My Friend, Stephen

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 old white dude who had a strong “Bahstahn” accent and who bore an uncanny resemblance — in appearance, attitude, and temperament — to Mike Ehrmantraut from BREAKING BAD. His name was Stephen, and he was brought on to lead a department adjacent to mine. After a couple of interactions, a few things about Stephen quickly became apparent to me: he was wickedly funny, loved to challenge people to think differently, did not suffer fools or tolerate bullies, and was fiercely protective of his people. Over time, it would be my 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 than it already would have been otherwise — but which are not mine to share. Five weeks later, and it still feels surreal.

We had a “celebration of life” for Stephen at work last week — a term 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 their favorite stories about a man who had left the organization six months previous. Nearly everyone that was there cherished Stephen in some fashion. I say “nearly” because I do not doubt that at least 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 area in which I worked experienced sudden upheaval. I made it another six months before it became untenable for me to remain there. 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 of this year. 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 once again. It was an unexpected but happy surprise when Stephen and I actually talked more after his departure. 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.