In 2018, back in the Before Time, when dinosaurs, not COVID, ruled the earth, and I still worked in an office full-time, I was introduced to this peculiar, older white gentleman. He had a strong Bahstahn accent and bore an uncanny resemblance — in appearance, attitude, and temperament — to BREAKING BAD’s Mike Ehrmantraut. His name was Stephen, and he was hired to lead a department adjacent to mine. After a couple of interactions, a few things about Stephen quickly became apparent: he was wickedly funny, loved to challenge people to think differently, neither suffered fools nor tolerated bullies, and was fiercely protective of his people. Over time, it would be my great privilege to become one of “Stephen’s people.”
Stephen Flannery died a little over a month ago, unexpectedly, and under circumstances that have made his death even harder to reconcile than it already would have been otherwise — but those circumstances are not mine to share. It’s been five weeks, and it still feels surreal.
We had a “celebration of life” for Stephen at work last week — a phrase and event Stephen would have professed to loathe, even though on the inside he would secretly be flattered and happy. Over a hundred people from multiple states attended in person and another 150 called in on Teams — all of them showing up to share stories about a man who’d been gone from the organization for six months. That was the kind of figure Stephen was. Nearly everyone there cherished Stephen in some fashion. I say “nearly” because I do not doubt that a few folks secretly showed up just to make sure Stephen was, in fact, dead. This makes sense when you understand how someone once described Stephen as the best friend you could ever hope for or the worst enemy you could be confronted with. I remember how delighted Stephen was when he related that story to me. Because that was Stephen — a man for whom there was very little middle ground.
Within six months of meeting Stephen, the department in which I worked experienced several sudden upheavals. I made it six months before staying in my position became untenable. That’s when Stephen offered me the opportunity to come work for him in an entirely different part of the organization, one which I knew fuck-all about. I pointed this out and he told me he wasn’t hiring me for my subject matter expertise, he was hiring me because I was a good leader. It was the best career move I ever made.
Over the next five years, I got to know Stephen better as he progressed from colleague to mentor, to one of the best leaders — and people — for whom I’ve ever worked. Somewhere along the way, we also became friends.
As I noted earlier, Stephen left the organization in January 2023. This should have been a major bummer, but our small team was strong and Stephen’s successor appeared to be (and was) a good fit. There was also the hint that Stephen would one day ask me to come work for him again. Stephen and I actually ended up talking more after his departure than when we worked together, an unexpected but delightful turn of events. We still had weekly 1:1s, but the frequency of our texts increased to multiple times a day: sharing Words With Friends scores, sending profanely funny TikToks back and forth, sharing recommendations and commentary on books and movies, plus the normal, everyday life shit. He would randomly send me books he thought I would like, including the Folio Society editions of JURASSIC PARK and THE LOST WORLD mentioned in this post. (I sent him a very nice thank you note and told him not to do it again.) Stephen was a major encourager of my writing, even offering a few months ago to put me up in his house for my own personal writing retreat. I never had the chance to take him up on it.
I’ll close out this ramble by sharing a message Stephen sent me a couple of months back, that I have scribbled down on a post-it note inside my desk.
I never tire of your writing. Check. I so look forward to your writing. Paternally proud. Fraternally envious. Keep inspiring.
Stephen was a lion of a man; a mentor, a devil, and my friend. I miss him.