[shepbook]

I may be echoing others, but I to say to go for it.

As for the "gap", this is simple. Start a business. If you're going to be making and selling mobile apps, you'll want a basic corporate entity behind you anyways. Now, instead of being "unemployed guy building apps" you're "Founder of Mobile App Development Consultancy" or something along those lines.

Given what you stated about not liking the corporate world, that's completely understandable. I certainly prefer smaller companies, even startup, bootstrapping level ones. J2EE and .NET aren't strongly used outside of the big enterprise-y corporate world. Given your experience with Java, I'd say you might find Clojure to be a great move and still be able to leverage your Java past.

Go for it! Get yourself an LLC or similar and build some apps. If you have 5+ years of financial runway, you should certainly be able to find something self-sustaining in that time. :)

Jump and don't look back!

[skurry]

That's exactly what I'm already working on. I have a domain name secured, an app in the Android app store, and if I do make the jump, I'll change my LinkedIn to "Founder, <company name> LLC" or something like that.

I could use my C# skills to port the app to WP7/8, and I might even buy my first Apple computer and learn Objective C. Exciting prospects!

[tutufan]

No advice as to whether you should do it, but if you do, stuff like this will be useful to cast your adventure as "legit" if you want to return to the standard world later. I'd definitely work on leaving a trail/portfolio of your work as you go.