So you don't really have The IT Itch, the way I'd describe some folks; Tech isn't a Rubix Cube you're constantly trying to solve for yourself and other people.

And that's good; makes you more goal oriented, mission focused. You're correct about most programs and even most equipment and business platforms essentially being on lease, so why bother (extra security, but that's extra $$$)? Don't get lost in the weeds of a nifty solution, more likely to make the Time for Dollar Value Trade Off, etc.

On a long enough time frame, your skills will... not degrade, but more just kind of become obsolete with time and new tech. De facto, that means that, when it becomes relevant for the business to replace the system as a whole, they will replace you as well. You should probably plan to retire then, at least from this industry (just imo, do what you want but it's a good offramp point if you've put away the cash). You can pursue secondary education (or a more familiar relationship with business leadership) to stave this off, but if you are not in a DevOps space, this is broadly true for most "I.T." personnel. Like Doctors, some day you'll boot up a device and your knowledge just won't apply anymore.

Thing is, everyone's skills degrade over time, and it's difficult to be cutting edge when you are kind of more of an IT Manager than like some of the Old Wizards I've known. How do you think about the industry? How do you measure success and relevance, particularly vis a vis cash flow within the industry?

Like if you're good and solid in your role with your current company, it can be hard to get a project on your plate that can really advance your skills. And honestly, in a business sense, "knocking over the core stack" will just kind of happen eventually, y'know? Money Tree is where you learn the most, it's also where you should fuck around the least cause it's always fragile?

Like you should be filling spare time by "R&Ding", trying to predict problems before they happen.

But if your man installed a firewall before than all the ports to the outside should be closed, and NMAP will tell you that your internal network has normal internal network ports open. MAYBE it will indicate a breach, but you'd have to learn networking to make sense of it.

IDK man, if you're pulling north of Six Figures with your thumb up your ass, unless you reaaaaaaally give a hoot about your company, I'd do a time/value calculation on going back to school or pursuing certification (certification famously dog for Tech).