Creating circumstances that allow you to do things you wouldn’t normally do is a great thing. People talk about their ‘comfort zones,’ but you can bring that with you. Your comfort zone doesn’t have to be stationary!
The actions themselves are rarely the foundation of your comfort. Usually it’s the feelings associated with those actions, or the people you do them with, or the cost to make them happen. But those are all things you can wrap around a new action if you set it up right.
You can bring a few friends along. You can combine the new thing with old things. You can establish safety nets. You can mix and match all sorts of circumstances to let you explore the great wide world.
You can also just jump off the deep end, but not everyone will do that. And better to wade in the shallow end first than to never do it at all.