Why being easy to be around is so expensive
A close friend owed me money. Under $200. Not insignificant — I had organized and facilitated an outing, and while we had settled the larger amount, when I checked out of our hotel, there were extra charges, but not enough to cause any real financial strain. She’d acknowledged it when I first mentioned it. Warm, gracious — of course, so sorry, I’ll get that to you! And then silence.
Weeks passed. And instead of simply following up, I did what people-pleasers do best: I built her a very elaborate defense.
She’s been so busy.
She’s switched banks — Venmo can be glitchy with that.
To her, $200 might just feel like a rounding error. I don’t want her to think I’m petty.
Our friendship is worth so much more than this.
Every story was generous. Every story was reasonable. And every story kept me OUT of integrity with myself when all it would have taken was sending a two-sentence text. I want to pause here and tell you something: I coach people on this. I wrote a book about moving from armor to authenticity. I talk about people-pleasing patterns for a living. And I still did this.
If you’ve ever rolled your eyes at the idea that “doing the work” means you somehow graduate from these patterns — I’m here to tell you, with full humility, that you don’t. You simply get better at catching yourself. Eventually.
Finally, after weeks of this internal legal briefing, I mentioned it to my husband, Bill. He looked at me. “What? Why haven’t you just reminded her? This is NOT a big deal.” And then, the detail that landed like a small grenade: “Her husband is the first one to tell me when I owe him money. He doesn’t think twice about it.”
I sat with that for a moment. UGH, I had been tying myself in knots to protect her comfort — manufacturing reasons why she might have forgotten, why she might not be able to pay, why bringing it up might embarrass her — while her husband, on the other side of this very friendship, operated with zero hesitation. He just asked. No stories. No six-week runway. No workshopping the emoji.
That’s the thing about people-pleasing that we rarely name directly: it is NEVER about the other person. We tell ourselves we’re being considerate, patient, generous. But what we’re really doing is avoiding the discomfort of being seen as someone with needs. Someone who tracks things. Someone who — God forbid — expects to be paid back.
I had convinced myself that her potential discomfort was more important than my legitimate expectation. That my role in making the whole outing happen didn’t quite earn me the right to a simple follow-up.
That’s not kindness. That’s self-erasure with a generous coat of paint.
I say this as someone who is still — still — learning to put the paintbrush down.
Feeling like a woman who was definitely NOT practicing what she was preaching, I promptly sent the reminder. Two sentences. My friend paid within minutes; of course, she did. “Thanks for the reminder!” she texted back. No awkwardness. No offense. No damage to the friendship. Just: thanks for the reminder. Six weeks of stories. Two sentences. Minutes.
If you’re reading this and thinking, oh, I do this too — I’m not surprised, and you’re not broken. This is one of the most common and quietly costly patterns I see in the women I work with, and in myself. The second-guessing. The elaborate justifications. The protection of everyone’s comfort except your own. We’re in it together.
Here’s what I want you to sit with:
Where are you building a case for someone else’s inaction — at the expense of your own?
What story are you telling yourself about why you haven’t asked, followed up, or simply said: hey, I think you forgot?
Because the stories we construct to protect other people from mild discomfort usually end up costing us far more than the thing we were afraid to ask for. The $193 came back in minutes.
The six weeks I spent talking myself out of asking? Those I don’t get back.
Hit send. You’ve earned it.
💛 Andrea
P.S. If this one landed, forward it to a friend who needs the nudge — the one who’s been sitting on a text they’re completely entitled to send.
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I'm Andrea Mein DeWitt—author, Professional Certified Coach, and self-proclaimed warrior in recovery. After 32 years in education, I transformed my career in my early 50s and now help high achievers stop forcing their way through life and start living it. I write from the San Francisco Bay Area, where I live with my husband Bill, our yellow lab Maggie, and a perfectionist inner critic I've learned to befriend (mostly)."
My book Name, Claim & Reframe: Your Path to a Well-Lived Life was featured on NBC's TODAY Show as 2023's best motivational read. The audiobook just dropped on Audible, because transformation shouldn't require sitting still.
