How do you get over the initial fear?

so, I think I've basically mostly decided that by the start of the new year, I'm going to pack as much essential things/gear as possible (not entirely sure what those are yet)

I guess I've been thinking of how society usually fears or yells at vagabonds for not conforming to their standards, and eventually that got me thinking of how one would even transition from the "normal" life to a Vagabond lifestyle successfully. I presume there's a lot of fear behind such a massive decision and you'd have to adjust your mindset to become stronger than it was before after a life of complatency.

Any random advice for up-and-coming Vagabond partakers?