Kairi,
When? When the voice in your head tells you it's time to. Many have posted here that what drove them was the need to break free of the restrictions of 4 walls. Just dressing alone while still had a draw at times would seem to lack purpose. There became a need for a form of validation. To do things that the average GG would do. For some it starts with night time drives to which get added short walks. Day time drives may follow, things progressing until one day you park up on a retail park, pull up your big girl knickers a head into the shops.
The thing is, only you will know if there's a need for you to take any of those steps. It's not compulsory. If it's something you feel you need to do then you'll be the one to know when to do it. We can help with suggestions of the what where how's, you decide the when.