Have you ever had a moment in your life that you immediately regretted? The older I get, the more these moments have a different kind of impact on me.

Last week, I paid for someone’s groceries at the store — and immediately regretted it. Not because they was undeserving, or because I regretted paying it forward, but because sometimes when we think we’re helping, we’re actually making things harder for someone else.

We’ve all been there. The line is building up behind us and our card (or cards) won’t swipe. That exact thing happened to me in the Bahamas when we got off a cruise ship. Silly me — I forgot to tell the bank I was going out of the country. I also forgot to get cash (insert face-palm emoji here).

Lucky for us, the guy at the lemonade stand let us step out of line. I spent an hour on the phone trying to reach someone, only to learn my small-town bank didn’t have weekend customer service (remind me to write another column on why banks suck). Eventually, we got it straightened out and paid for the lemonade. But honestly — wouldn’t it have been nice if the person behind me had just covered the $15?

The truth is, I think that’s why I did it. I’d seen it in a Facebook reel — someone steps up when a card is declined, slides their card in, and everyone cries happy tears. I thought, “Yeah, I’d like to do that for someone one day.” So when I saw it happening to the person in front of me, I didn’t ask. I didn’t pause. I just jumped in and thought I was doing something good.

It wasn’t until afterward, when you handed me a $100 bill I couldn’t refuse, that I realized: you were probably from out of the country. Your cards weren’t working, and you really needed that cash. On top of that, I might have embarrassed you in an already stressful moment.

Here’s the thing: social media makes “kindness” look like a reel. But kindness isn’t supposed to be about us. It’s supposed to be about them. Real kindness requires paying attention, asking, and respecting someone’s dignity — not just copying a TikTok trend and hoping for a feel-good moment.

I’m not mad at myself. I just learned a hard lesson. And I’m hoping to pay this one forward to all of you.

Jen Bailey

Hi! I’m Jennifer Bailey and I partner with entrepreneurs who have massive ideas that could change the world. Most marketing is meaningless. Filled with empty promises, its only job is to bring in new traffic, new leads, and new customers. But I’ve drawn a line in the sand, and I’ve learned that marketing can do so much more than reach business goals and build profit. My methods give businesses the fire and soul they need to reach the right people, set the groundwork for sustainable relationships, and offer true value to the people on both the giving and receiving ends of marketing.

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