The Intersection of Gratitude and Generosity

Today’s Wave Report will be a reflective one – I hope it provides some perspective. 

I believe that gratitude and generosity form a virtuous cycle. Each leads to the other, and they reinforce one another.

When I practice generosity, that leads to gratitude.

When I practice gratitude, that in turn leads to generosity. 

Six Insights at the Intersection of Gratitude and Generosity

Several things come to mind as I reflect on the interplay between gratitude and generosity. 

1. Generosity puts my relationship to possessions in perspective. When I give, it loosens my grip on what I think I own. It reminds me that I don’t ultimately “own” anything in the final sense. That I am not a consumer first and foremost. It helps me to identify as a giver. 

2. Generosity makes me feel good. My parents taught me the importance of being generous early on – with my time, talent, and treasure. When I give, it feels good. The joy of giving is a little bit like a runner’s high. Which brings me to our next point – generosity takes work.

3. Generosity is a discipline. Giving is rewarding, but it doesn’t come easily, or even feel very natural, especially early on. It’s like exercising, or writing – once you commit and stick to it, as you develop the habit, it becomes more and more rewarding. It feels so good. But it takes work. 

Someone asked me the other day, “Do you like writing?” Honestly, I said not really – at least not the act of writing itself. I labor over words, I get discouraged – and at times in life, I’ve wondered where I’ll find the time (turns out you have to make the time). 

But I do find writing rewarding, and that sense of reward has only increased as I’ve increased writing. I write because I see things that I want others to see, and I want to help others. I now write 3-4 days a week, in the morning. I find it like when I was in college and trained to run the LA Marathon – the more I do it, the more I keep up the discipline, the more natural it feels, and the more rewarding it is. 

Generosity is a discipline. 

On the other side of the generosity is gratitude.

Above: I asked ChatGPT’s DALL-E to create an image that “illustrates the idea that gratitude and generosity form a virtuous cycle. I imagine something that shows gratitude and generosity complimenting each other, reinforcing upon itself.”

4. Gratitude gives me perspective. To me, gratitude is not about my circumstances. Gratitude is about seeing things to be grateful for in my circumstances. Charles Swindoll once said, “Life is 10% what happens to you, and 90% how you react to it.”

5. Gratitude blesses others. When I express my gratitude to others, it enlarges my heart, it makes me feel good, it blesses them, and it strengthens our relationship. My 11-year-old last night said to me, “You know Papa, you are the best Papa in the whole world.” 🥲 Her gratitude warms my heart, and I can also see how it is shaping her heart as well as she expresses that gratefulness.

6. Gratitude is contagious. When we convey gratitude, it catches on. Reciprocity is a powerful force for good. I used to hesitate to ask people to help me. I thought, “I don’t want to inconvenience them,” or “I can do it myself.” But I’ve learned that asking others for help can be a gift to them, if done in the right spirit. And when I express gratitude in response, it leads to more gratitude. 

Gratitude in the City of Brotherly Love

Last week, I was on a business trip to Philadelphia to meet with the senior leadership team of a national charity to do one of my favorite things – lead them through how the 6 Types of Working Genius can be a tool to help them be more effective, create sustainable innovation, and grow. 

They were located downtown, so I parked in front of their offices. I was there a couple of hours early so I thought I would work at a local coffee shop. I paid for parking and found a lovely local coffee shop. After a good work session and a tasty cup of coffee, I strolled back to my rental car to pick up some supplies before heading up to their offices. 

Except my car wasn’t there. 

Instead, there was a red sedan in its place, currently being hooked up to a tow truck to be towed. Looking around, I saw several construction workers nearby. I asked them what was going on. “Yeah, that’s the third car they’ve towed from this spot this hour. The city tow trucks just drive around the block and pick up cars like this all day.” One of the workers said he was towed the past week. It turns out that there was a stretch of the street that was poorly designated as a “press only zone.” I’ve never heard of a press zone for parking, but apparently neither had the other perhaps dozen drivers a day that got towed from the same spot. 🤦‍♂️

They had impounded my rental car, less than an hour before a meeting I was supposed to be leading! 

I had no idea where they had taken it. And worse, my flight home was that night, and I had precious little time to make it to the airport. Now I didn’t have a car, I wasn’t sure if or how I would get it back, if it would be damaged, and I had a critical meeting I was supposed to leading in less than an hour.

I called my client contact. “Oh, are you here and parked?” “Well, about that… I parked in front of the building, and when I came back, they had towed my rental car away.” They quickly sprang into action. It was the lunch hour, and Terry, the building manager, immediately dropped everything he was doing. He took me to his office, located the city impound lot, and was able to find my car in the system using the license plate number. He said, “Let’s go, right now – we’re going to get your car back.” 

After stopping in to say hello to the leadership team, the CEO assured me that all was good and they would be ready to start when I returned.

Terry took me in his own car to the impound lot, and waited with me while I filled out paperwork. It was like a bad version of the DMV (I grew up in California - if you know, you know). I asked how I could contest the ticket and they explained how to do so. I paid an impound fine, and I was free to go.

As I was being escorted to my car, I joked to the lot attendant, “You guys sure seem busy today.” “All day, every day.” “Well, this is my first time to Philadelphia - welcome to Philly, eh?” “Yeah, I’m not sure I would come back.” Ouch. So much for the City of Brotherly Love?

Terry then led the way back to the offices, where he got me a parking spot in their corporate lot.

After all that, I made it to the meeting just 15 minutes late – a small miracle! The senior leadership team was gracious, ready to go, and we dove in. 

By all accounts, it was not a good experience. All things considered, I would prefer I didn’t have to go through what I did. And it seems the City of Brotherly Love could do with an infusion of gratitude and generosity. 

But reflecting on the experience, I’m grateful for several things: 

🙏 I’m grateful for Terry. I got to see him at his best, helping others in need (i.e., me), and I learned about his new baby granddaughter in Phoenix.

🙏 I’m grateful that I was able to pay the fine. Not everyone is able to do that. 

🙏 I’m grateful no damage was done to the car and that I was able to get it back without significantly more hassle. 

🙏I’m grateful that the client leadership team was so gracious, and we had a great afternoon of connection and insight. 

🙏 I’m grateful that I was able to get back to the airport and make it home safely that night. 

💡 Takeaway: Gratitude and generosity are more than complementary emotions – they form a virtuous cycle. One leads to the other, and they reinforce one another.

I’m grateful for you today. Have a great holiday weekend. 

Until next week… Surfs Up! 🌊

  - Dave

P.S. On the subject of contagious gratitude, I’m continually encouraged by the gratitude I receive each week. ☺️

  • Thank you, Dave!  I look forward to each of your emails.  This one truly resonated with me.

  • Totally relate to this!!

  • I would LOVE this, Dave, and your thoughtful generosity and willingness to do this is greatly appreciated.

  • Thanks for giving me something to think about.

  • Thank you, Dave! The Wave Report is something I look forward to reading weekly and have shared it with my team who has enjoyed it as well.

    Thank you. I’m grateful to you for spending time with me each week. 

About the Author | Dave Raley

Consultant, speaker, and writer Dave Raley is the founder of Imago Consulting, a firm that helps non-profits and businesses create profitable growth through sustainable innovation. He’s the author of a weekly trendspotting report called The Wave Report, and the co-founder of the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands. Connect with Dave on LinkedIn.

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