As a kid I’d prowl graveyards with my mother, tightly holding sheets of wax paper and thick, flat Crayolas. Macabre backdrop for sure, but our interest was in art not mischief. Upon discovering a tombstone with especially interesting inscriptions or carved pictures we’d overlay the wax paper and rub the crayon up and down the sheet. The resulting artifact was a color representation of the words and images beneath. You can look at this rubbing of a leaf and imagine the equivalent.

Besides an awesome relationship with my mom (these weren’t even close to the weirdest stuff we did together), those days left me with an appreciation for how people told their final personal story. Around New York City suburbs and occasional trips to New England I read centuries worth of lives lived – maybe this was the spark which eventually turned me into a history major at college. Died young. Lived long. Families buried together over generations. My thoughts kept coming back to how they spent their time and the identities they chose to project from the headstone. Father. Son. Husband. These were common. Friend. Veteran. Those appeared frequently as well. Less so was your profession – maybe the oldest graves referenced a trade, but as you crept towards the late 20th century the idea of your work being important enough to chisel started to disappear.

Although I wouldn’t be able to articulate myself quite this succinctly until I reached my early 20s, it was around this time that I started to believe you should only work on projects worthy of your tombstone. Why otherwise spend thousands and thousands of hours doing something? And that if I had opportunity to use this heuristic as a filter, damn right I was going to do so.

And so I did and I have. I’ve worked at companies and in roles that I feel strongly enough about to make eventually part of my resting legacy. Not to the exclusion of the other identities and relationships I hold dear but not compromising either.

When I’m talking with a startup founder about their company and whether Homebrew might be the right partner for them, I probably over index on “founder < > market fit.” Why does this problem matter to them? Why do they want to work on it for the next ten years? And what would make them proud? Not just what would make you successful, but what would it mean to be proud of what you built. The financial outcome can (must!) be a part of that, but I think it’s a leg of the stool.

Sometimes I’ll say it directly: I want you to care enough about this company, and ultimately be proud enough of the outcome, that you want to put in on your tombstone, not just your resume.

This doesn’t mean sacrifice everything for your job. This doesn’t mean neglect other people and pursuits you care about. This doesn’t mean win at any cost. This does mean don’t be afraid to apply yourself to something that feels like your life’s work. And if you’re not currently doing that, what’s holding you back?

(1) In also a cute play on words, a “tombstone” is the term used for the small celebratory statues that an investment bank gives out for a successful transaction (IPO, M&A, bond issue, etc). So if you’re founder who ends up building something “tombstone-worthy” it kind of has a double meaning in a way that makes sense 🙂

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