Thanks, Henna, for your comment and the link. What a rich and beautifully written post. I wonder if your third point around scanning the environment might suggest an answer to your timing question here. Are there signs that present themselves that can be used confirm that the time is right? In the case of my son, his readiness has played out in countless ways large and small over the past year... it was obvious.  But sometimes it's more subtle... that feel of unease with what is, energy flowing toward or away from certain things. Maybe we need to scan our 'inner environments' for signs that the time is right to let go. And, getting it wrong either way (holding on a bit long or letting go a bit early) can be feedback to inform the process going forward.  Thanks again for sharing your post.  I look forward to learning more from you!