Goodbye Pants

It only took me about thirty years to come up with a conclusion that I knew thirty years ago.

I am a writer.

However, I didn’t always have this clarity. Or did I? It’s hard to tell even with the benefit of hindsight.

Lou was new to the organization, and he was every bit as intimidating as he was brilliant. He was the definition of a change agent in a title company that would need several more iterations to get to conservative. Lou wanted to change all that and was clear everyone needed to get on board and change their method of thinking immediately.

This came as quite a shock to those positioned above and below me. Not that they were resistant, but Lou was all about confrontation, sometimes friendly, sometimes rough, but always challenging. It was his way or the highway. Lou’s accent and swearing weren’t even necessary to tell you he was from New York.

Where else could he be from?

The fact that we were driving alone after a business dinner was due to our fellow travelers squeezing six into one car to avoid driving with Lou. I relished it up until Lou’s very simple question.

“So, if you could be anything, what would it be?”

The best answer I could think of was also the most vague.

“I want to be a writer,” I offered.

“Then why aren’t you?” he replied without a moment’s hesitation. To be fair, it was a question I often asked myself.

“Fear of failure, I guess,” was my answer.

“Bullshit,” Lou replied in his usual manner of telling you that he always had the right answer. “It’s fear of success.”

I didn’t even know what to make of that, but I thought it was cool that Lou at least believed I could be successful as a writer. In his eyes, and in that moment, he didn’t think any of us were successful. He wasn’t wrong.

I changed subjects as quickly as I could, not wanting to continue a conversation confessing my dream job wasn’t remotely going to be in the field I was currently in.

Then, eight years later, he asked the same question.

Our company was bought out. While the new regime wanted me to stay, I knew immediately that I didn’t want to be there. After all, without Lou and Bob (my direct boss), it wouldn’t be the same place that I grew to love. I had begun my job search and got an offer from the first job I applied for.

Director of Infrastructure for the Chicago Tribune. If I weren’t a writer, at least I could support them.

I decided to ask Lou whether I should take it.

Lou returned to the same question he had asked me eight years ago and reminded me that I’d never answered it satisfactorily the first time.

“So, again, what do you want to do, kid?” he revisited. He always called me kid, even though he was like maybe ten years older than me. I found it endearing, but also wished I had earned enough respect for it to be gone.

I struggled to provide an intelligent answer. I instead went for what I thought was the right answer.

“I want to ultimately be a CIO.” I thought that would please him. By then, he had become my corporate hero.

“No, you don’t,” Lou replied, not missing a beat.

I started to refute that, but it was clear that he was going to provide another lesson, and it was always best to let the Lou freight train roll.

“How old is your kid, about two or three?” he asked.

“Two,” I said.

“And you want to spend time with him, coach him, be a better dad than yours was?” he asked, and I wondered how he knew (correctly) that I didn’t exactly grow up with the Father of the Year at home.

I knew where this was headed and realized I’d already lost.

“Here’s the thing, kid: I have no doubt you can do it, but it comes at a cost,” Lou continued. “You’re going to have to move, spend long hours at work, kiss the board’s ass, go from job to job, and do more of the kinds of things you probably hate now.”

And then he administered the kicker, “And your kids will hate you. Probably Mary, too.”

That seemed harsh, but I sensed he was speaking from experience.

All was not lost, however, as he did say, “My advice? Go for it regardless. Your kids are going to hate you anyway.”

Ouch.

With that bubble burst, he continued to tell me that I still had no idea about what I wanted to do.

He wasn’t wrong. I wished he were.

We continued to talk, and he still gave excellent advice on how I should approach the job offer. He held his arms straight out and explained one arm represented what I wanted and the other was what I had. The best I could aim for now was equilibrium, which of course was impossible since I was missing the “want” part of the equation.

While I eventually achieved some modicum of success, I never did nail down the want.

Until recently, when it became clear to me.

It really came down to the fact that I no longer wanted to wear long pants.

That was something the pandemic taught me. In the year and a half of working from home, I always wore gym shorts. Business up top, party down below, as they say. Pants became everything wrong with corporate life for me. I’m not one of those work from home zealots; in fact, I missed seeing my people in the office, but the simple act of wearing shorts throughout the year resonated for me.

In fact, the first thing I did every day when I got home was pants off, shorts on.

Truth is, there are not a lot of careers where you don’t have to wear long pants. Gym teacher is one, but I already tried teaching and didn’t even like the version that doesn’t require sweating.

Hence, writer.

Now, sometimes when I can’t fall asleep, I replay those two conversations with Lou. In my mind, he asks me that same question, but this time I know the answer.

“I want to be a writer because I just can’t see myself wearing pants anymore.” I state confidently, almost proudly.

He follows up on my fear of failure or success.

I tell him, “Who cares about success? A writer writes.”

Lou looks at me, puts his glasses down his nose as he always did when he focused on friend or prey.

“It’s about fucking time, kid.”

I still have to work on that kid thing.

But this time I’ll do it with shorts on.