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Is being the boss still cool in 2022?


Maybe a better question is: Is being the boss worth it?

It’s an interesting question at this moment for a few different reasons:

1 – Less status when we’re at home and on Zoom all the time.

Back when we were in our offices full-time, being the big boss carried a lot of “status.” What do I mean by that? The bigger–or corner–office, for starters. That carries status in the workplace. Rubbing elbows with the C-suite carries status. A lot of that is lost when we’re working remotely. There’s no corner office. There’s no big meetings with leadership you’re seeing down the hall. A lot of the “status” that comes with the big job has kinda been lost when we’re at home.

2 – Appearances matter (but not when you can’t see them)

One of the perks of being the boss, at least historically, has been the money–because it has the ability to upgrade appearances. A bigger house–where you host holiday parties for your team and show off that home that’s 4 times bigger than my shoebox of a house in So Mpls. A nicer car–you shuttle colleagues around in that Mercedes, which costs probably triple what my Kia does. Or, that power suit–which I see you wearing in meetings every week, which costs 5 times as much as the J Crew outfit I got on the 50% off rack. Yeah, appearances matter–a lot. But, not when we can’t see you. And, certainly not when appearances are being devalued a bit in the age of COVID and Zoom.

3 – Being the big boss means less balance at a time when almost everyone wants MORE balance.

When you’re the big boss there’s not a lot of balance. Ask any big boss. They surely are working evenings. They surely are working on some weekends. And yes, they are working on vacations. This isn’t me speculating–this is me telling you what others in these roles have told me! So, being the big boss means far less balance at a time when EVERYONE wants MORE balance. That may be making these jobs less attractive right now.

4 – The bigger paycheck may not be the lure it once was.

Finally, the elephant in the room. Yeah, the big job comes with a big paycheck. For sure. But, is top pay the lure it once was? Not according to Glassdoor, which says 80% of employees prefer additional benefits over a pay increase. Plus, once you get to a certain level, and you’re comfortable, does that extra 20-30% of money really make a difference? Is it worth the tradeoffs above? For some yes. But apparently, for an increasing numbers, others not so much.

So I’ll ask again: Is being the big boss still cool?

To be clear, I don’t think there’s a right or wrong answer here. Like most things in your career, it’s personal to you. I’m just raising the question based on a number of things I’ve observed over the last couple years.



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