A Conversation With Hemingway*

Edward Hopper New York Office painting
Edward Hopper “New York Office”

A few weeks ago a coworker and I headed back to the office together after an offsite meeting.

His name was Hemingway*, after the writer he said, but his livelihood was in film. The short, thirty second variety – TV Commercials – TVCs or “spots,” as the industry has designated. He was an accomplished but not quite famous freelance director. 

“What did you do before this?” he asked.

“I wrote blogs for startups,” I said, and not wanting to dress it up and only down, “Basically, I was a content mill.”

Before that, I explained, I was in graduate school for creative writing. The usual pleasantries followed. Oh what kind of writing did you do? Oh? Nonfiction? Is that like journalism? And after the realization that yes I do have poorly defined (and seldom executed) creative leanings, the usual question if it’s apparent I’m not yet known or paid for my writing:

“So…what are you doing in New Business?”

“I got lucky, I guess.”

He chuckled.

“Do you still find time to write?”

Another coworker – a creative type as well – caught up with us as we descended into a Midtown subway. It was the same subway I took each morning, but we were approaching it from the other end and I found myself disoriented – until I saw the same poster of an expired Degas exhibit in front of which I waited each morning.

I thought about the last time I wrote. In this blog, in my red diary – the last entry of which is dated 2015 -, the last long, ambitious email to a friend… The days blended together and I remembered the weather being cool the last time I picked up the proverbial pen. As in, I believe it was early spring. I thought too about the days I found freedom from work an hour early but chose to have a glass of wine and then another followed by dinner with friends, or “unwinding” with an 1.5 hour long episode of “Inspector Morse” rather than sitting down to write or even read. I measured a longer gap than I was proud to admit. I answered honestly.

“I find the time, but I don’t write.”

“Argh,” said Hemingway, “I know the feeling. I’ve been struggling with it for the past 9 years. Should I stay freelance or go full-time.”

Our other coworker laughed a knowing laugh.

“Yeah, I made the jump a few years ago and I can tell you… my own projects seem like a distant memory.”

“That’s what I’m afraid of,” said Hemingway, “I like the freedom of freelancing. And nine years since I’ve started, I feel I’m at a place where I can more often than not pick and choose my projects but…”

The train rattled in. Hemingway ran his hands through his hair and shook his head in a rote, well-rehearsed pause – it was a conversation he’s had many times, with many friends, with many other creative types – “at the end of the day it’s still a hustle and I’m still scrambling for time to work on my own shit, wondering if it’s worth it because, well, I don’t know.”

“You know what they say,” our colleague said as we stepped on, “Once you go full time you’ve basically surrendered.”

The train started. I wondered what people thought when they saw the three of us talking. “Creatives,” dressed in varying degrees of professional dress, the two tall men in their checkered button downed shirts and jeans, beards and canvas messenger bags. The Asian girl with her black leather bag and black slacks and cream silk blouse. All three looking somewhat tired. All three bearing expressions of subtle, latent discontent. Three young professionals on the subway, on the way to work, talking about work, wondering about the possibility of their other, more important (?) work.

We were quiet for a while. Past 42nd and 34th street, after which I looked up.

“No,” I said, “It feels like that, but it doesn’t have to be like that.”

I didn’t have examples off the top of my head – though I guess J.K. Rowling would have been a convenient one – and it would be a few days before I read this “parable” of Borges , but I felt that our colleague was different from Hemingway and I. At least for the time being.

A few years ago I might have framed it with more drama. Oh look at the failed, embittered artist who has sold his soul to the Corporation! Let his tired face and hollow eyes and abdominal beer pudge be a cautionary tale for all those who put their dreams aside!

But I’ve just turned 30 and have been marinating in a rather thick stew of reality.

Money! It makes the world go round. It pays your rent and buys your wines and dinners and magazines. It pays for flights to far off places and buys gifts for your parents and lovers and children. Puts smiles on people who make you happy, including yourself.

I get it. I’m working now too and I’ll be damned if I have to scramble for health insurance again. For the first time in six months, I’m not too concerned with needing to see the dentist. I might require $10,o0o worth of fillings but at most I’ll need to cover 20%.

Instead, I just hoped our colleague – Fitz, I’ll call him – would eventually use the time he has to do what he wants. If in fact it is what he wants.

That’s the other thing.

“I know, I know,” Hemingway said, “That’s my fear too. Is that if I don’t make time for it, it probably means I don’t want it enough.”

The train stopped at Union Square and slowly, with the rest of the late-to-work crowd and the freelancers looking for hip cafes to work in, we filed off. I walked behind them, then up the steps I take each morning to work, through the turnstiles and up again, through Union Square farmer’s market, the light hitting me in a different way because it was a different time of day.

We quietly made our way back to the office and quietly up the elevator, where we peeled off into our separate corners and sat down, almost relieved, in front of our work computers where what we wanted was never the question but what was it the client wanted. By when? For how much? And for how long? Easy questions, in the grand scheme of questions.

The hardest one throbbing in the back of our minds: how much do we want it?

*Name changed, though he was actually named after another famous (and dead) writer.

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