My close friend is now my direct manager. We used to party together, but now she's decides if I deserve a raise.
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- In my early 20s, I landed a job that became more about partying than working.
- I became close friends with my coworkers, and we all spent weekends together.
- Now, I work for one of those friends, and our dynamic is difficult to manage.
When I first graduated from college, I landed a sales job in New York City. The friends I met there in the first few months were some of the closest I had ever had in my life.
Nothing brings you together like late-night work sessions and huge commission checks you spend on anything you want because you're 22 and have never heard of a high-yield savings account.
Making work friends in my early 20s gave me the college experience I never had. We often had weekday sleepovers, where we would roll into the office in the same clothes we wore the day before. The idea of professional boundaries never even crossed my mind.
That's until my close friend at that job recently became my direct manager.
I got a new job at a tech startup and learned about professionalism
When I started working at a tech startup, I spent the next seven years forming close relationships with my co-workers, direct reports, and even my boss.
I was introduced to the delicate balance you can create between a boss and a direct report that allows you to be completely yourself while also maintaining mutual respect and a sense of authority.
We could seamlessly jump between presentation prep and sharing personal anecdotes about our struggles, our goals, and everything in between. The dynamics were playful and professional, whereas my first job was all play and no work.
As it usually goes, after seven years at the tech startup, I decided to part ways with the business. Unemployed, I found myself at a wedding next to an old friend and coworker from my first play-only job. She had recently gotten recruited to take over the office and offered me the opportunity to come on board as a contractor for a few months to earn some extra cash while I was in between jobs.
A few months turned into a full-time position
After everything I learned about this delicate balance of coworker and friend, nothing could have prepared me for that reporting line shift. The last time I worked with my now boss, we were 23 years old, night swimming on Fire Island at three in the morning on a Thursday. Now, I'm filling out my end-of-year review, reflecting on how I did so that my friend can decide whether or not to give me a raise.
To put it simply, it felt pretty weird.
I have always thought of her as a wild friend first and a coworker second, but since rejoining the company, we have both had to flip that prioritization. It helps that we're almost 10 years older, but it's still been a hard transition.
We have had to put our friendship on the back burner and be more professional with one another. We use Teams to catch up instead of texting. We share weekend plans during our 1:1 instead of naturally calling each other to check-in. I find myself more hesitant to say things that I wouldn't have given a second thought to before, and I can feel her hesitation as well.
In some ways, it feels like I am mourning the loss of our pure friendship, which is now muddled by salary discussions and time off requests.
As hard as it is, there are also a lot of benefits to reporting to a friend
Maybe it's a loss of a pure friendship, but it also feels like a gain of something pretty incredible.
I have always felt that the most important thing about a work environment is who you work with. I feel safer and more comfortable knowing that I have a friend in my corner, and I think she feels the same way, too.
I never would have even known about this job opportunity without my friend encouraging me to take the role. Even more importantly, she knows me so well that she has faith in my abilities and trusts me completely. I have been given more responsibility and autonomy in a few months than most people get after years because it takes time to build that level of trust with a new manager.
Working for a friend works for me — for now
Right now, in my career, I crave autonomy and trust. I believe I have earned that faster by working for a friend.
There may come a time when I'm seeking more mentorship or diverse experience from my manager. When that time comes, I will need to shift away from reporting to a friend and start fresh.
When I consider the times I have worked with friends vs. when I have not, working with them comes out on top every time. But working for them might be something I only do a few times in my career.
