So while you won't be able to play one game on the same account on two headsets at the same time, there's a pretty simple workaround so that you can still basically do that! I'll try to do my best to explain how it works here.
For the account that you currently have, it is considered the admin account on both headsets. For one headset, you don't need to change anything. For the other headset, you're going to want to create a second Meta account and add it as an additional account. Once you have both accounts on that headset, you will want to turn on App Sharing from the admin account on that "shared" headset.
So at this point, you should have both headsets on the same admin account, but one headset has an additional account with App Sharing enabled. In order to play the same game simultaneously, you just need to make sure you are using the additional account on the "shared" headset. Then you should be able to use the same game at the same time!
(Do note that some games may restrict online gaming for App Sharing/additional accounts. However, this is the best way that I've seen work for most cases like this. I hope it helps!)
BlueBerrieSmoothie provides a good response if you only have two users in the family. If you have more than two users you will not be able to play under your own account no matter what at this point as you can only share apps on one device under a single admin.
Example: Parent (admin) has two children. Parent installs a game on device 1, and a different game on device 2. Sharing is turned on for device 1. Child 1 uses their account on device 1 and can play under their account. Child 2 can NOT use device 2 under their account and can ONLY play as the parent on device 2 as sharing is not allowed.
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