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I wouldn't necessarily consider you 'real dreams' out of reach. I mean they may be more difficult now, but not impossible. Clayton Christensen, who is a world renowned professor at Harvard, says 'I had been out of college and in the working world for years before I figured out that I could make it back to school to teach and develop a generation of wonderful young people'[1]. Now, most of us aren't Clayton Christensen level of awesome, but I think the general point stands. You CAN make drastic changes in your life, even if you have gone off 'into the weeds'. As for CV fears, in my experience, in the tech industry (assuming this is the target industry, I don't know much about others), your CV/pedigree is less important compared to what you know / can do. Demonstrating the latter can be harder without having the former as leverage to 'get your foot in the door', but having public depots of things you have worked on (ala GitHub), helping out on OSS projects, networking with people in the area via meetups/tech talks/etc... are all good ways to 'get your name out' so you can rely less on credentials to get opportunity. I can definitely relate to the being a loner thing, I am myself. I have had a number of friends/family pass away and it has made me very hesitant to make close friends because losing people that are close to you sucks. Participating in online forums/mailing lists in order to learn and help others can be a good way to get some 'socializing' without having to actually