OpenAI: a writing retreat with three women, a bald bearded man, and a large white dog. Not sure where the third woman is.

I love your blog.

Some thoughts from my weekend about how I don’t think of myself as a writer or even someone in media. I’m wrong.

Tony Stubblebine
3 min readNov 17, 2024

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Sarah is writing a book and in an on-brand-for-her move she has recruited two other book writers into a writer group to give each other support, feedback, and motivation.

I don’t think of myself as a writer and I don’t normally think of Sarah as one either (we are both tech execs, IMO).

But this weekend Sarah’s writer group came over to our house for a “writer’s retreat.” They all have nearly finished books.

I tried to stay out of their way other than joining them for dinner. Over one of these dinners it came out that a friend of a friend had done a solo writing retreat at our house last year while we were out of town.

This friend of a friend has a Pulitzer. I must have known this, and I’m surprised to have forgotten it because normally I am a shameless name dropper. Things like Pulitzer winners in our house usually stick.

That story also reminded me that our friend Alex has twice borrowed our house for a writing retreat with her own writing group.

So I was left wondering: how did it come to pass that there are so many writing retreats at our house given that I’m a software engineer turned entrepreneur turned self-improvement aficionado? I’ve never had a CEO retreat, hackathon, or meditation circle in my home.

Belief change is hard and it often comes from cognitive dissonance. That’s what is happening to me in this post. Maybe I’m not who I think I am?

I wrote a book in 2003. It sold north of 50,000 copies. Normally I discount the idea that I’m a book author because that book was 95% reference material. So that doesn’t qualify me as a writer.

Sarah has written two books, has at least 30 stories published in the NYTimes, and had a career as a freelance journalist.

But even then, the bulk of what I’ve seen of her career was in leadership. We met when we were both getting our first management assignments. Years later we were both CEOs overseeing identical budgets. So I see her like I see myself, tech exec.

That first time meeting Sarah, at work, was based on a personal factoid that I knew about her. She was running, for fun, a movie review blog that rated each movie on the appearance/quality of dogs and shoes (and do things blow up).

I had read her whole blog front to back before running into her at an all hands company event. That led to me delivering the most earnest turned-into-a-pickup-line line of all time, “I love your blog.”

I really meant it. We’re coming up on twenty years together.

That company we worked at was a book publisher by the way. Maybe I got lost doing other things for a few years. But then I got pulled into Medium as a blogger and then publisher and then staffer.

I’m not sure how this happened because in High School I was firmly on the math track: honors math to computer science college degree to software engineering career. That’s who I thought I was.

But I haven’t written code since early 2022 and even that was very casual. Coding hasn’t been my primary job since 2006.

Meanwhile, my house is home to writing retreats. My significant other is writing a book. I’ve written 746 blog posts just here on Medium alone. I run a blogging company.

So, cognitive dissonance accepted. This is a writing household.

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Tony Stubblebine
Tony Stubblebine

Written by Tony Stubblebine

CEO at @medium. “Coach Tony” to some.

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