It sounds like you have self confidence issues which lead to a fear of failure. The only way to overcome it is to take a leap of faith. The time is now. I waited until I was 30 to really get over it, and I wasted most of my 20s. So basically:

- stop comparing yourself to others - stop being afraid of failure - just fucking do it

You'll be amazed how freeing it is to not worry about failing anymore. This isn't to say it isn't a hard "habit" to break. I still have my own doubts, but I just remember rejection/failure is only temporary. To paraphrase someone much wiser than me:

"On my deathbed, I will regret not trying things far more than I'll regret failing at them"

So my suggestion to you: start a side project and get to hacking. Pick a small problem that drives you crazy and set out to program a solution in Rails. It doesn't even have to be something to make money; you just need to put yourself out there.

Maybe this isn't you, but your story sounds very familiar. I've been self-employed since I was 20, but I never let myself take it to the next level. If I can save you or someone else those wasted years, it was worth writing this. This Steve Jobs quote still gives me chills, and it spurred me to change my life:

"For the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something…almost everything – all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose."