I think yes and no. After working for 7 years+, you will hit a plateau. To break through, you will need to study on your own free time. That's because most individual work doesn't get harder after a certain level. It is the scale of it that makes the work difficult.

Thanks for the advice. I figured it would be something like that but thought this is probably the best chance I have to take a stab at it.

I’m an infra guy, and I’ve had two unexcellent jobs in a row now where I’m the only Linux person, and the most critical things run on Linux, so I spend the majority of my time on break/fix situations and trying to remember what the fuck I was doing before someone bothered me with another broken service. To make things worse, management was and is chaotic and disorganized that I can’t take time to complete a single project at once (and in the case of my current role, an actual barrier to progress, I’m currently getting blocked on something because I haven’t tested a particular method of copying a script to target hosts for a process that we do only twice a year, the difference is as trivial as using rsync instead of scp, but not exactly since I don’t want to give exact details, just in case!). I can tell that I’m not learning anything, and in many ways, my skills are regressing (as has become apparent through all the interviews I bombed in the last six weeks).

The problem is that I’m so irritated and demotivated by this job that I don’t want to look at a computer after I’m done. I don’t want to be in my office after I’m done. I only go in there if I forgot a drink or something on my desk. I need to figure out a way to upskill outside of work since it’s so clearly not going to happen at work, but the mental “anguish” (not quite anguish, really) makes me want to just shut down at the end of the day.

It’s much better when you get to spend a significant part of your work week building new skills, or at least improving existing skills.

I was the technical director at a place where I was on one hand responsible for the dev team, and second highest paid person after the managing director. On the other hand I was also the person who'd lug new servers into our racks when needed. Part of the fun is being able to be all over the place and have a hand in every pie. Downside is the times when you don't have a choice because there's nobody else with the right skills.

The "promotion" to MAC (moves additions changes) technician was my first raise.

Please go to this client, take these monitors upstairs, and deploy them. We expect this to be your next few months.

For $4 an hour more than I was making as MSP sysadmin? Sounds awesome!

I was disappointed when that contract ran out.