Caley Alyssa is an L.A.-based yoga instructor and the founder of Caley Yoga. Her new class, Yoga Inversions 101: An Introduction To Getting Upside Down gives you a step-by-step approach to nailing handstands, headstands, arm balances, and more.
Most of us yogis believe that headstands are "easier" than handstands. And in some ways, they are. You have more of your body on the floor (head and forearms) than you do with a handstand, which makes you more stable. In most cases that means you can stay up there longer, which is a nice feeling when you're a beginner.
There are some experienced teachers, like Dharma Mittra, who believe that the headstand is the king of all the poses. One of its many benefits is that it may actually stop the aging process.
While the idea of staying 31 forever sounds enticing, and as I love doing headstands myself, they can be extremely dangerous for new students to attempt. A headstand puts most of the body's weight on the head and neck. This means that if you somehow manage to fall out of the inversion, you're risking a very serious injury.
So, instead of teaching newer students headstand as their first inversion, I prefer to teach them handstands. Handstands are much easier to eject out of when need be. You can cartwheel out, step out, spin out— the point being, your neck and head are less likely to get injured if you fall.
I am by no means implying that you should never do a headstand! I'm just saying you should begin with handstands.
Once you get the feeling of having your legs over your head and finding balance there, then you can move on to your headstands. You don't have to be able to hold a handstand, but you should be able to practice them enough to become comfortable with the elements of the inversion. Then, you can headstand away.
Part by part, piece by piece, you will get there.