I am learning this pose. For me it is helpful to use cushions as a support. That way I do not have to come up the entire way, but I can develop a feeling how it is to come up.
Next step will be to take one cushion away and then the next..... It is also helpful to repeat this pose. To go down and to come up with the next breath is easier than to stop for a five breaths when the head rests on the cushion. Nevertheless the pose has progressed already. In the beginning I have not had the courage to go down. I also pulled my shoulders several times in the beginning, because I tried to come up with the help of my arms. The thighs and bandhas are supposed to do the job, not the shoulders. It will take some time till I will be able to master this pose.
To come up is my challenge in laghu vajrasana and urdhva dhanurasana (and again in life).