I’ve been working on flying pigeon for a while and still have a fear of falling on my face.
I was doing a non DYWM class on the weekend and they suggested using a block to practice to get in to the position with leg extended - so you put the large surface of the block down in front of you and lean forward to place your forhead/top of the head on it while extending the leg. I had been using pillows before that and really didn’t feel like it was very effective, but using the block like this was really helpful to me and I could extend the leg and feel safe doing so. In being able to safely try this pose without fear of face planting, it also made me realize that I am most definately not able to do this pose on the left yet because I don’t have the hip flexability - my knee kept slipping off my arm on that side - and I had been wondering for a while if this was the main problem or not, but using the block with this position made me realize that it definately is.
Hope this may be helpful to anyone else struggling with this pose.