He didn't fly in the military because he joined right out of HS. Mil pilots slots are very competitive, involve a lengthy selection process and require college. You can't just "decide to do it".
The airline business involves dues paying because the potential end game is $300K+, more than half the month off, and a flexible lifestyle. Oh, and you get to fly jets.
IT will pay more out of the gate, but it will never approach the top airline payscales (which are reached by seniority, as opposed to politics, job hopping, and ladder climbing).
So you have to decide if some early risk and dues paying is worth the potential long-term payoff. If you're physically qualified, it would be worth applying for air national guard pilot slots after you get your degree...that will help to fast-track your airline career.