Head over heels, or How I learned to stop worrying and do a (freestanding) handstand push-up
Disclaimer: doing handstands and handstand push-ups is difficult and potentially dangerous. The author is not responsible for your safety: you are. Please be careful.
On my very first visit to the CrossFit website, the "Workout of the Day" called for handstand push-ups. Now, I'd done some of these against a wall, and assumed that's what they meant. At least, until I saw this on their exercises page (which, incidentally, contains many other great exercises demo videos). Ever since then I've wanted to be able to do a freestanding handstand push-up.
The first step in learning to do a freestanding handstand push-up is, of course, to be able to do a handstand. This proved more difficult than I had anticipated. Usually, I don't do well with long-term projects; I lose interest or get frustrated when things don't come to me quickly. So I was quite proud when I stuck with this project even though it took me several months to get a solid handstand hold. I couldn't have done it without the tutorials at the fantastic Beast Skills website. To the tutorials there, I'd like to add a couple of things that helped me:
Use your shoulders. You can adjust your bodyweight forward and backwards using shoulder movements. This is very important for helping to keep your balance. I also find I use my arms to move up and down to adjust my balance if I'm losing the handstand, but most of the time you want your arms locked so you're not tiring yourself out too much.
Try kicking up from standing. I used the Beast Skills method of kicking up from a "sprint start" at first, but several people suggested kicking up from standing. At first I was very bad at this, and found it terrifying, but it quickly became more natural and controlled than the sprint start. Now I use something somewhere in between, which brings me to my next point.
Don't take the "kick up" too literally. One thing that helped me a lot was stopping trying to literally kick up, using a lot of momentum, but rather try to bring my leg up under control and then the other leg up to meet it.
Don't rely on the wall too much. This was one of my big mistakes: I stayed near a wall for far too long. One day, I realize that I had actually started subconsciously reaching for the wall with my leg when I kicked up. It was a tough habit to break, and if I had moved away from the wall earlier I would never have had the problem to begin with.
Force yourself to believe you will stay up. Now that I've gotten pretty good at holding the handstand once I'm up, my biggest problem is getting up to it. I still usually need to take a couple of tries before I can kick up properly. I no longer have "catastrophic" falls (thankfully!), but I do wish I could kick up more reliably. So, what I've started doing is saying to myself "you are going to get up and stay up no matter what" before each attempt. It works surprisingly well.
Once I got the handstand, the push-up came surprisingly easy. Part of this is because, as I was learning the handstand, I was doing handstand push-ups against the wall to build my strength. Against the wall I can do a set of 15-20 reps relatively easily. Balance is a bit of a concern, but it does come fairly naturally once you've learned to balance at the top of the stand.
Right now my personal best is 5 consecutive freestanding handstand push-ups. My goal is twenty. Then it's on to clapping hand-stand push-ups!