Navigating the Challenges of Working for a Close Friend

New York City: So, I started this job a while back, and it was all about fun and hanging out with coworkers. We were like a little family, partying more than working. Fast forward, and now one of those friends is my boss. Talk about a tricky situation!

When I graduated, I got a sales gig in NYC. The friends I made there were some of the best. Late nights and big paychecks made it feel like college all over again. We even had sleepovers during the week, showing up to work in the same clothes. Professional boundaries? Never heard of them!

But then, my friend from that job became my direct manager. I thought I knew how to balance friendship and work, but this was a whole new ball game. We used to have fun together, and now I’m filling out performance reviews for her. It’s just weird.

We’ve had to change how we interact. Instead of casual texts, we’re using Teams for work chats. I find myself holding back on things I’d usually say without a second thought. It’s like I’m losing that carefree friendship vibe, and it’s tough.

Still, there are perks to this situation. Having a friend as a boss makes me feel secure. She knows my strengths and trusts me, which has led to more responsibility than I’d usually get. I wouldn’t have even known about this job without her nudging me to apply.

Right now, I really value the trust and freedom I have. But I know that if I want more mentorship or different experiences, I might need to rethink this friend-boss relationship. Overall, working with friends has been great, but working for them? That might be a rare thing for me in the future.