How to specialize after a career as a generalist?
However, I am now in my 50s, and want to move out of my position (e.g. away from the organization I am at)... but it seems when I look around, there are very few "generalist" jobs in the IT field (that pay more than entry level). I am not making 6 figures, so not asking for a lot of money, but I can not live on "fresh out of college" pay.
How does one go about specializing when there are so many things that are interesting? I feel like IT is going through the same thing that happened to engineering and medicine... at one time the barber was a doctor. At one time a Physicist could do it all. I feel like I used to be that person in IT. You need a database, no problem. You need a webserver, no problem. You need some service stood up in the cloud, no problem. Now when I look at jobs, they want specialists, but I am the old jack of all trades.
How do you HN "old timers" who have chosen to move on and can not find the old general sysadmin position decide which field to go into? I mean, do you just wake up and say "I want to get back into programming and do full stack devops?" or "I want to go into networking" and spend thousands getting a CCIE? I am just not sure how to take the first step on the journey of a few thousand steps. I have done the "what interests me" games, but I find a lot of things interesting (probably one reason I went into sysadmin)...
I know this seems general, but any help would be appreciated.