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A while back, my friend Tom told me about something he was building called “Drop Dead Generous”. Drop Dead Generous is handing out $500,000. Not to one person. To 1,000 people. Each person gets $500, and they have to fulfill three requirements:
That’s it. No pitch deck. No performance metrics. No viral optimization. Just a question they decided to test: What if we gave more than we took? Here’s the part that intrigues me: Most people base their generosity on a feeling. You wait until you’re moved. But Tom and his team turned it into a constraint: “Here’s $500. Do something kind.” Now you have a boundary. And that’s the key, because constraints are where creativity actually begins. It’s easy to say, “I wish more people were generous.” It’s harder (and much more interesting) to build a system that makes generosity inevitable. With Drop Dead Generous, Tom and his team have built exactly that. People have used the money to upcycle bikes for local kids, host community arts events for working class artists, and create recovery gardens for people fighting cancer. One woman used the money to hire an Elvis impersonator for her parents' vow renewal. Another man used his $500 to purchase meals for vulnerable people in his community. Then, inspired by his generosity, others joined in and raised an additional $6,590, which paid for hundreds of meals. How cool is that? If you’ve ever wished there was a way to put a little more good into the world without waiting for permission, this might be up your alley. There are still 721 grants left. You can join the experiment, apply for a grant, or simply follow along and see what people create. Or just steal the constraint for yourself: What would I do with $500 to create something good? Sometimes the right question is all you need. Happy Friday, friends. Make it a generous one. Kyle Scheele |
One useful idea about creative leadership, once a week
I’ve noticed something interesting about our society’s approach to creativity: we punish it in children and praise it in adults. When adults find creative solutions, they often get rewarded with praise, promotions, or new opportunities. But when children find creative solutions for things, they are often punished. This happened to me all the time as a kid. In high school, I once organized an impromptu fundraiser to buy a gorilla suit (it’s a long story). That afternoon, I got called down to...
They say that you should tackle your most important tasks at the beginning of each day. That way, if things go sideways later, you’ve already accomplished your biggest priority. Which is why, every morning since late 2021, I start my day with Wordle. If you’ve never played Wordle, here’s the gist: Each day, you have six chances to guess a five-letter word. After each guess, the game gives you three colors of feedback: GREY means the letter isn’t in the word. YELLOW means it’s in the word, but...
This week I had three speaking events in 28 hours on opposite sides of the country. Last week I did four events in four cities in five days. It’s the busy season for speakers, and the question I get a lot is, “What about work/life balance?” I love that question, because it allows me to share one of my favorite hot takes: Work/life balance is a myth. It doesn’t exist! At least, it doesn’t exist in the way I often hear people talk about it. People talk about work/life balance as if it is a...