I make it a point to, at least once per month, do something that appeals to me but seems too daunting, intimidating, or uncomfortable to do. There's no magic here. It's just an application of will.
For me, an important part of this is that I give myself permission in advance to fail or bail without shame. Working outside of your comfort zone means that you're taking a risk. Take the emotional cost of "failure" out of the equation by recognizing that the value is in the doing, not in the end results.