Generosity is Good Business
Some people are so smart they trip over their own brilliance. They can quote business books, optimize spreadsheets, and calculate ROI down to the decimal point — yet somehow miss the forest, the trees, and the gardener who planted them all.
I recently spent time with someone who fits that description perfectly. They are sharp — a strategic thinker, strong with numbers, good with people (at least on the surface). I genuinely like them. I also find myself shaking my head a lot. They remind me how easy it is to be “penny wise and relationship foolish.”
They run a business in a similar field to the one I used to own, and over time I’ve become something of an informal sounding board. They call every so often with questions — though to be fair, never asking for advice outright… It’s more like talking in riddles that sound suspiciously like requests for help. “What do you think someone might do if…” or “Just curious, how did you used to handle…” I smile because I know exactly what’s happening: pride is wrestling with curiosity.
I was asked if I’d like to go out to lunch. I thought, sure, that’ll be nice — a chance to catch up, talk business, see how things are going. Over sandwiches and iced tea, my brain was picked during the entire meal: staffing challenges, pricing models, client retention ideas. I offered thoughts freely, happy to help. The advice I gave that day could have easily saved thousands of dollars.
Then the check came. And with it, a moment of truth.
I waited for them to pick up the check. There was a moment of awkwardness when it became clear that they weren’t making a move. As I reached into my pocket and withdrew my credit card to add to the folder, they did the same. The silent suggestion was clear: we’d split it. I didn’t say a word, but inside my head a small voice muttered, “Really? After an hour of free consulting, you can’t buy lunch?”
It’s not about the money, of course. It never is. It’s about awareness — or lack of it. I left that lunch realizing the imbalance wasn’t even noticed. They thought we’d had a friendly chat. I thought we’d had a coaching session with sandwiches.
A similar moment popped up — a minor administrative thing that would have made my life — and theirs — slightly easier. Nothing major, nothing expensive. But instead of just saying, “Sure, no problem,” it became a whole discussion about saving a few dollars a month. I was floored. Not because of the cost, but because of the short term mindset behind it.
I wanted to say, “You’re guarding pennies while the dollars — and relationships — are leaking out the side door.”
That experience reminded me of something I’ve seen countless times in business: people who fixate on small costs while ignoring the larger value of connection, loyalty, and goodwill. It’s not just about being cheap. It’s about being short-sighted.
A wise mentor once told me, “Every transaction sends a message.” If you haggle over pennies, you tell people you value money more than relationships. If you pick up the check occasionally, you tell them you appreciate their time. If you nickel-and-dime partners, vendors, or employees, you might save a few bucks this month — but you’ll pay for it later in disengagement, lost trust, or missed opportunities.
Generosity, in business and in life, doesn’t always mean spending money. Sometimes it’s simply being gracious. Saying thank you. Recognizing that someone gave you their attention, their ideas, their energy — and responding with appreciation, not calculation.
When I ran my company, I was always careful with money — but even more careful with people. I understood that saving a few dollars meant nothing if it cost me trust, loyalty, or morale. Treating vendors fairly, recognizing employees, and showing clients confidence and gratitude were never “expenses” in my book — they were investments that paid dividends every single time.
There’s a time for frugality and a time for generosity. The art of business — and of being a decent human — lies in knowing which is which.
The funny thing is, I’ll probably still answer their next call. Because that’s who I am. However, I won’t feel good about providing more help, not like I used to.
It’s amazing how often the smallest gestures reveal the biggest truths. The check at lunch. The tone of an email. The way someone treats a detail that matters to you. Those moments tell you everything about how a person values others.
So if you’re reading this and wondering whether you might be that person — the one guarding pennies while losing people — take a moment to check your math.
Because in the long run, relationships are the only currency that truly appreciates.
