Something you should know about me: if you have a tattoo, and you’re sitting next to me, and it’s visible…I’m going to ask you about it.
It won’t be weird, I promise—I’ll just ask you to tell the story behind it. And then we’ll be friends.
The fundraisers I know and work with aren’t an especially heavily tattooed lot, but I want to stand out from the crowd! Should I get a fundraising tattoo, Substack?
Let’s see what AI thinks and watch Kitty freak out in the Comments.
I generally don’t make life choices based on Artificial Intelligence’s advice, but let’s play around a bit with ChatGPT—a tool that fundraisers are still wrapping their minds around.
Geez! It was a “yes” or “no” question, ChatGPT! Skynet would have given me a straight answer! (Google it, kids). Here’s a couple tattoo images Chat GPT dreamt up for me:

To my mind, fundraising struggles to know when and how to apply AI. And for good reason! So much of fundraising boils down to relationships and it’s unclear how AI can/will/should spur deeper relationships with donors. Or even if we should expect it to. AI and human relationships feel antithetical to each other.
But I do think there’s some suggestive possibilities for AI within fundraising whenever we’re ready to take the plunge. Take another look at what ChatGPT spit out above in response to my question and you’ll see what I mean. It didn’t really answer my question; it gave me different angles to approach my question in terms of “Professionalism and Audience,” “Design Choice,” and “Personal Significance.” Perspectives that didn’t even occur to me when I asked the question.
In short, ChatGPT isn’t daring me to get a tattoo, it’s not driving me to the tattoo parlor after a night of heavy drinking, and it’s not letting this adorable dog anywhere near me with a needle:
ChatGPT gives me a range of information and perspectives to bring to bear on my decisions. For fundraising, this means AI could help me help me drum up ideas for engaging new people in our work. Or give me suggestions for how to connect with different generations of donors. Or call my attention to materials I can read to learn more and do more with my donors.
But it can’t do the engaging and connecting and reading for me.
That’s still my job.
I’m not getting a tattoo. Sorry to disappoint. But here’s one last picture for good measure:

The best way to think of fundraising and AI right now is like one big playground. We’re all figuring out what works, what doesn’t, what are the rules, and who’s playing. The relationship between fundraising and AI is still unfolding, which makes it a particularly exciting time to be part of this profession.
So play around and have some fun with it. See what tattoos it thinks you should get! Or just ask it random questions and see what it kicks back:
After asking about tattoos, Friends, and jumping double dutch, I feel like ChatGPT and I are friends. Which is sort of stupid of me (and may be the plot of the next Terminator movie) but all relationships have to start somewhere!
Do you have any tattoos, ChatGPT?
Daniel. I don’t “freak out”. I quietly and respectfully ask you to explain your life choices. Also, the 501(c)3 tattoo is something a hooker might have, to encourage her clientele to tip well, to ensure a comfortable retirement.
If you get a 501 c 3 tattoo, I'll pay for it!!! Seriously!