- In my early 20s, I found a job that became more about partying than work.
- I became close friends with my colleagues and we all spent weekends together.
- Now, I work for one of those friends and our dynamic is hard to manage.
When I first graduated from college, I got a sales job in New York City. The friends I met there in the first few months were some of the closest I’d ever had in my life.
Nothing brings you together like late-night work sessions and big commission checks that you spend on whatever 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 would often sleep in on weekdays, where we would enter the office in the same clothes we had worn the day before. The idea of professional boundaries never even crossed my mind.
That is 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 building close relationships with my peers, direct reports, and even my boss.
I was introduced to the delicate balance you can strike between a boss and a direct report that allows you to be fully yourself while also maintaining mutual respect and a sense of authority.
We could seamlessly transition between preparing the presentation and sharing personal anecdotes about our struggles, our goals, and everything in between. The dynamic was playful and professional, whereas my first job was all play and no work.
As is usually the case, 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 colleague from my first job just for play. She had recently been 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 money while I was between jobs.
A few months turned into a full-time position
After all I learned about this delicate balance of colleague and friend, nothing could have prepared me for that change in reporting line. The last time I worked with my now boss, we were 23, night swimming at Fire Island at three in the morning on a Thursday. Now, I’m completing my year-end review, reflecting on how I acted so that my friend can decide whether or not to give me a raise.
Simply put, it felt quite strange.
I’ve always thought of her as a wild friend first and a co-worker, but since rejoining the company, we’ve both had to shift that priority. It helps that we’re almost 10 years older, but it’s still been a tough transition.
We have had to put our friendship on the back burner and be more professional with each other. We use Teams to catch up rather than send messages. We share weekend plans during 1:1 instead of naturally calling each other to check in. I find myself more hesitant to say things I wouldn’t have thought of before, and I sense her hesitation as well.
In a way, I feel like I’m mourning the loss of our pure friendship, now clouded by salary discussions and time off requests.
As difficult as it may be, there are also many 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’ve always felt that the most important thing in a work environment is who you work with. I feel safer and more comfortable knowing I have a friend in my corner and I think she feels the same way.
I would never have 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 confidence in my abilities and trusts me completely. I’ve been given more responsibility and autonomy in a few months than most people get in 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 want autonomy and confidence. I believe I acquired this most quickly by working for a friend.
There may come a time when I’m looking for more mentoring or different experience from my manager. When that time comes, I’ll have to quit reporting to a friend and start over.
When I consider the times I’ve worked with friends and when I haven’t, working with them comes out on top every time. But working ABOUT they may be something I only do a few times in my career.
