The One Thing No One Tells You About Being the Boss

When I was younger, I used to think life at work would instantaneously, even magically, get better if only the boss understood a few key things they seemed completely oblivious about. Young and naturally endowed with all the answers, it was all too easy to think of ‘the boss’ as an old, curmudgeonly, greedy, and poorly informed individual. A boss was someone who didn’t understand me, my generation or the size of the ever-widening generation gap; marked by differences in net worth, ideals and even ways of living. Playing into the timeless rolls espoused in the classic Christmas Carol, I was clearly the industrious, easy-to-love and pure-hearted Mickey Mouse, which meant my boss, no matter who, was the nefarious, greedy, and ill-tempered Scrooge McDuck.

Dreaming of Utopia 

As the storyline goes, I was fated to suffer long enough in hopes that one day I would earn and then be given a chance to run the place myself. When that time came, I knew I wouldn’t simply run it the same way as my former boss; after all, I was no Scrooge Mcduck. Thinking what this new world of work would look like, I’d allow myself to drift into an idealized place, a sort of workplace utopia. In this place, everyone would be happy, paid fairly, and utterly aware of the weight and value of each other’s contributions. Work would hum along naturally, smoothly and, of course, as efficiently as humanly possible. Free loaders wouldn’t exist, and everyone would be good at their job.

In my utopian dream, the market would always act fairly, predictably, and in everyone’s collective favor. Greedy miscreants would be immediately punished, and together we’d build a world our ancestors would marvel at and our children would talk about for eons to come. Clients, employees, partners, and vendors would all easily be able to express their wants and needs, and everyone would unanimously agree on what was fair. Always. None of us would ever work on holidays, and we’d all find brilliant solutions to the inevitable and ongoing problems encountered through all of recorded history.

Along Came Reality 

My thinking continued along those lines, permitting myself to go on believing that this world was possible, if only Scrooge Mcduck got out of the way. As my career progressed, and I quickly found myself on the other side of the equation asking my younger team members what they were looking for, what they wanted, and what I and the other managers could do better, I couldn’t help but laugh at my earlier naivety and the world I had thought so easily possible.

In those earlier days, it was all too easy to ignore the fact I couldn’t really express what I wanted, while simultaneously expecting those in charge to know and meet it quickly and painlessly. Now older, and somewhat wiser, it was all too easy to see how hard it was to make everyone happy, when what they expressed they wanted often ran in direct opposition to other considerations.

Where I Learned the One Thing 

As I wrestled with this age-old dilemma, I was fortunate enough to have a close relationship with a mentor, a successful business entrepreneur who would eventually sell his company for millions. In talking with him about my problems, it wasn’t long before he was laughing. Worried he wasn’t taking me seriously, I began emphasizing the points I thought he was glossing over. Eventually, he curbed my agitation by cutting me off, and saying: “Being a leader isn’t really much fun, is it? Sure, there are some sweet perks, but no matter what you do, someone is always upset. Someone is always angry.”

He then made his point: The one thing that always surprised me about being the boss was how differently everyone treats you. People stop sharing things with you freely, because they are worried you’ll fire them, fire their friends or something worse. When I was younger, like you, I wanted to lead, but I didn’t realize it would also come at the cost of being different, at no longer being like everyone else. That’s the one thing they don’t tell you in business school — being the boss means you don’t really get to be anyone’s friend anymore. After all, you sign their checks…you can’t really be friends with someone who signs your checks. Most people are inherently good, so they try to be your friend, but they can’t. At the end of the day, paying their bills is just more important. Plus, I’ve had to fire my friends before. It’s not fun.

It’s funny though, he continued, when I was younger and still learning the ropes, I used to dream about this sort of fantasy business, too. The one you described earlier, where everyone gets along, likes each other, etc. It can be like that sometimes, but then life happens. Someone moves, gets pregnant, gets a new opportunity somewhere else. Life changes, and it’s those changes that bring in the friction, the frustration, the problems. It’s also the changes that make it all possible to begin with.

And What I Learned 

My mentor understood how tempting it is to wish for utopia. But his wise insights taught me to stop dreaming about how it could be perfect. Instead, he advised, just focus on taking care of your people. They will take care of the problems, if you take care of them. And maybe, think about sharing some of the issues, struggles, and problems you’re wrestling with at your level. Sometimes transparency is a great way to encourage people to work together. Also, get started making friends with the other leaders. They are likely just as lonely as you are, and you’d be surprised how much can change when you and the other leaders are in agreement.

Written by Sean McMann.
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