I had coffee with a founder a few months ago who told me something that stuck with me.
He said his biggest regret wasn’t a bad investment or a hire that didn’t work out.
It was a folder.
A folder on his desktop labeled “Follow Up,” full of names of people he’d met at conferences, intros he’d been given, conversations that had gone well.
All of them just sitting there.
He said he opens that folder every few months, feels a wave of guilt, and closes it again.
I think most of us have some version of that folder.
Maybe it’s not literal. Maybe it’s a drawer of business cards, or a LinkedIn tab you never quite get to, or a text thread that ended with “let’s grab coffee soon” eight months ago.
But the folder exists.
And the reason it exists isn’t because we don’t care about the people in it.
It’s because we don’t know what to say.
The meeting felt complete on its own. The conversation had a beginning, middle, and end. Reaching back out feels like it requires a reason, and most of the time we don’t have…
