In my mid-thirties, I was put in charge of a staff of about 50. One day I was tossing a Nerf football over the tops of cubicles with my colleagues, and the next I was driving to work in a company Lexus, saying “Good morning” to a solicitous personal assistant, and closing the door to a corner office. The strange thing was, I had far more anxiety about convincing my employees I was still cool than I did about filling my expanded britches. I didn’t want them to see me as The Man, despite the fact that I was, really, The Man. I was shambling toward 40, hoping to pass for 27, 28 tops. This was a mistake.

Kurt, a New York restaurateur, found himself in a similar position when he was around the same age. “You think you can run a business the same way you hang out with your friends,” he says. “Especially a restaurant, because you are sometimes hanging out with your friends, but if you take that same attitude to hiring, salary, and judging talent, you end up with a staff of very hot women who screw everything up.”

For me, a full day of not acknowledging my new title meant playing a lot of computer games with my underlings, freely passing on scandalous office gossip, and generally allowing for the complete erosion of the boundary between supervisor and employee. Staffers felt free to come into my office to watch MTV, grab a soda from my refrigerator, and ask for raises—constantly. I gradually began to realize that by striving to be a cool boss, I had become a non-boss.

I wasn’t alone. Legions of dudes who grew up believing that Guns N’ Roses would still be together if Axl hadn’t been such a tyrant become non-bosses upon corporate ascension. They style themselves as bros who just happen to have way bigger offices, fatter salaries, and not quite as much time for interoffice prank calls. Archetypal non-bosses like Dallas Mavericks owner Mark Cuban, Def Jam cofounder Rick Rubin, JetBlue CEO David Neeleman, and Maverick Records CEO Guy Oseary have reputations for eschewing hierarchy and fostering a sense of equality. Trouble is, those of us who aren’t running a company that’s a household name can’t really afford the risks that come with freestyle managing.

Dov Charney, the 37-year-old founder of T-shirt giant American Apparel, sums up the downside eloquently: “If there is an environment of freedom, mistakes happen and boundaries get crossed,” he says. “Some people can’t deal with all that freedom. It confuses them.” Charney should know—he has been the target of three sexual-harassment suits brought by former employees.

You may not be wandering close to that precipice, but unless you put distance—physical and emotional—between you and your kingdom, you will end up a slightly less ridiculous, better-dressed version of Ricky Gervais’ character on The Office: an unctuous drip who doesn’t earn his employees’ respect or friendship.