Ask HN: Should I specialize?

Hi Hackers, I have been programming a long time and I enjoy it alot. I don't get much free time these days and my job requires me to be a bit of a generalist across the .NET Stack, ASP.NET/SQL Server WCF,REST,and Javascript. With the lack of free time and work time being spent more recently on solving mundane business issues in a chaotic unorganised environment with not much good team work or good management for that matter. (I've already designed the application framework, delivered it, supported it a while, tried to spread the knowledge among the permanent staff.)

I am feeling like I am ready for a change of career at the moment and I am debating with myself about taking some well earned timeout to do some intensive educ-macat-ing and studying up in a specialist area of technology and maybe perhaps getting involved in some open source work, building relationships in the tech community and perhaps building a product or two to help with my learning. I need to decide what to specialize in, I have many interests that I would like to pursue ( .NET Mobile, BI, Javascript frameworks, SQL Server, Functional Programming,Node, NoSQL, Music ), but I think I need to focus in one area, perhaps becoming more expert in an area of the Microsoft stack or maybe throwing a curve ball and going for something completely leftfield.

I obviously have to keep a roof over my head and keep everyone fed and clothed, so I reckon I can afford perhaps 6 months to a year out of my security and just see where it takes me.

All suggestions most welcome!

Thanks. Shay