I wrote something upsetting to people on the Internet. I mean, more than usual. I’m used to be people disagreeing, but the negative response caught me off guard, which is interesting in itself. What can I learn?

Here’s what happened: I wrote a response to a big story about a death of a guy’s father at an Airbnb, published in Matter (a publication owned and operated by Medium, of which I am CEO). I posited what I thought was an interesting question (in about 30 seconds) and went on with my day — while the responses to me were having me voted off Medium if not the Internet altogether.

In retrospect, here’s what I miscalculated:

My tone came off as lacking empathy for Zak Stone, the writer of the original story. He told a tragic, personal story and I’m up in there saying, yeah yeah super sad, BUT… (more or less). My immense sympathies go out to Zak and his family. I didn’t bother to say that, though. I’m generally not the best at judging how other people are going to feel, but here is what I think was the exacerbating factor: I read the story days before I wrote that response. As a result, I wasn’t in the same emotional state as those who read it right before they read my response.

Obviously the context and tone of a conversation have a huge effect on what feels appropriate to say. If we were having an intellectual argument over dinner about an accident that lead to a death and we had no relationship with the affected parties, our tone would be much different than if someone personally involved just told us the story and was at the table. The story was both about a death and about Airbnb and how it might improve safety generally. I was commenting, intellectually, on the Airbnb part after the emotional weight of the story had lessened for me. But it was very fresh for those reading my comment. (Note to self: Consider where your audience is coming from.)

The second dumb thing was I assumed people would know I was talking about the mocked up Airbnb images — not the personal photos — when I said “the images are a bit much.” The third thing was I didn’t say what I meant by that (until later). Also, it probably seemed like I was talking to Zak, the author, when really I was aiming that at the Matter folks. Anyone reading the story was feeling a lot of sympathy for the Zak, so saying he had bad illustrations seemed dickish on my part. I had a different association with the story because I knew the Matter editors were responsible for the images. (Note to self: Don’t assume so much — duh, it’s the Internet.)

I had told Mark Lotto this privately beforehand, but he also knew it was his call and chose to leave them in. He and his colleagues make tricky calls all the time, and I respect them immensely. By disagreeing public I felt like I was treating Matter as I would any other publication and honoring (and demonstrating) their independence. I felt like was a simple editorial disagreement, which they would take in stride, and I stand by my opinion on the imagery. But this was not necessarily a helpful place to share it. (Note to self: Keep those conversations private.)

Others were pissed at me because they dislike Airbnb — either what they stand for or what they do or both — and it seemed like I was defending them in the wake of this terrible death. That’s not a popular position at the bottom of this particular story, but that part isn’t as surprising. And, really, I was asking an honest question I was curious about (whether they’d feel differently if it were Craigslist or VRBO). I had an opinion, but it wasn’t well informed (which is why I stated it as a question). Several people I talked to offline before all this had the same thought/question, so it seemed interesting enough to put out there. Some people appreciated the question. Others, like Glenn Fleishman, gave me reasonable explanations why the expectations are different for Airbnb. Successful Internet discourse!

Other things I learned:

  • It’s still possible to offend people and be caught off guard by that 20 years into doing this Internet thing. Navigating human emotions via text on screens is tricky.
  • Navigating Medium response threads really sucks. We knew this already (and are working on it now), but I learned it sucks for another reason. If you want to follow up on something you said, there is not a good way to do it. I replied to a few people who replied to me, but not all, because it was too tedious. We still haven’t cracked the nut on serious back-and-forth. We’ll work on that too.

Lessons learned. Much to do. Thank you for your support.

In the immortal words of Dave Winer: “Still digging!”

Written by

CEO of Medium, partner at Obvious Ventures, co-founder of Twitter, curious consumer of ideas

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