I’ve always done my own IT support for work as long as I can remember. My first real paying job was at Johns Hopkins, where I took over a loosely-organized island of Macs and learned how to optimize, upgrade, and network them all until they were singing in harmony. For a lot of reasons that was my favorite part of that job, actually. From there I took my skills and applied them to various situations, inside bastions of PC’s or design firms filled with Macs—but rarely did I ever need to call on the IT department. At my current gig the whole backend system is a Microsoft implementation, and despite their assurances my Macs would be fine using Sharepoint (“it’s just as good as Dropbox!”) Teams (“it’s just as good as Slack!”) Onedrive (“it’s just as good as Dropbox!”) or whatever service they rolled out, the reality never met up with the promise. There was always some reason why their service wouldn’t work correctly: it completely brought my Mac to a crawl, files got corrupted on their way back to my machine, or there wasn’t enough space on the Sharepoint drive and I was always having to ask them to give me more space.

They fielded a SSO system through a kernel-level nannyware system that’s now keyed to the serial numbers of the company Macs they’ve issued, which means that if I wanted to upgrade them anywhere past MacOS 10.14 the nannyware would immediately take over and install itself automatically, without any option to bypass. I held off for as long as I could but they’ve now got the wireless network in the office tied to SSO as well as printing and a bunch of other services I can’t do without, so I bit the bullet and upgraded my work machine to MacOS 13.3 a few weeks ago. On Friday I had to update my password, which worked fine from Mom’s house. This morning I’ve been locked in an endless loop where I can’t access my machine to access the reset to access my machine, which is the definition of modern technological stupidity.

The modern OS is very nice, and has taken some getting used to, but I like it. Things are peppier, the browsers work better, and there’s some software I use that I’m now able to upgrade to a modern version. The nannyware is there, and I have to use a secondary login to install apps on my own machine (grrrr) but generally speaking it’s OK.

With that experience fresh in my mind, it’s probably time to upgrade my personal machine—a 10-year-old Macbook Pro running a 5-year-old OS. Once I’ve finished paying off our vacation trip, I’m going to bite the bullet and buy my first personal Mac in 13 years. I’ve got it narrowed down to either a 13″ or 15″ M2 MacBook Air. Everything I’ve read says there’s not much point in paying the extra money for a Pro, and nothing I do on my personal machine requires the extra cost. Plus I’ll be able to pair it with my watch and use Sidecar to work more closely with my iPad on illustrations, which I’ve not done much with lately. And I was able to get a sweetheart deal on a lifetime Microsoft Office account for $60 a few weeks ago, which won’t run on this old machine.