When Work and Friendship Collide
Here’s what experience taught me—sometimes the hard way—about setting boundaries in both life and work.
Last year, I ended a professional relationship with someone I once considered a close friend—at least, I thought we were close. My decision to move in a different direction with my business and stop paying her revealed just how conditional that friendship really was.
She vanished.
She unfollowed me on social media, stopped replying to emails and texts, and ignored public comments in which I celebrated her side hustle or sent encouraging messages.
It was like our 15+ years of friendship had never existed.
At first, I was hurt. But as time passed, I began to see the truth: our connection had been tied to what I could provide—coaching, emotional support, encouragement, and, ultimately, a paycheck. The moment that support stopped, so did the friendship.
That realization stung.
For years, I had poured into her—professionally and personally—cheering her on as she bounced from one role to the next. We used to joke that her strong entrepreneurial spirit made her virtually unemployable. I could relate. That’s why I offered her a role with flexibility and control, which I hoped would tap into her strengths and let her shine.
And for a while, it did.
She contributed some incredible work. But over time, the very patterns I’d helped her navigate in the past reappeared—abrasive communication, passive-aggressive behavior, and growing resistance to feedback. Our working relationship became strained, even though I kept trying to address the issues with transparency and a genuine desire to find common ground.
Eventually, I had to make a tough call.
I paused the working relationship, hoping we could keep the business separate from the personal. I should have known better.
She ghosted me.
Looking back, I don’t regret the decision. I regret ignoring the signs earlier. And most of all, I regret letting the line between friendship and business blur without clearer expectations.
But here’s the thing—I’m better for it.
My team today is phenomenal. I’m energized by the work we’re doing, and more aligned with my purpose than ever before. I’ve learned that hiring a friend out of obligation or empathy rarely ends well. The money, the dynamics, and the unspoken expectations are often too much for a friendship to endure.
Some friendships can survive business. I’m grateful to work with a few fantastic friends with whom mutual respect and healthy boundaries keep everything flowing. But most? Most won’t.
We grow. We evolve.
Sometimes, no matter how long relationships lasted, some aren’t meant to continue into your next chapter, and that’s okay.
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