The #1 Rule to Working With Friends

Get a contract because people can get funny about money.

Felicia C. Sullivan
Falling Into Freelancing
8 min readNov 29, 2019

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Licensed from Adobe Stock // Jacob Lund

I lost a friend this year. Let’s call her Meg. I first met Meg a decade ago when I sat across from her in a conference room while she fired questions at me. And she wanted the goods because in two week’s time she would be reporting to me. I remember it being warm for November, so I took off my jacket while she spoke. She paused, mid-question, to compliment my sweater. I laughed and told her I liked soft things. Cashmere, shearling, cotton, the bellies of kittens. I watched her tense shoulders ease.

For the remaining twenty minutes, I told Meg about the kind of boss I wanted to be. How I’d consider her a partner rather than a direct report because a title doesn’t grant you respect — you gain it by giving it. You earn trust when you’ve proven that you’re trustworthy.

Meg was one of the smartest women I’d ever met. But she was also fragile and insecure; I never understood why she was always so hard on herself. Always hawking what she ate. Always obsessing over client presentations and marketing plans. Sending emails in the middle of the night. During her annual review, she presented a 20-slide Keynote defending her request for a raise. Her presentation was funny and self-deprecating, but she didn’t need it. How was it that she couldn’t…

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