I'm happy for you.
I have a friend in a similar situation to you (in terms of travelling/freedom/finances). It doesn't inspire me to "find a better job". Frankly, it makes me suicidal (I don't mean that in a hyperbole way). I look at how successful he is and I think; I could never be that successful. He will be cavorting around the world carefree for the rest of his life, and I will chained to a cube (whether at this job or another, doesn't really matter) until I'm unemployable and on the streets.
Getting a better job is nothing like what you and people like my friend have. You guys are in such a different realm, and although I enjoy following along with his adventures, it also hurts when he (and I hear a bit of this in your post too) can't understand that most of us will never and could never be in that position. 90% of new businesses fail. I barely have enough savings to last a month if I was out of a job, so the risk of trying to start and grow a business is much more likely to put me into poverty than it is to put me into financial freedom.
When I encounter a service worker, such a waiter, customs official, bus driver, etc who seems rude and snappy, I try (this is hard for me) to think about what they might be feeling. They could be having a bad day. Maybe someone yelled at them. Maybe their boss is cruel and belittling, but they can't find another job. Maybe their kids or spouse is trouble. Maybe the table before me left a religious tract instead of a monetary tip.
I realize your post is tongue-in-cheek, and intended to be funny (and it is). But it's also a bit hurtful. I can imagine that exchange, and the customs official is completely demoralized. The question in your hypothetical dialogue are entirely legitimate: they need to know where you've been and what you're up to. Your responses, although accurate, are made in such a way as to say "I'm better than you." I know you don't mean it that way. The same as I have to spend time away from facebook just because the endless stream of travels of my friend depress me too much, I sometimes just need to not know about them.
I don't know if you've ever actually said that dialogue to a customs person, but I only request you think carefully. A lot of people struggle with self-deprecation and/or depression. And an exchange which it makes so clear that he/she/me are stuck trying to pay the bills and work two jobs while other people are free and have it all just drives the depression that much deeper.
I don't say you should give up anything, or that you didn't work hard. I'm sure you deserve everything you have! Please just don't rub it in the face of a stranger who is lower class than you :(