From the Editor’s Desk: Nothing Works (Premium)

Nobody likes to be criticized, but there is one bit of feedback I get that’s as common as it is unwelcome. It’s that I’m negative.

Many of you are probably nodding your heads in agreement with that, and while I can’t pretend to not understand the sentiment, I don’t like it. And for so for many reasons. One of which is that it’s obviously true.

To confirm this, I asked my wife if I was negative. After repeating the question back to me, a classic stalling technique, she finally responded with, “Well, sometimes.” No, no. Everyone is negative sometimes. I mean, overall. This time, a pause. To which I said, “It’s OK, you’re not going to hurt my feelings. I’m just curious if you think I’m negative overall.”

She finally answered, “Yes.” Which obviously hurt my feelings. Kidding.

Look, I rationalize my behavior just like anyone would, but I also take it a step further by trying to turn this judgment into a positive. I argue, for example, that negative people will never be disappointed because they always expect the worst. I believe that my worldview is part of what makes me good as a reviewer or industry commentator as I’m less likely to be snowed under by marketing drivel; I am not a cheerleader, as so many are.

And I’m not a swirling cesspool of negativity all the time. I also make a point of identifying positive influences in my life, adopting those traits where possible, and making sure that the people I care about know that they matter to me. Heck, I’m even taking medication in part to address this issue. Collectively, this is all about me trying.

And I can praise those things I may also criticize—Big Tech companies and their leadership, products, and services most often—when warranted. It’s not contradictory, for example, for me to have two different angles on tech service I rely on, like OneDrive, one in which I praise it for its reliability and the other in which I damn it for its escalating nagging and ignoring of my preferences. Nothing is perfect.

But it’s worse than that, and I think that fact cuts to the core of why this negative thing bothers me so much. We are in some ways the product of our experiences. And by moving into a career in personal technology, something that was more circumstance than choice, I inadvertently put myself in the middle of an industry that moves fast, always changes, and breaks things constantly. Nothing works. Like, ever.

OK, not literally. But it feels that way sometimes. I’m not sure a day goes by when everything I use just works perfectly. That seems like something I’d notice.

The sweeping enshittification we see everywhere in our industry isn’t helping. It wreaks havoc with my sense of right and wrong on one level, but also on my way of doing things. With a limited ability to remember details, I will relentlessly figure out how something works, or the best way to do something, and then utterly forget the why or how of it once it’s up and running. A set-it-and forget-it kind of mentality, if you will.

In the best of times, this can be confusing if I need to reexamine something I already figured out. A good example of that is the way that I handle multiple email accounts because there are several different approaches one might take, and at least a few seem viable to me. But at some point long ago, I experimented with each approach, chose the one that works best for me, and then I even reexamined this topic later and came to the same conclusion again. And so now I know that what I’m doing is “right,” for me. But if you asked me about it, I’d have to look it up.

(If you are curious, I did look it up. I push all of the emails from all my accounts through a single central account that I configure so that it can send responses as is from any of those secondary accounts. The pushed emails are archived at the sources so that those inboxes are always empty. I use a web interface for this central account on desktop and the Gmail app on mobile. I’ve written about all this … somewhere.)

But in these days of enshittification, it’s more complicated because the products and services we all use are literally getting worse. And this requires us—me, certainly—to reexamine what we use and the ways in which we get things done more frequently. What was always a job becomes more of a chore. And this weighs heavily on the overtly negative. You know, people like me.

Here, the obvious example is Windows. Over the past year, I have documented and re-documented how I believed that Microsoft was updating this product again and again over time. This was necessitated because Microsoft kept moving the goalposts, if you will—by changing its strategy almost month-to-month this past year in particular—and never bothered to tell anyone what it was doing. And so I did what I could do, which was to observe what was happening over multiple PCs, examine what little Microsoft did say on this topic, and make some educated guesses based on experience.

And at some point, I ran into that inevitable bit of feedback. Someone who doesn’t understand why this matters, not just to me, but in general, and why I even worry about this kind of thing.

I find that response stupefying because it feels so obvious to me. I’m not the teacher in Back to School—“he really cares … about what we’ll never know”—I’m in the trenches. I need to document how Windows works, especially in my books, like the Windows 11 Field Guide. And part of my value to the outside world is that I should be able to state, with certainty, what will and will not happen when readers do something particular.

But Windows 11 is so full of qualifications it’s almost become a giant asterisk. Features are announced but not deployed to everyone on a predictable schedule. Some never arrive at all. Sometimes there are multiple versions of some app or feature, and … it just depends. This is not certainty, it’s vagueness. And to my set-it-and-forget-it brain, it’s an anathema. It’s a burden.

What I’m looking for, always, is something that can be repeated, documented, and then will always work for others, freeing me to not worry about it anymore. This is the opposite of anecdotal: It doesn’t matter if it only happened once. What matters is that it always happens predictably. And that is not where Windows is today.

So here we are. Nothing works as it is. But now Big Tech is changing things in ways that feel arbitrary, forcing us to wonder what motivates them to make actively things worse for their customers. And it’s happening all around us. It’s like a slow-motion horror movie.

This past weekend, I made some big configuration changes in OneDrive as part of my trying to fix something that’s gotten worse this past year. This was pretty scary, but I was surprised that, for all of OneDrive’s recent issues, that change seemed to work flawlessly and will help fix the problem. And so that’s a nice little win that I’ll write about at some point, once I’ve given it time to make sure all is well. But I also factory reset my desktop PC, using that three-step process I outlined to restore it to a perfect, pristine state with the OS, apps, and my data all configured exactly as I wanted. It felt good getting this done because it was overdue. The PC had been having all kinds of issues.

And then I had to record First Ring Daily with Brad this morning just like every other day. And I discovered that my Focusrite box, which connects my microphone to the PC over USB, wasn’t found by Windows. All the drivers are up-to-date, I have the latest Focusrite software, I performed all the obvious troubleshooting steps, and … it just ain’t there. And I know what I’m doing. I always wonder how “normal,” non-technical people deal with this kind of uncertainty and unreliability. I’m honestly not sure how or if I can even fix this now.

Because nothing works. It’s just so perfect. And so negative of me to point it out, I guess. But that’s my final defense: Celebrating that most of this PC is fine right now just doesn’t make sense to me. This kind of thing, this relentless issue, is a big part of why I can be so negative.

I think it’s understandable. But then I would.