Okay, so the first thing I did to challenge myself was to really step out of my comfort zone by undertaking a fine art nude workshop (Yeah, I never thought I'd ever feel comfortable with being around a naked model let alone take pictures of her... but it's so easy to forget she's not wearing any clothes when you get into the photographers mindset).
If I didn't take a chance I wouldn't have found such a fantastic local studio with such a great group of people who hold weekly workshops (not all of them nudes :P), and I wouldn't have known that I can work with a model in the most awkward of conditions.
So what I've learnt is that: You need to step out of your comfort zone to add some excitement and challenge to your life.
How have you stepped out of your comfort zone? Have you been in any awkward situations before?