I've also tried free lancing but I've had the same kind of problems. I got a freelance job to build a property database for a local realtor. I managed to get started on the project but quickly got overwhelmed. After feeling overwhelmed I never touched the code again and felt too nervous to email the client back. This has happened a couple of times before with freelancing.
I've been for a psychological assesement and was told I had no problems. The doctor I spoke to suggested maybe I just wasn't suited to employment in a company and maybe I should start my own thing. That's what I decided to do.
I had an idea that I'd like to develop and managed to make a very simple prototype. I invested all my savings in the company but now feel like I'm under so much pressure from myself that I can't do anything. The day I set up the company I spent the entire day in bed because I felt like I couldn't face doing anything.
I feel like I've tried everything. All sorts of to do lists, books on procrastination, exercise, keeping myself accountable to other people and so on. I just can't seem to get started doing anything, and when I do it feels so painful that I can't continue. Occasionally, maybe once every 3 months or so, I'll have a day where I get lots done and I'm really focused, but I've never been able to work out how these days are different from any other day. I always go to bed feeling great at what I've achieved and then wake up to another day of nothing.
I'm going to visit a doctor again next month, but I wondered if hacker news could offer any insight on the situation. Is there anyone else who had a disastrous level of procrastination who has managed to turn it around?