There's something to be said about stepping outside your comfort zone. I do this best when I'm comfortable that my mistakes won't come under fire when/if they occur. Which is why I don't experiment when I'm shooting a big production for a paid client. Too risky on all levels.
When do I experiment? On my test shoots. I don't have nearly as much time as I used to, but I test as often as I can to keep my skills current and broaden my skill-sets. Testing allows me to balance my schedule, stay sharp, meet new people, feel the pulse of the industry, practice what I know, find out what I don't know, amongst other wonderful benefits.
I won't go into the specifics of what I tried because that's not the point of this post. The point is that like anyone else, I can fall into a rut and do the same thing over and over again. Fortunately I get bored quickly and usually try something new.
My model today was wonderfully accommodating which allowed me to comfortably be uncomfortable. Like coaxing a turtle out of its shell, I'll stick my neck out if I know the coast is clear.