My old boss in Tampa told me to never mix money with friends. She was dead wrong about one part.

Val Webb · 2026-09-23T20:55:04.865197+00:00

When I started dog walking on the side, my old boss Pam told me to never accept payment from close friends because it always ends badly. I ignored her and charged my buddy Derek $15 a walk for his corgi for 6 weeks, and he paid me every single Friday without me asking once. Then he started telling other people in our group, and now I have 4 regular clients who are all friends and not one has stiffed me. Pam's rule made sense for big stuff like renting to a friend, but for small weekly cash jobs it has been the opposite of true for me. Has anyone else found that a small paid favor actually made a friendship stronger instead of weird?

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My old boss in Tampa told me to never mix money with friends. She was dead wrong about one part. | Adult Friendship Rules - Rigidtalk