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  • Writer's pictureBryan Jun

is it possible to be real friends with co-workers?

After you enter the "post-high school world," I cynically separate friendships into three categories associated with our favorite, money:


  1. Friends you pay for - I'm largely talking about college friends in this category that you either pay for through your parents' hard earned money or your student loans. Obviously (fully acknowledging this is an unbelievably cynical view of things to sound witty on this post) you can argue that you've done your part to study hard to end up at such places and the story can go on. People you meet at that new city you move to, acquaintances you encounter while at the bar or that costly hobby you insist on taking on Saturdays for self-improvement all fall in this grouping.

  2. Friends you get paid for - This is a rather unique group that may not apply to everyone, but this is the "client" group. If you're a teacher, it's your students; if you're a sales rep, the people you sell whatever you're selling to; I experienced this as a Resident Adviser wondering how organic the friendships I established with my residents were. If you're on of them reading this, you know I've said this analogy every other day!

  3. Friends you get paid with - This is the categy I'd like to focus on for this post and perhaps the selection of folks we struggle with the most, who we call our "colleagues."

Before I go on, I want to ensure you that I'm not this cynical in real life and as many of you that know me well (or have been following my digital journey!) know, I'm very people-driven person. I'd say one of my few inherently "nice" qualities is that I enjoy the company of the general human race, enough so that my daily destress activity in Chicago is to independently walk out into the Magnificent Mile just to be around people. Also note that I don't actively think of people in terms of money, I just think it's an interesting way to distinguish how / why we know or keep up with people, as we are at our very essence, a result of correctly timed consequences (unless you believe in God, which I do, to many people's surprise).


My answer to title of this post used to side with "no" and I'm not entirely sure it's changed. I do think taking a word by word approach is quite important, as "possible," "real friends," and "co-workers" all have to be defined properly and we must agree on such terms to have an opinion either way. You could pause here and instantly think of people you are real friends with right now that you shared a company with and answer "of course it's possible, I've done it." The skeptic in me would encourage you to consider the following array of questions, which from my experience may slightly alter your answer:


  1. Were you ever a direct report to this person?

  2. Were you ever in a competitive position to this person, specifically for a promotion or bonus?

  3. Are both of you still at the same company you met at?

  4. Are you married to this person?

  5. Are both of you over the age of 50, at senior positions at this company, said no all previous questions, and make well over 7 figures at the company and expected to retire at the current organization?

Just food for thought - and plenty of other questions and qualifications that can probably add conditionals to your answer. I'm well aware that this is an unfair exercise, given that even if those questions prompts a thought spiral for you, it doesn't change the fact that you consider this colleague (or ex-colleague) your friend. And we could make the argument that circumstances would apply to any friendship and I could come up with five questions or more for any of my friends supplied with "what if" prefixes that would change my view of friendship with that person. Once again, just food for thought.


I will say, during my time in Investment Banking - where I actually fault the stress, intensity and competition associated with the field (some of the greatest quality human beings I've ever met were during my IB days) - it was hard not to cynically think about being friends with co-workers. In our minds, especially in an overly hierarchy-driven field, colleagues were people that sent devastating emails well after dinner time, called us on weekends to "check how we're doing" in order to assign us more work and discussed more work during happy hour. Especially coming off college, which I projected a much more fantasy land view of friendship, the socialization associated with work saddened me. This hit harder knowing that from now until perhaps a retirement home, the organizations I'd work for would be my main source of community and people, acknowledging that I'd spend more time with my colleagues than my "real family and friends," whatever that meant.


I can spend a little time with the obligatory "in the new normal post-COVID world" perspective in saying that (depending on your role) the real estate that your colleagues will take up in your life can largely be controlled. There's a complete reduction of happy hours (at least you can "drop off" to go attend something quite easily) and a lack of "passing by your cubicle" hello's. If anything, much like our actual friendships post college, it seems like people who want to remain in contact maintain such relationships quite actively, whether it'd be through 1-on-1's or the good old Slack channel. It also very well could lead to employee isolation, the worse case scenario for people actually seeking friends at work, for recent hires or the chronically shy that lack the ability to establish a digital presence. Regardless of one's personality and company dynamics, establishing company friendships, especially if you're fully remote seems rather impossible.


I do think my recent shift to Tech and more specifically start-up culture has shifted my perception on workplace friendships, and this is before I've even begun to go into work in person. As much as it could very well be company koolaid and a cultural "scheme" to get you to enjoy work, the rather flat hierarchy (or lack of), overall young demographic and "campus vibe" does give you the idea that the people you work with could be your friends. It does bring questions of whether or not there's a long term path for you as no one you directly work with seems to be anywhere close to 40 and less hierarchy most likely means less upward mobility. I'm trying my best to not think on these things too much and concentrate on the skillset and intensity that is gained from a tech startup experience (equity is nice too!)


If I were to let go of the cynic inside of me and declare my purest of thoughts, I really want the answer to the post title question to be yes. In this age of the irony associated with hyper-connection correlated with rapid decline of genuine bonds, I often fear the possibility of the disappearance of community. My mom often says that such firm instances of communities are rare, unless you and a group of your friends grew up together, went to college together, and all settled together in successful (or similarly achieving) positions. I'm aware of this reality and also the benefits that I've held from bursting through my comfort bubbles and the blessings associated with moving around.


Whether you're a current co-worker or a future one, don't be afraid to contact me through this website (or you have my Slack!) I'd love to discuss how we could be friends while being paid together.







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