Reinventing myself slooooowly.

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I've done it once before. It took a year of persistent bullying, crying myself to sleep, thoughts of suicide, miserable months spent staring at my shoes and not speaking even when spoken to before I finally had enough and made the conscious decision to become someone else. I did it rather easily, to be honest, but over time I fell into a rut. I need to be that new person again. I need the drive to impress, I need the ability to put my terror into a compartment and file it away so I can jump into new situations and conversations with no shame or trepidation. My motivation is pretty sound. I'm an adult now, but I'm living like a kid. I dress like a kid. I put on weight. I look terrible, like some gross manchild who lives with his parents, watching cartoons in between classes and only coming out of his room for college and when mom calls for dinner. Because I am.
Some things are more important than others. Physical issues come first.

1. Get a haircut.
2. Lose 20 pounds.
3. Keep lifting weights and doing pushups. There's a lot of progress with this and the muscle is starting to look good.
4. Acquire new wardrobe.

The image is certainly part of it, but it's not enough to just look like I've at least graduated preschool. My maturity lies directly with severing my dependence on my parents.

1. Get a job.
2. Pay them back what I owe for the car they bought me.
3. Take charge of my education.

I also need to develop real relationships. No matter how much I pretend I'm happy to be alone, I'm not.

1. Convince some poor sap to overlook my flaws and take a liking to me.
2. Join a club, or SOMETHING. Do something that puts me in contact with other human beings doing something that I enjoy.

Also, I need to stop the self-sabotage. I've basically made an entire religion out of intentionally denying myself what I want and choosing the least enticing option. This is stupid and insane, regardless of how I may view it when I'm depressed.

This is a pretty standard checklist, but my motivation tends to wax and wane really quickly and a simple goal usually isn't so easily accomplished.
Wish me luck.

I will wish you will in the stead of luck. While I admire your ambition at the outset to improve yourself, (i sure as hell could use some of that drive), i think maybe are being to hard on yourself. It sounds a little like you are aspiring to a stereotypical ideal of self sufficiency. Perhaps consider this, and that everyone has their own path, it doesn't need to follow a formula. But if that shakes your confidence in anyway do what you need to do. Dont doubt yourself. Go forth and conquer!
That being said, do allow yourself a sense of humor, solemn concentration can be overbearing, and needs to take a break now and then. Do have unwavering faith in yourself, but taking yourself too seriously could definitely backfire.

I need a haircut pretty bad. I cut my own hair so I'll probably do it within a month or two.

20 pounds won't help me much. I used to ride my bicycle between 3,000 and 5,000 miles a year but had to quit because of carpal tunnel causing too much pain in my wrists and hands. Since then, I've gained about 80 pounds.

I'm quite happy with my wardrobe. Cheap t-shirts, cheap shorts, and cheap socks work fine for me.

Wishing you luck, Dent.

And crossing my fingers for you that all goes the way you wish.

Edit, since I read another thread and felt a bit self-conscious about this: I went out for my haircut that I've been putting off, spent 4 hours driving around, visited 3 different cities in my search, and utterly failed to accomplish anything except waste gas.
My inability to function like a regular person astounds me.

Sweet Pea hugs

I hope your reinvention turns out.