When I first moved to New York City, I worked in book publishing, where I assisted two lovely women (Michelle and Jen, hi!). As clichéd as it sounds, we became like a little family during my year at the company. Once, they took turns cradling me in their arms when I showed up violently hungover to our office Christmas party. (I was 22, and it was the holiday season—what can I say?) Our weekly check-ins became like mini therapy sessions. We even exchanged framed photos from The First Wives Club, our favorite movie, with our faces photoshopped over those of Bette Midler, Goldie Hawn, and Diane Keaton.
When I realized I was ready to move on from that job to pursue my dream of writing here at Glamour, I was a wreck about how to tell them—and petrified that leaving would break our bond. Before I quit, I spent a lot of time thinking about their communication styles and how I could make them feel valued. Gifts and notes were a big part of our relationships, so after I delivered the news face-to-face, I gave each of them a card. I peppered my note with anecdotes about the great times we’d had together, inside jokes, and how their mentorship had prepared me to take on my next role. Now they’re still my biggest cheerleaders. We have dinner at least every other month, they read all of my articles, and I stay just as caught up about their lives. It’s not always easy to let your boss know you’re ready to move on, but the very best ones will still be proud of you, as sad as they are to see you go.
We spoke to former employers and employees who still get happy hour drinks, share memes over DM, and go to one another for advice about how they were able to leave the nest, while still keeping their relationship intact.
Give Your Boss Their Due
“Before I became the editor-in-chief of Glamour, I was the head of social media and director of strategy at CNN. My boss was Meredith Artley, CNN’s editor-in-chief. We worked together for about three and a half years, and I don’t think I could be in this job right now if she hadn’t been my previous boss. When this opportunity at Glamour came up, I was actually really happy in my job—so it was surprising that I was leaving.
“When it came time to tell Meredith I was resigning, she was very excited for me. We both shed some tears, and we were mutually very excited as well as mutually upset that we were no longer going to be working together. But she saw it as a big move for me, because the best bosses are your biggest cheerleaders when you’re with them and when you go onto different, bigger, and better things. It was also really important to me to make sure Meredith knew I wouldn’t be getting this job without her. Don’t be shy about articulating how much this boss meant to you. If you’re leaving because your boss has helped you grow into a place where you can take this next job—like mine did—make sure you say that.
“If you want to remain friends with your boss, make sure it’s not just platitudes when you say you want to stay in touch. I reach out to Meredith all the time. I’m always chasing her for dinner and drinks, so don’t just say it—actually follow up. In my first few months at Glamour, I even went to Meredith for advice about some of the things I wanted to tackle in my new role. Make sure to keep them in your corner.” —Samantha Barry, editor-in-chief of Glamour
Be Real With Them
“I was a project manager at an agency in New Orleans for six months. I worked under the COO, and we were close. She was a great mentor, and I spent most of my days in her office working through problems. When I knew I wanted to leave, I had a conversation with her very early about what I was thinking about for my next step, and was honest that I was toying around with a few ideas. Although she didn’t want me to leave, she was able to give me great advice about following through on what’s best for me. She knew that I needed to spread my wings further and didn’t hold back on encouraging me to leave if I needed to. When I finally put in my resignation, she already knew it was coming. The conversation was mainly filled with advice and encouragement.
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