Just do it
I have a friend who has a dream to leave his abusive job and do what he does self-employed.
He's really good at what he does and his clients have said they'd follow him whereever he went.
In my opinion, he has everything he needs to start (not just skills but other things like connections, etc), but he's apprehensive. Confidence, fear, timing, i don't know what it is. He really wants to do it but needs a kick in the pants.
If you've been down that road, and it worked for you, please, let him know how it went, if you'd do it again, what to do and not do it, what to look out for, etc. Or e-mail me, and I'll forward your message to him.
(By the way, he's agreed to this being posted here, he's not uncomfortable with it, he's looking forward to the response)