The imperfect boss.


There’s really no better time to write about the vulnerability of being a boss than when you just ended a long, exhausting, in-the-trenches-in-front-of-everyone kind of day like I just did. And when there are super-public moments of you having to call the shots and show up as the experienced yet polarizing leader that you are, you’d better believe that some shame remains long after you’ve taken off your boss blazer.

Today was rough for me. It’s not unlike most days, but it was a bit more extreme. Because I had to show up in ways that required people to trust me rather than understand me. My team is younger than me. I find that it means something. I’ve been in the trenches for a while now. I have so much baggage to my own business. And it’s sort of hard to distinguish experience from baggage.

I might be more sensitive than some. I might be more dedicated than others. But one thing I do know is that I love my team. But I find that hard because I often believe that they don’t like me– or more often– they don’t understand me. I often believe that I’m not good enough for them.

I wish I was at a place where I could do more. I wish I could pay them more. I wish they didn’t have to deal with the shit. I wish I could remove all their pressure and discomfort and growing pains. Because I love them. And because if it’s not solved, it can be seen as a deficit.

Though I have come so far, done so much, innovated an industry here in my city, worked so damn hard, I have no clue if they get it. And the thing is, that’s got to be ok.

Because they don’t deserve my baggage. And another way to say it is that I love them despite business. I love them even when the thing they do doesn’t make us better. Even when I’m watching them do something that I believe (because I can’t fully predict the future) is just not going to work.

Today was a tough day. I was imperfect and bossy and bold and scared and good and un-relatable.

And that, my friends is what it means to be a boss. And you know what else? Damn, I love these people. And that’s part of what makes it all hurt. Thankfully. Painfully. Truthfully. I love. These. People.