22 Lessons from Half a Lifetime of Growing Generosity

Would you indulge me in a personal one today?

Two days from now – June 7 – marks 22 years since I walked into my first day in the nonprofit sector.

I was 22 years old. Fresh out of college, a project manager at a marketing agency called Masterworks, and I was assigned to my first clients – charities like Union Rescue Mission, Holt International Children’s Services, and Gospel Communications International. I was floored that it was possible to have a career working with nonprofits to help them accomplish their missions using marketing and fundraising. 

I didn’t know it then, but the people I’d meet and the work I’d get to do over the next 22 years would shape the rest of my life.

I’m 44 now, which means that as of this Sunday, I will have spent half of my life working in and around this sector. Helping nonprofits raise money, sure. But more than that, helping leaders and organizations inspire generosity more broadly, and helping them see a future that is possible, but does not yet exist.

Over the past two-plus decades, I’ve picked up some life lessons, so today, I thought I would share some of those with you.

Some Things I Have Learned

A quick word about what these lessons are – and aren't.

When I sat down to write these out, I expected to land on a list of fundraising principles and tactics. Lessons about offers, channels, strategies, sustainer programs – the things I write and speak about week in and week out.

But that's not what came out.

What came out instead was a list about people. About leadership. About how to work, how to learn, how to make decisions, and how to treat the colleagues, clients, mentors, and donors you get to walk alongside. 

The more I thought about it, the more the list made sense. The fundraising tactics are in the book, the podcast, and 195 prior Wave Reports (yes, this is Wave Report #196). 

Those fundraising insights will keep coming, but the real lessons from 22 years — the ones I'd tell my 22-year-old self if I could — aren't really about fundraising at all. They're about the human relationships underneath it. 

Because growing generosity, it turns out, has always been a people-centered endeavor.

Some lessons I learned the hard way, like when I mixed up the name of our client's CEO's wife and mailed a letter to tens of thousands of donors with the wrong name. 🤦 (I learned: Details matter, and are worth double-checking!)

Or when I wrote a frustrated email about another leader to my boss, only to send it TO that leader by accident. 🤦 (I learned: Write your praise, but speak your criticism.)

Other lessons I learned from the leaders, mentors, and colleagues I've had the privilege of working alongside. Lessons that have shaped not just how I do the work, but why I'm as motivated as ever to do everything I can to help inspire generosity.

So, taking the advice I’ve written about from The Power of Moments — to mark significant milestones — today, let's look at 22 lessons from half a lifetime of growing generosity.

My hope is that whether you're 22 years into your own journey or just getting started, you'll find something here worth carrying with you.

22 Lessons from 22 Years of Growing Generosity

1. Generosity is about more than money, or time, or talent. Generosity is too often conflated with “giving money.” Further, I think generosity is unnecessarily confined to the giving of “time, talent, and treasure.” I’ve been the recipient of generosity in other ways – others have been generous with their connections, wisdom, and their trust. All of these are acts of generous people, and I hope I've inspired others to be generous in ways that go far beyond money.

2. Generosity begets generosity. Acts of generosity lead to acts of generosity. This applies to fundraising and to life. Have you ever been the recipient of another’s generosity? How can you be generous with others today? 

3. Remember people’s names. When you take the time to remember another person’s name – a simple thing – you show them that they matter. We all want to be known. It feels good, and using another person’s name is a small way to say you see them and they matter. 

4. Smile when you see people. This might seem like an odd one, but stick with me… Think of a time when someone’s face lit up to see you – an old friend, a colleague, someone at your place of worship, or around town. There isn’t a much better feeling than when someone is happy to see us. Give that gift to others by being happy to see them, and letting them know it!

5. Bring the best out of those you work with. Whether colleagues, clients, or contractors, look for each person’s unique strengths. Compliment those strengths, and draw on them. Treat everyone like a valued teammate and collaborator. 

6. Don’t hire people who are just like you. When I was younger, I overemphasized my own strengths and, subconsciously, I think I gave people with similar strengths more credit. I eventually learned to hire people who complemented my strengths with strengths of their own, which means they probably aren’t like me at all! Shared values are important, but look for diverse gifts.

7. You need others. Every strength has a corresponding weakness, and no one can succeed in a vacuum. We are all influenced by the people around us. Many different gifts are needed to accomplish anything significant, so the better you understand yourself and appreciate the gifts of others, the more wisdom you will have to see that you need them and tap into those gifts. 

8. Take notes. Some of the wisest and most generous people I know constantly take notes. I think of people like Jerry White, president emeritus of The Navigators and author/co-author of 16 books, who carries a notebook and will regularly bring it out during a conversation. I started doing the same about a decade ago. I have dozens of notebooks. I don’t always look back at them, but taking notes helps me remember little details, stay present, and show the person I’m with that I care about what they have to say. 

9. Maintain a learning posture. Two things are true as I’ve gotten older – first, I’ve learned more, and second, the more I’ve learned, the more I realize what I don’t know. While it can be tempting to declare yourself an expert and let your thinking harden around what you already know, fight that urge. The deeper you go down the rabbit hole, the more you realize you always have to be learning.

10. Don’t mistake activity for progress. I learned this from Steve Woodworth, CEO of Masterworks and my boss and mentor for many years. Just because you are busy doesn’t mean you are making progress towards what matters. (Also… have you actually defined what matters?)

11. People are motivated differently, but we all need something to move towards. Bobb Biehl taught me that leaders are motivated by different things. Some leaders are motivated by goals, others by opportunities, while others are motivated by solving problems. Most days, I’m a goal-oriented leader – set a goal, and I’m motivated to reach or beat it. Other people are problem-oriented – they see problems that need fixing. Still others are opportunity-oriented – they see opportunities to seize. The beauty of this knowledge is that any vision can be described in any of the three ways: a goal to be achieved, a problem to be solved, or an opportunity to be seized. What motivates you? What motivates those leaders around you?

12. Set boundaries for what you will and won’t do. Travel, for instance – I was fortunate enough early in my marriage to have a boss (Steve, mentioned above) who told me, “Talk to Heather and decide what an acceptable level of travel is for your marriage, and we’ll stick to that.” We decided on twice a month, and I’ve stuck to that boundary for nearly two decades now.

13. Schedule experiences, and learn to anticipate them. On a practical level, as life goes on, you will tend to get busier. It becomes imperative, then, to book out and hold time to recharge and get into different environments. Being married to a teacher and having school-aged children means every spring break, Christmas break, and summer break are our time to invest in experiences. We’ve typically got a loose plan of things we’d like to do a few years out, and settle on things about one year out. And, once you have experiences planned, learn to anticipate them. Talk about them, dream about them, get your kids talking about them. I learned this from my wife Heather’s family – they plan and anticipate experiences well. I joke that when we have a trip coming up, by the time we get in the car or on the plane, we have gotten our money’s worth. We get so much value from the anticipation that comes from planning and dreaming about the experience.

14. Respect and appreciate others’ expertise. There is a psychological phenomenon – the Dunning-Kruger effect – that shows that when we know a little bit about a subject, we tend to overestimate what we really know. But the deeper we get into any specific area, the more we realize how far the rabbit hole goes (see #9 above). It’s just smart, then, to assume that another person’s “rabbit hole” of expertise must be as deep as yours. Don’t take others’ expertise for granted any more than you would want people to take your expertise for granted. 

15. Burn boats (sometimes), not bridges. I’ve learned from wise friends over the years never to burn a bridge. Relationships are what matter in the long term. But I’ve also learned that sometimes, it’s important to burn the boats – to make it so there is no way back – only forward. 

When I started what has now become The Center for Sustainable Giving, I felt I had to burn the boat by leaving my prior executive role at the agency. I could have tried to transition slowly and build the new opportunity, which felt safer, but I knew myself and chose to go all in on the new thing. For me, knowing it “had” to work was very compelling. I knew I needed to burn the proverbial boat if this was going to have a true chance at working.

16. People become how you treat them. We have much more influence on who others become to us than we realize. If you treat others as competitors, they will likely become more competitive. If you treat others as friends, they will more likely reciprocate and become friends. If you treat others with distrust, they will treat you with distrust. Be wise, of course, but consider that how you treat others might just shape who they are to you as much as who they are in the first place.

17. Learn how to move from data to strategy. One of the things I’ve noticed about the most effective leaders is that they have a pulse on what is going on – they know the data – and that helps them figure out what to do about it. I’m constantly on a quest to understand what is happening and what I should do about it. The same goes for the organizations we work with to help grow sustainable giving.

18. Find what’s working, and do more of that. I learned this lesson from Rory Starks, with whom I worked for 18 years. Rory had helped build organizations like World Vision and Food for the Hungry before joining the agency. He had a great track record of growing things, and I asked him one day how he did it. He said, “Dave, it’s pretty simple – I figure out what’s working, and I do more of that.” That’s a simple but powerful principle that speaks to a core insight – leaders tend not to maximize what's working. What if you find the bright spots - those things that are working at least a little bit, and what if you could do 2X, 5X, 10X, 100X of that same thing?

19. Leverage your natural resources. Every organization, every individual has what I call “natural resources” – things you have that others don’t. Things that you might take for granted, but when you recognize them and tap into them, can create tremendous results. Rather than worrying about what they don’t have, the best leaders I’ve known have a sense of what those natural resources are, and they tap into them. 

20. Act with courage and take calculated risks. I don’t love change, I don’t love risk, and I love to overthink things. This might come as a surprise to readers who know I love to start things and am constantly thinking about innovation and how to take advantage of new trends and opportunities.

One of the muscles I’ve had to develop over time is making decisions and taking calculated risks. Many times when a decision feels risky, it’s not truly a risk – the downside is not catastrophic. As my colleague Rory (#18 above) would say to me, “Dave, make a decision, and then make it right.” What’s important is to act, to make decisions. You can always adjust later to make it right, but not if you don’t make a decision now. 

21. One move at a time (keep opening doors). Related to the above on making decisions and taking calculated risks, I used to liken life to a game of chess. If I could, I would plan six moves ahead at all times. If I do this, what will that lead to, and what will be the options after that, and after that? Then two things happened – first, I realized I can’t plan that many moves ahead, so I focused on what’s the next move or two. Second, I realized that sometimes doors don’t open unless you walk through the prior door. 

I think of life now more like a series of doors – and I just keep opening doors that seem to be the right ones. Some will be dead ends, but others will lead to more doors, and that’s exciting.

22. The job of any leader is to manage the present while inventing the future. I learned this years ago from an interview with an incoming CEO of the Coca-Cola Company. When asked what the biggest challenge she faced as a leader was, she said something that I’ve never forgotten. She said that her biggest challenge is the same as that of any other leader in her position – managing the present while inventing the future. I’ve never forgotten that. 

Our job as leaders – my job and your job – is to manage the present while inventing the future. We can’t do just one or the other – we must pay attention to today, while at the same time thinking about tomorrow. That isn’t good leadership – that’s just leadership.

Twenty-two lessons. Twenty-two years. Half a lifetime in.

Reading back through them, the pattern became clear to me — almost none of them are really about fundraising. They're about people. The mentors who shaped me, the leaders who trusted me, the donors who taught me what generosity actually looks like, and the colleagues and clients I've gotten to build alongside. I'm grateful for every one of them.

And I'm more energized than ever about the next 22. 🌊

💡 Takeaway: Growing generosity is, at its core, a people business. The most important lessons I've learned over 22 years aren't really about fundraising – they're about how to treat people, how to keep learning from them, and how to invite them into work that matters. Wherever you are on your own journey, that's where I'd start.

Until next week… Surf’s Up! 🌊

  - Dave