014: hats, haircuts, or tattoos
soft launching my new side project
I was doomscrolling yesterday and came across this IG reel.1
All decisions are hats, haircuts, or tattoos.
A hat is something you try on. If you don’t like it, you take it off, no harm done.
A haircut is a bigger deal. The consequences last longer, but it grows back.
A tattoo is forever. Well, not exactly but it’s really, really painful to undo.
Publicly committing to writing weekly felt like a ‘hat’ type decision back in January.
Until some of y’all started calling me out for missing a week… and now a full month!
It definitely feels like a tattoo now.
But let me explain my radio silence…
“That’s just how things begin.”
Starting things from scratch is just hard. Everyone already has a full plate. You’re asking them to add something to it.
I’ve been approaching these collaborative conversations with what’s in it for you, what’s in it for me. I lay out our shared upside as cleanly as I can. Even though there’s really nothing concrete, as of today.
Most of them took it in a new direction:
“You sound really enthusiastic about this new thing, and I know you’re a sincere guy that’ll take it seriously.”
So they’re saying yes anyway.
Some of them have watched me for years. Small things, mostly. Apparently those count.
It blows my mind. I’d like to think I deserve the trust but I don’t. There’s so much I’ve said I’ll do that I haven’t done yet.
I’m grateful.
Maybe that’s just how things begin.
“More on both soon.”
So what’s the new thing?
Getting people working inside, outside, or alongside multi-generational business families to tell their stories, so that we can learn:
About how nextgens plan their entries as nowgens plan their exits.
About how family enterprises evolve to spawn family offices, family foundations, or family councils.
About how families cultivate human, social, intellectual, and spiritual capital. Not just financial.
I know who’ll listen closely.
A small room for those who’ve been there. Handpicked by myself.
A podcast for everyone heading there. Especially Gen Zs. I want you guys eventually in the room.
Most of these stories don’t get out of the room they’re told in. So I’m building one that does.
Time to work that enthusiasm and sincerity of mine to seriously get people talking.
If you want to be in the room, reply with a few sentences. Who you are, where you are in your own passage, what you’d bring. I’d love to see if you would be a fit.