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 socialize :) Then the next step would be dreaded socializing IRL, but that is less scary once you have established some kind of reputation, even if it is just 'that guy that answers questions on technology X on (mailing lists/StackOverflow/Other)'. Don't spend too much time worrying about other people or if they view you as a failure or whatnot. People that make those kind of sweeping judgments on others are, more often than not, worthless people to know/interact with.

If your concerns are interviewing just realize it is a skill like any other. No one is really 'born good' at it. I think people that think they are either have interviewed only a few times and happened to get questions they already knew or areas they were very familiar with, have interviewed a lot and thus have a lot of practice, or they are just trying to appear awesome by acting like interviews are just a cakewalk for them. Most people get nervous at interviews, especially since you are basically competing for a job, which can be stress inducing. I don't know if there are tricks to getting better other than reading some of the better books on interview prep and practicing. I know some schools have mock interviews you can participate in (possibly only for alumni/current students) to get practice so you are less nervous. One other thing to keep in mind is most of the time the interview is not to see if you know the correct answer, or even if you can come up with it under a time/pressure deadline. Rather it is to see how you approach a problem, what kinds of questions you ask, how well you can verbalize your approach. Most interviewers will try and steer you towards the right answer if you are asking questions or 'throwing ideas out there', unless they suck at interviewing, in which case they just sit there mute while you wander around the answer space. Sucky interviewers suck, but you will likely encounter a few.

20120910 gives good advice, and he is honest that you may encounter a lot of depressing events (rejections, failures, etc..), but everyone does (okay, most everyone, some are born silver spoon firmly affixed in mouth). The important thing is learning from them, relentlessly improving and continuing on. Not to sound too 'self-helpy', but really the only one that can hold you back is yourself. There are lots of oppurtunities out there, finding them can be a challenge, but the reward is great. It is also a great feeling to know that you have done it yourself and things weren't handed to you. I watched an interview with Chris Sacca the other day[2] and he had a hilarious bit where he was talking about the entitlement of some of the straight out of college hires at Google who had never had much adversity in their life, how they were honestly getting pissed off because the cafeteria ran out of pheasant one day (obviously an exaggeration, but I have met people that would view that as a major problem in their life). Just know, you aren't the guy complaining about lack of pheasant :)

[1] How Will You Measure Your Life - Clayton Christensen (http://www.amazon.com/How-Will-Measure-Your-Life/dp/00621024...)

[2] http://www.youtube.com/watch?v=Q6NpHbMFaQ8