Lessons in Generosity

A glass jar of coins and notes on a table

~by Haley Lynn Gray~

Every year, we took turns standing outside with our daughters, selling Girl Scout Cookies. The girls learned a great many lessons at those booths. One of the biggest was about generosity.

Over and over, they discovered that the people who seemed to have the least to give were often the most generous.

What we saw

So many times, someone would stop, ask about the cookies, and then go and get cash — from their car, from a cash machine, from the bottom of a bag. You could tell it was a stretch for them.

And they were so generous. They’d buy a box, and then leave a donation on top. A teenager would drop five dollars in the jar and walk away with nothing. People who clearly didn’t have much to spare would give anyway, and seem glad to.

It happened often enough that my girls came to expect it — and it changed how they thought about generosity.

It isn’t just our experience

Researchers have found the same thing. In a 2010 study, psychologists at the University of California, Berkeley and the University of Toronto — including Paul Piff and Dacher Keltner — found that people with fewer resources were, on average, more generous and more helpful to others than people with more.

Their explanation is thought-provoking. People with less often depend more on each other, so they tend to be more attuned to other people’s needs. Having more can make it easier to feel you don’t need anyone.

It’s a reminder not to judge anyone’s generosity by what they seem to have.

What it means for leaders

This stayed with me, because it applies well beyond a cookie booth.

Generosity isn’t about how much you have. Plenty of leaders wait until they’re “successful enough” to help others. The people at our booth didn’t wait. They gave what they could, when they could.

Small acts matter enormously. Five dollars from a stranger meant a great deal to a little girl standing in the cold. A few minutes of your time, an introduction, a word of encouragement — these cost little and can mean a lot.

Don’t assume who will help. Our assumptions about people are frequently wrong. The support you need may come from the least expected place.

Remember where you started. Research suggests power and plenty can make people less attentive to others. The more successful you become, the more deliberately you have to stay generous.

What my daughters took away

They learned to ask everyone, and to be grateful to everyone. They learned that kindness often comes from people who are struggling themselves. And they learned that being generous doesn’t require being rich.

Those are lessons I’m glad they learned early. I’m still learning them myself.

More on what Girl Scouts taught me about leadership.

If this resonates, you don’t have to figure it out alone.
We host small, thoughtful Round Table conversations inside Women’s Entrepreneur Network where women leaders talk through exactly this kind of challenge.
You’re welcome to join us.

Related Posts

How to Write Your Vision and Mission for Success in Your Business

How to Write Your Vision and Mission for Success in Your Business

Most mission statements are useless, and there's a quick way to prove it. Take yours, or one you admire. Swap in a competitor's name. Does it still work? If it does — and it almost always does — the statement isn't describing your business. It's describing...

You Don’t Need More Courses — You Need Better Conversations

You Don’t Need More Courses — You Need Better Conversations

There is a particular kind of business owner I meet constantly. She has bought the courses. She has the frameworks, the templates, the recorded masterclasses she fully intends to finish. She can explain her own problem more articulately than most consultants could....

Why Good Conversations Beat Good Advice

Why Good Conversations Beat Good Advice

Ask ten experienced business owners what you should do, and you will get ten confident, contradictory answers. All of them will be sincere. Most of them will be useless. This isn't because those people are wrong. It's because advice and conversation are different...

Who Is Actually Useful to Think With

Who Is Actually Useful to Think With

The phrase "talk it through with someone smart" is almost right, and the part it gets wrong causes real problems. Intelligence is not what makes a person useful to think with. Some of the sharpest people I know are actively unhelpful when I'm stuck — and a few...

What to Do When You’re Stuck in Analysis Paralysis

What to Do When You’re Stuck in Analysis Paralysis

Analysis paralysis is rarely an information problem. People stuck on a decision usually have plenty of information — frequently more than they need. What they don't have is a rule for when to stop looking. The idea that fixes this Herbert Simon, who won the...

Decision Fatigue: What’s Real and What Isn’t

Decision Fatigue: What’s Real and What Isn’t

By four in the afternoon, decisions you'd have made carefully at nine get made carelessly, or not at all. Most people who run something recognise this immediately. The usual explanation for it is wrong, or at least much shakier than it's presented. Which matters,...

Find what you need

Lead Your Team

Delegation, hiring, difficult conversations, and becoming the boss you'd want to work for.

Build the Business

Pricing, launching, systems, and building something that doesn't depend on you.

Women in Leadership

Negotiation, the pay gap, and what the research actually says about women who lead.

Get Seen

Being visible without the cringe — podcasts, content, and being remembered.

Lead Yourself

Courage, your inner critic, time, and protecting what matters most.

You're Not Alone

The loneliness of leading, and why the best owners don't solve everything alone.