Whatever it is you're doing, make sure it's playful and fun. Don't push hard to get past the tough spots. Instead, just move gently around them.
With hand-standing, this means:
1. Don't rush headlong to be upside down!
Where you are right now is a good place to be. Begin in a cat-cow, gently rolling your hips around, and staying relaxed enough that the rest of your body just goes along for the ride.
2. Just move.
Now lift your hips into an easygoing down dog, with a nice bend in your elbows and knees. Keep rolling around, leaning your hips off to the left and right, allowing your legs and arms to move when and how they want to move.
3. Keep exploring, stay relaxed.
As you're rolling around, maybe inhale a leg up, opening up your hip, then exhale to relax it right back down. Same thing on the other side. You're not trying to get anywhere, you're just exploring how it feels to be where you are.
4. Connect your whole body with your breath.
Rather than just an isolated movement of your foot up in the air, get everything you've got working together. When you inhale, rock your weight forward into your hands as your thigh lifts and hip rolls open. As you exhale, relax everything you've got, down and back to the ground.
Two things will help here:
5. Relax on every exhale.
No matter what effort you exert on your inhales—like lifting a leg and leaning some more weight into your hands—on every exhale you're coming right back to relaxed and easily-movable in your body. This way you're always moving from easy, rather than from stiff and tense.
6. Keep your whole body easy.
Keep your arms, legs, and your whole body relaxed and easy through all of this. If you line everything up just right, then lock your arms and legs tight, you'll have not much choice but to launch yourself up in the air and hope for the best. If you do manage a balance, with your body rigid and tense, you'll have to make every little decision about what part of you to put where. It's tough to do much when you're making all those decisions! It will likely lead to headaches.
Keep your body—and your mind—relaxed. When you don't hold yourself tense and rigid, you can move everything you've got easily from your middle, and trust that your body will find its own way to do whatever it needs to do, in a way that makes sense for you.
This applies to more than just yoga poses!
It's great to practice this way. You're never stiff and tense trying hard to do hard things. You're just relaxed and easy, getting to know your body by moving and exploring. Do this enough, and hard things aren't hard any more. Plus, it's more fun!
Want to start moving and playing with your upside-down time? Here's a video with Tara to get you going.