Instead of taking time off to do this, I'm doing it on the fly while my startup is up and running. I fought this fight for just about 2 years, outsourcing much of our web development during that time. And I don't regret outsourcing - it can get you up and running faster than learning, especially if you're building something that borders on complex. But in the end, we really needed to start bringing things in-house, from both the standpoints of protecting our IP as well as enabling us to become more nimble in terms of making changes on the fly etc.

We haven't completely weened off outsourced web development, but I can now see a path to get there, and it all started by learning how to become more self-sufficient.