I work in IT. Currently as the IT Director for a medium sized company.
I kind of thing what you are asking is: "What was your path to success"
I used to be broke as hell. I rented a literal crack shack with a couple buddies while I was in collage. What it takes to succeed is time and effort. Being smart helps, but that is something you kind of get at birth. The rest all comes down to how hard you work, and how you stay the course.
I paid my way through university by joining the military reserves. My first tour (Syria) paid for my degree. My second tour (Afghanistan) got me a house down payment.
-The degree landed me a job working for the province of BC
-The work there allowed me to jump ship to IBM who was delivering a contract to the province of BC.
-The work at IBM got me into an investment management company.
-The work at the investment company got me into a defense contractor managing a fairly large portfolio, had Canada invested in defense I would still be working there.
-The title of partner that I had at the defense company got me my current position at a local company.
The point I want to may is that it is all sequential. Good things lead to other good things. So as much as you can, front load the work to get that first degree or good job. Once you have that on your CV people start to believe in you, because they can see that other people believed in you. So pick your path, start working hard, and think of the effort as laying a foundation.