Common Projects Chelsea Boots

What does it mean to be a boss?

Despite what Human Resources would have you believe, there is no one-sized-fits-all approach to working with people. People are always lauded as being the most important asset a company has, yet people are terrible at treating other people well. It’s why we all work too many hours. We’re so worried that we won’t be seen as some sort of corporate ideal of an employee. We’re expected to sacrifice, dig deep, be strong, but at the end of the day, we’re simply expenses on a balance sheet when it all comes down to it.

We have little to no training in this country on how to be a boss, outside of management courses at MBA programs, which are mostly BS, and no replacement for the real thing, which is actually looking someone in the eye who wants you to tell them what the plan is, what to do, what the end goals are. Who wants you to be honest when them, when many times it’s much easier not to be.

What we do have, by the pound, are ideas of what a boss is. Of the man across the desk pointing his finger at you: “You’re fired!” (which in real life rarely occurs. Human resources exists for this very reason.) Of the woman chucking her coat at you with hardly a dismissive glance. Of Tess lacing Katherine’s ski boots, while she flexes on the phone in German. Of Michael Scott, and J. Peterman, and Bill Lumbergh. You oversee people, and have responsibility, so obviously there must be something special about you, the thinking goes. And one does enjoy getting high on one’s own supply. “Who’s the boss?” You think. “I am!”

It would be better for everyone if we didn’t think that way. You may be good at your job: analyzing data, or dreaming up campaigns, or teaching first graders, or tending to patients, but chances are you are not very good at managing your team. Why? Because people are the hardest thing. It’s hard to tell someone that a project, or a deck, or a proposal, or anything they’ve worked really hard on isn’t quite right. It’s hard to tell someone how to improve in certain areas without making it personal. It’s hard to deny someone what seems to be a completely reasonable request because of matters of corporate policy. To paraphrase Bobby Cannavale, it is personal (or personnel!) They’re people, ain’t they?

I have been lucky and had some very good bosses. Bosses who knew how to give truly constructive feedback when I’d botched something. Bosses that saw me as a complete human being, and not a cog in a wheel. Bosses that trusted I would do a good job, and supported me in the ways they knew how: listening to a problem, and proposing a solution, or helping me around an obstacle. Who helped me focus on what was important. Bosses who have been sincere in their efforts to see me grow. I’ve also had terrible bosses; ones who gave no direction, or leaned on me emotionally. Sometimes the great bosses and the terrible bosses were the same person; after all, bosses are people too, and as complicated. And, I had one boss who was so terrible that he probably derailed me for years, an experience I’ve chosen to take the long view of, since I’ve certainly come out the other side a much better person… and a much better boss myself. But I am still resentful.

So what has any of this to do with shoes? And these shoes in particular?

I bought these boots to be a boss in. After quite a bit of searching, I had finally found a new job. I had loved my old job. It had been extremely corporate and buttoned up, but I was very lucky and had a series of great bosses there, all of whom I learned so much from. I worked with smart, kind, well meaning people across the board and my direct reports were all wonderful. Each and every one taught me so much, especially about keeping an open mind, and letting people try things, whenever possible. But the job itself was getting rote, the issues to solve were the same, and I wasn’t growing any more. It wasn’t good for me or for the company.

I knew what I wanted in the new job; a challenge, an opportunity to build something wonderful with a great team, to find meaning and purpose in retail (don’t laugh!). And I knew exactly what I wanted to wear to do amazing thing; something sleek, something flat, something elegant, yet with a bit of an edge, a touch of tough. Black, of course. I thought I wanted lace up boots, but when I laid my eyes upon these Common Project Chelsea Boots, I knew they were it.

In them, I would stride into the office, a leader, someone to be listened to on bended elbow. The boots butched up dresses, and dressed up jeans. I could wear them to present to the CEO and to lunch with agencies and on planes to meet with our partners, some of whom were celebrities. The boots were powerful in their simplicity; a show of strength. They said, “the person that wears these knows elegance and design. She has no need to crow. She is secure.” I could wear them everywhere. In these boots, I would be smart and strategic and strong.

And for six excellent weeks, this was true (sort of)! I loved getting to know my new team. Each of them was smart, dedicated, and hardworking. They all had ideas and wanted to grow. Some were easy- give direction and watch them run. Some were hard but worthy; talents who didn’t quite understand the lay of the land but trainable. I have a soft spot for people like that, of course I do. Those women reminded me of me. Of all the mistakes I made coming up

For instance, once, when I worked at Seventeen Magazine, I was sent to cover a press event launching Raquel Welch’s wig line. It was at Asia de Cuba, which in 1998, was the absolute coolest place in New York. I drank Cosmos and ate tuna tartare in little wontons, while getting my wig styled and chatting with Raquel herself. On the way out, the PR person offered me a file filled with information about the line. “Oh I don’t need that,” I told her breezily. “Why would Seventeen write about wigs?” This may have been true but it was a gaffe of the first order. I know, because the next morning my boss, Liz Brous, the Beauty Director, who was referred to by all as “the nicest person in beauty”, pulled me into her office, and gently scolded me, which means that the publicist must have called. She was kind, clear, and firm as she explained that I should have taken the folder. I was right, we wouldn’t cover it, but the whole point was the consideration. In the consideration, was the grace. And besides, that publicist worked on accounts we would want to cover, and maybe want the first crack at. I was horrified. I was too green to understand how small the world is, a lesson, by the way, I am still learning. Liz’s talk has always stayed with me: to be clear, thoughtful and kind when dealing with mistakes, my own and others’. We all make them. It’s in the cleaning up that we show who we are. And also to be able to laugh. I have always thought of Liz the gold standard for bosses.

Much as I’d like to think I’m a great boss, I’ve definitely made some mistakes, of course. Probably more than some. Trying to dance around an issue and then ripping the band aid off with a blunt knife. Hoping that if I don’t bring something difficult up, it will just go away on its own (because this sometime does happen!) Getting aggravated or not giving clear direction about what was wanted and why. I do dread yearly reviews, even if what I have to say is positive (which I’ve been lucky and it has been.) Once, I had to fire an assistant on my team, who had become a very good friend. That was terrible. We are still friends, which means so much to me. Not so long ago I had a headsmacker of a moment, when I didn’t give someone enough credit for their experience, and could feel how condescending I was being. The one thing I realize works best sometimes is to shut up and listen to the vent before trying to solve the problem. By nature, I tend to jump ahead to the fix. But people want to figure things out themselves. What they want from their boss is to feel heard and supported.

Back to the shoes. The pandemic hit. That rather intolerable, formerly bossy person that was me, the strider-into-of-meetings currently has no place to wear these boss boots. And has a creeping sense of insecurity. The world has come crashing down, hasn’t it? Not just for me, but for everyone, which is a cold comfort. But there it is, a fact of life.

There is no answer in the boots. Only the dreams of places to wear them. Will I be a boss again? Do I want to be? I’m not sure. But the boots will still be good.