@cory I think what
@WoodCutr is saying in his signature, and correct me if I'm misrepresenting you WoodCutr, is that tree work involves being comfortable doing things that can, and oftentimes will, cause us discomfort. If we were perfectly comfortable in the trees all of the time, we might put our guards down and fail to instinctively notice things that are dangerous. Having some semblance of fear at all times is immensely protective; it protects us, others and the tree and the property it is on from getting hurt. But too much fear is detrimental to our well-being and our ability to perform any duties we may have.
Therefore, I see his signature as a play on words because how can you be comfortable at being uncomfortable? It is a paradox and therefore meant to illustrate the importance of staying on one's feet in a manner that is graceful and shows confidence and doesnt negatively affect our quality of life. It doesn't preclude anyone from becoming more comfortable at their craft; in fact that's half of the paradox.
That's just my personal interpretation of what he has as a signature.