Ask Paul: February 17 (Premium)

Happy Friday! We have a busy weekend coming up with our house going on the market, but first, here’s a great set of reader questions to keep my mind off that.
Yin vs. yang
will asks:

Yin vs Yang.  It seems over the past couple of years Microsoft is doing both good and bad, but they never seem to excel much.  There are some recent examples of this such as the Bing AI post you did on how dark this new improved AI is supposed to help us but can lead down some very dark holes.  The other is Windows 11 with an updated UI, yet with the inclusion of more ads and data being collected.  Another is Edge becoming a good browser that works well on almost everything but includes so much junk/add-ons the basic browser is lost.  Or how about how my premium version Outlook.com email gets several spam mails in my inbox daily, yet the same platform that powers O356 business users can block pretty much everything?

Ah boy. It’s like you’re scratching at a scab that I’m desperately trying to avoid to preserve my sanity. Where to start?

I guess there are two forces at work here.

The first is the broader strategic shift at Microsoft, which has been promoting its cloud computing efforts over all else because that has driven the stock price to stratospheric levels. And it’s not just public posturing: we’ve discussed before how Terry Myerson was given the horrible task of making Windows make sense in this cloud-focused Microsoft back when he ran that business. And that one result was Windows as a Service (WaaS), a method by which Microsoft updates this monolithic, legacy software stack as if it were an online service. There were other byproducts, of course, one of which led to his ouster: Windows only makes sense at a certain volume, and so Terry was bullied into getting Windows 10 to one billion users more quickly than was possible. (Announcing that goal was probably his fault/responsibility, but the shifty methods he used to try and reach this unobtainable goal were absolutely his fault.)

Tied to this, of course, is the reality that Windows is not the place to be at Microsoft now. If you are anyone who’s anyone or seek to be, you work on high profile/high reward businesses or you try to create them. This is the opposite of a virtuous cycle: when you drive the best people away, the product suffers, and as the product becomes less desirable, the best people stay away. Etc.

The second point is related and the best description of this problem I’ve seen comes from Corey Doctorow, who describes the effect you’re seeing as “enshittification.”

“Enshittification is a seemingly inevitable consequence arising from the combination of the ease of changing how a platform allocates value, combined with the nature of a ‘two-sided market,’ where a platform sits between buyers and sellers, holding each hostage to the other, raking off an ever-larger share of the value that passes between them,” he writes. “When a platfor...