Compassionate Demand: Pushing your boundaries and enjoying it

This post has been updated and re-posted from an earlier version.
One night in class I brought up this idea of being a combination of demanding and compassionate with yourself when learning something new. If you want to become an excellent practitioner of something (and that is a worthy goal), then you are going to need to call on yourself to do something you can't yet do and keep asking for the yet-unreachable again and again.
When embarking on a program to train myself to do 100 pushups in one minute I found myself facing some training days with goals that were absolutely beyond my reach. These could have been completely demoralizing for me but instead I chose to find them enjoyable and even kind of funny. There's something sadistically humorous about feeling completely exhausted, having just finished 75 pushups over 4 sets, and having a little iPhone program tell you its time to do another 25. You know when you set out onto pushup 5, and your arms are wiggling like Jello, that you're not even going to make it half way.
Yet its super important, if I'm ever going to make it past that 25 in the future, that I do every damn pushup I can till I fall on my face. I want my body to give up, not my mind. So I set out onto pushup 6, and then pushup 7 grunting like a man in pain. Then a quarter of the way through pushup 8 I completely collapse and immediately erupt into laughter. It's amusing how tough this program is and that I'm enjoying it none the less. The goal being as daunting as it is seems almost ridiculous but I'm in it for the journey AND the destination. I'm compassionate with myself and I'm not in a hurry. That gives me room to make demands on myself that I know I have to work toward, keep asking for. It also allows me to savour the fact that I can barely lift my arms over my head to change my shirt 5 minutes later.
So set far-reaching goals and then enjoy every little step. In your posture ask yourself to go deeper, lunge longer, extend further, make one more cut. Work within your limits but also push the boundaries, then enjoy the process and be compassionate the whole way along.
Devon