From the Editor’s Desk: Stories I Wanted to Tell (Premium)

My mother is an endless source of stories, most of which are sadly unkind and of no interest to anyone outside my family regardless. But she has her moments. Years ago, we were speaking on the phone and she asked me about work. What I do for a living is something she’ll never truly understand, but she’s proud of me regardless, and I’m pretty sure there was at least a decade there when she thought I worked for Microsoft. But on this occasion, she asked how Microsoft was doing, most likely because she believed if everything was going well for the company, I’d probably be doing OK too.

They’re doing great, Mom, I told her. Gangbusters.

“What about that other company?” she asked.

Other company?

“You know, the other company. There was Microsoft. And then there was … that other company.”

Apple?

“Yes, that’s it. Are they still around?”

Why yes they are, I told her. They’re doing pretty good.

Apple was, of course, the biggest company in the world at that time. As they are now. A nice little business, apparently.

I was reminded of this last week when my mother tried to reach me repeatedly by phone but I kept missing her because we were traveling. Also, her birthday was last week and so I wanted to just call her then. But when my phone kept ringing during the flight to Dallas, I finally texted her back to let her know I was in the air. Maybe this could wait.

It turns out, she wanted to make sure my daughter Kelly was OK: She lives in Charlotte, North Carolina, and my mother had heard about the hurricane that devastated Asheville. Charlotte is pretty close to Asheville, but she didn’t have any issues, and all was well. Which is what I finally told my mother when I did call her back to wish her a happy birthday.

She asked about the travel I had mentioned as the excuse for my tardy call back. I explained that I was in Dallas for work.

“Dallas?!” she asked as if I had said we were in Antarctica.

Yeah. I’m actually speaking at an event here.

“Speaking?!” she asked as if that were just as non-sensical. On that, she might have had a point.

Yes.

“What are you speaking about?” she asked, making me think again about this notion of elevator pitches, a construct I sometimes use when I need to summarize something that may normally require a lengthy discussion into a very short description. And this was complicated, especially since I was talking to my mother, someone so non-technical that she doesn’t even appear on a spectrum that might measure one’s acumen; she’s off in space somewhere. Hm.

I started to explain that I was speaking about Windows and AI, knowing the deliberately provocative title of this talk, Windows is Dead and Copilot Stole Your Job, would be far too much for her to handle. But I had been thinking about the talk, of course, and the framing I had finally settled on. So I simply went with that.

This year is my 30th anniversary in the tech industry, I told her. And so a lot of it is just stories I’ve accumulated.

There was a pause.

“I’m just glad to see you finally stuck with something,” she finally came back with. An answer so hilariously off-base that I was momentarily speechless, a skill my mother does possess. I mean, I’ve been married for 34 years. I can see things through.

This conversation occurred right before I left my hotel room in Dallas, took the elevator down to the first floor, and walked over to the conference area, where I walked into the then-empty room to prepare for my talk. It’s possible it threw me off a bit. It’s more likely that it didn’t matter. I’m not a very good speaker, despite having done this type of thing for over 15 years. In my experience, there are two types of speakers, those who memorize a presentation and can rattle off the same content exactly, every time and on cue. And then there are those who freewheel it. I’m in the second category, and have always been uninterested in basically reading slides. The people in the audience can do that.

But it’s more than that. I’m more interested in interacting with people than I am in talking at them. In most of the talks I’ve given, the Q & A at the end is far more rewarding than the talk itself. Which I suspect is true for the attendees as much as it is for me.

I didn’t go into this easily. When Tony Redmond–a longtime friend and colleague–reached out to me about doing this back in the spring, I was a bit taken aback. Speaking publicly is one of many things that had fallen by the wayside since the pandemic, and while I hadn’t thought about it explicitly, my immediate reaction was, no thanks. But he told me Mary Jo had spoken the year before, and so I reached out to her to see what she thought. Mary Jo, like me, isn’t a fan of public speaking. But she had a great time, really enjoyed the people who organized the event and the attendees, and recommended I do it. And so I did.

And then I spent the next six months repeatedly reorganizing and rewriting this talk, whose provocative title can be tied directly to Tony. We’re a lot alike, the two of us, maybe a little too much. We have the same sense of humor, the same outward grumpiness that masks a deeper caring for those around us that many might be surprised by. Plus, I hadn’t seen him since before the pandemic. My whole life seems to be divided by that awful experience, that lost year.

The problem I had was paradoxical. I didn’t want to spend too much time just blabbing on a stage, preferring instead to focus on the Q & A. But I also had these ideas, these many connections between what Microsoft and the broader tech industry are doing with AI now and many events of the past. And this talk could easily be two hours long. I only had 30 minutes. Plus 15 for Q & A. And then I had to cede the stage for the next speaker.

So I whittled it down. Reshaped it repeatedly. Changed the focus from this to that and then back to this. Finally, I called Mary Jo the week before the show. I had even never thought to ask her what she had talked about at the event last year. Interestingly–perhaps not coincidentally–there were two big overlaps. But one general theme, which she described as “where Microsoft’s needs and those of its customers diverge” hit home. She was describing enshittification. And I live and breathe enshittification. This is, after all, what our industry has become.

And so I gave my talk. I went over time, of course, as I knew I would, leaving less time for the Q & A than I wanted. But more problematically, I had some stories I wanted to tell that I hadn’t gotten to. After all the honing and whittling, I still needed more time.

The most important one you may have heard before, but it’s a good one and relevant to this shift to AI.

Many years ago, back when Ignite was called TechEd, my company–which was the publisher of Windows IT Pro Magazine, originally Windows NT Magazine–was hired by Microsoft to host pre-con (pre-conference) sessions ahead of the opening day and keynote. At that time, the industry was struggling with the big push at that time, which was away from on-premise infrastructure and to the cloud. Microsoft was pushing the cloud heavily, just as it’s pushing AI now, and it was meeting a lot of resistance. Just as it is now. I recall that the understanding at the time was that the “low-hanging fruit” for cloud–the service that was such a no-brainer that business customers would overcome their reluctance–was email, thanks in part to the complexity of hosting Exchange in-house. And that we later shifted to storage. I remember a lot of things, I guess. Some better than others.

But I will always remember this quite clearly.

We hosted two pre-con sessions that year, in adjoining ball rooms the size of football fields. Mike Otey hosted the developer session, which annoyed me before the event, and even more so afterwards. And I hosted the IT pro session. I could hear laughter and even cheering from the room next door: Developers were overjoyed that they could write the same code yet again, this time for the cloud. But my room was like a funeral. To this audience, the cloud was unwelcome.

One guy raised his hand to ask a question, and so I pointed to him and he stood up.

“You mean to tell me,” he began, tipping me off this question wasn’t going to end well, “that my last act as Exchange administrator is going to be me handing over the keys to the kingdom to Microsoft?!”

There is no good answer to this question.

So I just said yes.

And then explained that he had entered an industry that was best known for its constant, disruptive change. That he had gotten maybe a little too used to a world in which there was just Exchange, that his only challenge was managing migrations between every other Exchange version. That he had stopped learning. That he had, in effect, made himself less valuable to a company that would better off if it did not have the expense and complexity of an on-prem Exchange infrastructure. That he was now in the worst possible position to make the right decision for his employer because that decision would mean he needed a new job.

I can’t imagine this answer was in any way pleasing. But it was correct in the sense that things change. And the parallels to today with AI are obvious. People are as worried about job losses with AI as they are in the coal industry. This is what I call a “now” problem, meaning that it’s very real right now because it’s happening to real people and there is no good solution. But future generations will look back on the jobs of today–Exchange administrator for a single company, coal miner, whatever–and wonder why they even existed. Or at the very least not care that those jobs are gone. We don’t light a candle for all the lost stagecoach driver jobs, after all.

This is what technology does. It brings advances. Advances that take away what used to be needs. In the generations before photography existed, families hired oil painters to create portraits they could hang on the wall, memorializing the people in that time. Photography, once the province of experts, became mainstream and is now so common we all carry around a camera in our phones in our pockets. There are still oil painters, of course. And professional photographers. But those jobs aren’t particularly common or lucrative. Things change.

I often think about the impact–if any–that I have in using AI to create images for this website. Am I taking away jobs?

I don’t think so. My best friend’s wife is a graphic artist and, regardless of skill, it’s not possible for her to do what AI can do: Create four images in seconds based on a simple description and then fine-tune the one I like most until it’s exactly what I want. She wouldn’t be able to do it quickly enough, and she wouldn’t be able to do it inexpensively enough. And if she was the only option for that task, I just wouldn’t do it.

I also have enough self-awareness to know that my job could be largely done with AI, and soon will be, especially the news stories but also, eventually, the thought/opinion pieces. That future generations might look back on this time and wonder how it could ever have been a profession. Even writers of fiction, like Stephen King, will be replaceable. AI-written content will win awards. It will be better. Things change.

But it’s on all of us to change too. Sometimes it’s easy. More often, it’s not, as is the case with the coal miners in the Appalachians who suddenly find themselves in a place with no viable jobs, and no real skills to find new ones, even if they did exist. It is perhaps ironic that the advice often given to these people–just learn software programming–is about to be taken away by AI too. Either way, it’s sad. It’s a now problem.

I got some of this out during the talk in Dallas. But not all of it. That’s what happens, I guess, when you freewheel and don’t have enough time. But it also hits on the central issue I had heading into the talk. I wanted it to be light, for my talk to be a less technical interlude between technical discussions led by subject experts. But, I also realized very early on that I had something serious to say. These are difficult concepts to bridge or commingle. And as is so often the case, I don’t think I did right by it.

But I got some of it out. And in the end, all I have is the stories, a curated subset of my memories commingled with facts, misunderstandings, and lessons learned. It’s enough.