some distance from them as well, as my position could require me to drop the hammer. But the change wasn’t welcome and left me feeling less satisfied with my job.

Perhaps it is as William Shakespeare wrote in Henry IV, Part 2, “Uneasy lies the head that wears a crown.” The line is spoken by a 15th century English king, who is tired, sick, and alone, with his isolation a result of his power. And granted my own dabbling in power was far, far smaller, I suddenly felt that same uneasiness. I found myself staying later and later at the office, and feeling increasingly distant from my coworkers.

This exact pattern tends to get more extreme as one moves up the ladder. A study by the Harvard Business Review found that half of CEOs are lonely on the job, and that loneliness impacts their performance. It is also correlated to quicker burnout on the job.

The socializing problem I experienced comes with how people perceive and enjoy activities. Famed psychologist, Daniel Kahneman, ran a well-known study in 2004, surveying women on their experiences from the prior day’s work. He asked them to rate activities from most to least enjoyable.

The women reported most enjoying socializing, making love, relaxing, and spending time with friends and family. They least enjoyed working, taking care of kids and commuting. But their absolute least enjoyable activity? Interacting with their boss.

It’s too difficult to have a friendly, buddy-buddy relationship between boss and employee. Both of you know the arrangement is anchored in judgement, with the boss constantly having to assess your performance. Their aversion to dealing with you can be palpable, and affect your own job satisfaction.

Compounding this, I found, as many long-time managers already knew, that work became all demanding, and often quite lonely — which felt strange given how my calendar was suddenly filled with meetings.

Some weeks brought long hours that had me in a giant office alone, and walking through a dim, empty parking lot, feeling like I was carrying the world on my shoulders. I woke up from stress dreams and went to work with my mind swirling the myriad problems I needed to solve. Over time, I learned the loneliness was really a product of workaholism, which is an increasing problem in the US, and is rooted in an irrational fear of failure.

It wasn’t a happy time in my life, nor is it for many like me. Which is why I eventually quit. And I would caution those still living it, to consider if it’s worth working that 61st hour that week. Ask yourself, “Is this extra three hours really making the difference?” I found that I often lied to myself about the hours I was working, kidding myself into thinking it was necessary and not a problem.

Escaping loneliness even if you aren’t a boss

These days, I am just a humble writer — but am faced with the same loneliness problem. This profession is quite isolating. I do all of my work from my home office. There’s no hybrid work weeks, no weekly calls, nothing. It is just me. Some days, it can feel like I’m the last person on Earth.

Which is why I’ve had to take the extra step to network with other writer friends, mainly through Slack — as writers are a rare breed and often scattered around the planet. But even the mere act of seeing other writers periodically for dinner, having a phone call, or zoom call to catch up — works wonders in putting me in a better mood, and reminding me that there are others out there like me.

Whether you are a grunt level employee or a CEO, it’s often easy to find friendships with relative peers. My father rose to vice admiral in the Navy before retiring, and carried incredible burdens and stresses that only war can bring. To this day, most of his friends are either long-time friends, or fellow retired admirals or generals. There is a hard-to-replicate comradery that comes with sharing a life path with others, and it can pave an easy path for friendships.

Ben Franklin faced a similar problem and founded the Junto Club in 1727. It was an informal group of men, who were all of similar stature and responsibility, and without peer in their regions. It was founded less on the premise of elitism, and more to have others who could attest to and understand the problems they faced. They met and organized discussions, with a list of business questions that each man faced in their endeavors. These interactions brought great satisfaction to all of the men and attendance remained high.

It might seem counter to the prevailing wisdom that one should keep work and personal affairs separate, but having a sense of friendship at the office is quite important for happiness. A study by the advisory firm Future Workplace, found that 90% of people said they have friends at work, and 70% said friendship at work is important for a happy working life. Even further, they found that people who have a best friend at their job, are twice as likely to enjoy work.

Some of my closest work friends are writers. We privately chat about our frustrations, side projects, and creative blocks. We exchange feedback and talk about the future. As a group, we tend to be exceptionally introverted, which is why it’s so incredible that we all still pine to have a connection to each other, and naturally gravitate into groups where we chat and bond.

It has taken me some years to realize the importance of these social-work connections, and to value them as friendships to the extent that I can. But as the adage goes, better late than never. Loneliness can easily accompany success. But there are steps you can take to counter it. Don’t go it alone, folks. There are peers out there like you, who wouldn’t mind having someone to talk to.

Above all, remember that being the boss isn’t all it’s cracked up to be.