Simon Stone is an investment banker who hurt me, likely without knowing how much he hurt me.

Simon works more than 100 hours on bad weeks. He has never tried eggnog, he has a group of work friends that he seems to adore, and he keeps a mini fridge in his room solely for the purpose of storing cans of Celsius.

I’ve been surrounded by people who work on Wall Street for most of my life, but I rarely interact with men in finance who are around my age. Simon, being just a year older than me, taught me a lot in the time that we spent together.

“When I leave something [behind], I’m done with it.”

I once described myself as someone who lives “in the past and present simultaneously”. I am constantly thinking about and drawing upon my experiences from the past. I know that this isn’t a particularly novel concept. It’s how all human beings function to a certain extent. After all, how would any of us ever learn any skills if we couldn’t draw upon our past experiences?

But there are many things—many memories and many facets of who I once was—that I wish to leave behind but can’t. Because I still live there, in the past. I often forget that being done with something is an option, and he reminded me of that.

But how did Simon do this? How does he manage to leave things behind without ruminating on them much later? How does he not miss things? I wish I could ask him these questions.

“Join a running club…I hate running”

This was Simon’s suggestion when I asked him how a person who’s working from home in the city can make new friends of different backgrounds.

How can I meet people who aren’t just different flavors of the academic and professional maniac that I am? How can I establish meaningful friendships with people who aren’t from my alma mater or my hometown?

He hates running (and I hate running too), but he suggested joining a running club to meet other people. Not a bad idea. Do they have restaurant-hopping clubs, though? Because I’d be more inclined to join something like that instead…

It’s okay to fuck up at work, and it’s okay to be honest about that, too.

A lot of our conversation revolved around work. And at one point, I explained to Simon that the reason new engineers like myself often work long hours is because we’re new. We don’t know what we’re doing. I wondered, very briefly, if I had portrayed myself as an incompetent engineer by saying that.

However, later in our conversation, Simon explained, without a hint of shame, that he makes mistakes at work. He talked about how a client “probably thought [he’s] stupid”, and this didn’t seem to bother him at all.

A close friend recently wrote that she realized that “calm confidence comes from competence” while talking to me, and I thought of this sentence while chatting with Simon.

Simon exuded a charismatic form of confidence when we were together. He admit, repeatedly, that he is new to his job, and that he makes mistakes. And I couldn’t help but admire him for it. He has a refreshing air of honesty and humility that made his confidence seem more genuine.

New grads fuck up all the time; it’s expected of us. And it’s okay to admit that in conversation with each other.

“I don’t do it for the money.” It’s okay to love working. It’s okay to chase things.

I need to be working on something or towards something or for something to stay sane. I take the pursuit of professional and academic excellence to extremes.

This personality type is great for accomplishing feats that look good on paper, but I often wonder if I should allow myself to behave this way. Why do I want to work so hard? Wont I drive myself to burnout? Should I try to change this aspect of myself?

Simon admit that he’s also intense about work (which I suppose is to be expected in a person who goes into banking), and he offered a very refreshing viewpoint. He explained that he isn’t necessarily working to eventually have a certain amount of money, and he, like me, has no interest in retiring early. (“Retirement,” he said, “just seems like waiting around to die.”)

He works this hard because he likes working hard—he needs to work hard. And this is okay because it’s fulfilling for him.

And despite his workload and crazy hours—despite the fact that his role requires him to be on call around the clock—he seems to have found some semblance of balance. He has friends, he travels and explores the city, and he makes time for his other interests.

This conversation made me think that maybe it is possible for people who are wired like me to have it all.

“I don’t think people realize how hard it is to run a company”

“We’re risk-averse,” he said. “It’s easier to have other people take the risk for us.” And I couldn’t agree more.

I have a type-A personality, and judging by our interactions, I suspect Simon shares a similar disposition.

I’m very opinionated, and in professional and academic settings, my natural tendency is to assume leadership roles to rally my peers around my visions.

For years, I envisioned myself stepping into people management roles, and my mentor figures always expect the same.

But in the past two years, I’ve watched several people that I know step down from C-suite positions after less than 10 years on the job. I was shocked by how quickly the magazines and newspapers that once celebrated the new executives turned against them, casting people who I know to be exceptionally intelligent and kind as inept or evil.

It's been a sobering realization of the burdens associated with joining the executive team of a prominent company and living under the scrutiny of the media. And it was comforting to hear that someone else my age, who feels passionately about work, felt apprehensive about stepping into leadership.

Maybe it’s okay to enjoy being a small cog in the machine. Maybe it’s okay to love work for the sake of working. At least for now.

Live downtown. It’s quieter.

It’s much quieter than midtown, at least.

Simon did, however, point to a raised median with a few trees and a walking path and call it a “park” several sentences after asserting that downtown is the best place to live within Manhattan. So perhaps I won’t be moving very far down.

I would miss the plant life and crisp oxygen dearly.

---

There are so many things that I wish I had asked him about and never got the opportunity to.

Maybe I’ll get a chance to chat with him again one day in the future.

Or maybe I never will, because he has left me behind.