The answer to both questions is the same: In order to live a life that is epic and exactly as you want it, no matter what that looks like, you basically have to not give a fuck about what anyone has to say or thinks about how you live your life. At the end of the day, you are the one who has to be happy with yourself.
A lot of it comes down to changing priorities to travel above (almost) all else: Just do it and don't be sorry about it, at all, ever. If someone wants to gaze down because they have a different standard of living, that's their problem. Why? Because your life will be awesome and exactly as you want it. Everything else falls into place.
As an example, I'll use my "Buying legal weed in Colorado with a North Carolina" ID post. I got some comments on Twitter practically condemning me for doing the piece because, according to their beliefs, marijuana is a gateway drug - regardless of the fact that anyone who's ever been around it knows that it's not. If people are going to get addicted, they're going to get addicted, MJ or not. I'm a travel writer and I just happened to be in a state where a noteworthy event happened - so I wrote about it. This is part of the gig that is also my life. Was I able to sleep that night? Absolutely. Was I sorry at all? NOPE.
People are entitled to their opinions, and aspiring nomads need to know that they are, too. It seems so simple, but people complicate it with excuses. Perhaps it's the human condition. If you want to be a nomad/travel writer/pilot/live on a boat/go off the grid/whatever, do what you've got to do because at the end of every day, you're the only one that can make a happier, less lonely, or perhaps more traveled life.