Been in IT for 22 years...started as desktop tech, then to help desk dispatcher, then help desk analyst, then help desk sr. analyst, then to network administration, then to server engineer/architect, then to large-scale IP network architect specializing in Cisco, then to SMS (desktop app deployment), then to application packaging and now I'm a configuration manager for a small company that sells a butt-load of software.
No college...in fact quit HS and had to go back to get my diploma to get the help desk analyst role.
Currently, the real money is in .NET programming, and cloud integration will be the next really long-term job skill. 6 figures is plenty easy with either of those if you're competent. A C# programmer with a good resume can pretty much name their price at this point, as can a cloud developer/architect.
Most smaller companies now don't even host their own source code or email, so a lot of the systems management functions are starting to be virtualized and moved to the cloud.
If I could do it all over, I'd have stayed in school and become a lawyer. At least that job is consistent and won't go away an time soon. Playing catchup with each new technology is getting old for an old fart like me.
That being said, even though it's been difficult and we've had to sacrifice, my wife has been home with the kids for 14 years. And, I've managed to be working for all that time with the exception of a 6 month period during the last recession. The key is to poke your head up once in a while and see what the next big thing will be and make yourself valuable by being good at saving a company money. 99% of the time, most solutions can be found by getting educated in a new technology...especially open source stuff...and not throwing money at a problem.
AJ