He's in the fortunate position of being able to increase his job-market value, while actually working. If you really want to change your job, you might have to quit and start again from scratch - whether you are nervous or not.
Best advice I've heard is to make small changes that get you closer to your desired job, while utilizing your existing skillset, like asking for additional duties at your current employer. This way, you avoid the start-from-scratch phase you describe.
That's great advice. I took a position as a dev lead at my job a while back because I wanted more experience dealing with clients, budgets, estimating, and delegating tasks. It's been far more stressful than my previous position, and my pay has yet to increase accordingly (though it should within the next month), but I consider it a win for all the experience it has provided me. I look forward to applying these skills to my own projects.
