Well, it depends on how much money you want/need to make and how long you want your career to be. If you want to retire at 55 then it may not be worth it. It

Well, it depends on how much money you want/need to make and how long you want your career to be. If you want to retire at 55 then it may not be worth it. It may take you 5 years or longer to go beyond 'entry level' in an IT career. So you may (probably will) not make six figures during that time. Does making ~60k while you learn the ropes sound good? There is some age discrimination (less than people make out imo) in the IT/programming world, does that bother you? Does the idea of being on a team primarily of younger folks sound fun or terrible? :-) The company I consult for hired a new batch of HTML programmers (very entry level), many are college age and we had one guy who looks to be in his late fifties. shrug At 44, is your ego prepared to be constantly battered? If you do It/programming right, this never goes away, as you'll continually hit plateaus that are painful to overcome. Basically I'm trying to say that there's no 'yes/no' answer to 'are you too _______ (old/young/smart/etc) to become a professional ______ (programmer/It/security expert)'. It's all trade offs, and depending on which ones you are OK with making will influence your decision. I find programming incredibly rewarding, but I very much liken it to a difficult sport. How bad do you want it, and are you willing to endure the challenges of getting there?