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What If a Boss and an Employee Swapped Roles? We Tried It. It's a little something we like to call the "boomerang boss."

This story appears in the January 2023 issue of Entrepreneur. Subscribe »

Image Credit: Zohar Lazar

The Current Boss: Megan Flood, 36

After college, I took an internship at a PR and marketing firm called Maloney & Fox. Margie was one of the firm's cofounders and my boss. I loved her motto: "Let me be the wind beneath your wings. Tell me what you want to do here, and if it also helps the company — let's make it happen."

So I told her. I had a lot of drive and ambition to create an art department at the agency, and she met every request with a yes. We quickly trusted each other, and I learned a lot: how to avoid micromanaging, how to build a culture, how to "just pick up the phone," how to sweat the right stuff.

Three years later, I left to start my own firm, Marine Lane. Margie eventually sold hers, then held big jobs like U.S. creative director of the consumer PR practice at Ogilvy. We stayed in touch. Eventually she was looking for a new pace of life, so I asked if she'd come work for me. How else could I score someone as experienced as her? I was thrilled when she said yes, and laughed when she picked her own title: consigliere.

People ask us if the transition was hard. Honestly, it wasn't. Margie never "bossed" me around, so I know better than to "boss" her (or anyone else on our team). She knows instinctively that the last word must be mine and respects that. But also, like anyone with great boss instincts, she pushes me to be a more forthright leader. She knows that I'm less confrontational than maybe I should be, and Margie is proactive whenever she sees an issue — which she openly credits to 27 years in therapy. Together, we can cut it off at the pass.

The best working relationships go beyond hard boundaries; they're about the small ways you give and take. That's what we have. I don't pay her anything close to what she'd get working full time elsewhere, for example, and in turn I accommodate her slightly erratic schedule. And I'm forever grateful for the value she provides. Her Rolodex (which is what she insists on calling it!) is stuffed with contacts, and she's a fount of new business leads and myriad talents. Also, I look younger than I am — and I know that many times, a client has been happy to have someone older and likely wiser in the room.

As far as I'm concerned, hiring Margie is the deal of a lifetime for me. We both know that this arrangement will not be for everybody. But for everybody it might be good for, I think we'd both say: Go for it with gusto!

Related: How to Build Meaningful Relationships in the Workplace

The Former Boss: Margie Fox, 60

I have the best job ever, and the best boss ever. And that is saying a lot, because I thought I was the best boss!

I am the oldest by multiple decades at our office, and still the least mature. Somewhere along the line, that has become a winning combination. I take work very seriously — just not myself. What I bring to the table is 35-plus years of experience and the knowledge that while most of that experience is relevant, some no longer applies. I help the younger staff understand that people of different ages and stages in life take in information differently (including that, yes, I still read The New York Times in print).

As I neared 60, I started to think about what's most important to me now. Money is, fortunately, not on the list: I am lucky to have earned enough in my prior iteration that I no longer need to chase huge dollars to support my lifestyle. Health benefits, however, are still important (which is one of those things you never think about when you're younger).

Work is also still important to me, but not quite in the same way as before. I no longer want the responsibilities and pressures associated with running a company. I've already done all that. I also don't want to work 40 hours a week in an office anymore. Now I can watch Megan do all of this — managing staff, billing, HR, insurance, and all that jazz — and appreciate exactly how herculean of a task it is.

By working with Megan, I can work the way I like. I am a crazy early riser, so I can get tons done between 5 a.m. and 8 a.m. I also want to travel more, and now have the latitude to do so — but I only go at a time that works for her. Sure, the job sometimes interrupts these adventures. But I can also dial in from wherever I am. An occasional Zoom during time off is a very small price to pay for this freedom.

Finally, growth is still very important to me. I grow daily by being in the company of younger, über-talented, kind people. But especially Megan. She is a unicorn of a human and I believe in my heart of hearts that what we both get out of this relationship is way more than the sum of two parts.

I want to work like this forever. It is beyond enlivening. I was at a 60th birthday party for a best friend in Arizona recently, and the group was fascinated by (and a little envious of) my work-life balance. I tried not to gloat, but I truly encouraged them to seek out similar gigs. It is true, though: I was the worst pickleball player in the group.

Related: 4 Limiting Beliefs That Harm Workplace Relationships

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