Knowing that I bounce between these feelings was what made me leave my career in the first place. No two people are exactly the same, and I know that I have met many great people who love the stability of an engineering job (or any other career). The question for me has now become, "If I know that I like to move around all the time, how do I work?". My first answer to this question has been this travel blog. Although I do not make any money from this website, it allows me to do something that I feel is progressive.
When I first bought my GoPro I did it to encourage myself to do more adventurous things. The camera has been a new found passion of mine and has piqued my interest in editing videos, taking photos, and sharing my experiences through blogging. Now, almost daily I have conversations with other travelers who have found ways to work from the road. So far I have met a man who retired early and started renting motorcycles here, then started teaching boxing, organizing fights, and his wife works from fiverr, where you can sell your time in almost any form, from photo editing to writing blog content. I met a girl that started trading stocks at a young age and now uses it as a means for funding her travels. I met a guy who started a website with links to streaming movies/TV. And just today I met a German and Costa Rican that started an online casino using a point system.
None of these people are rich beyond words, but you can hardly expect to find those people sleeping in a dorm room with 10 other people, one of whom is puking, one watching a movie without headphones, etc... The point is that all of these people have found a way to live outside the "box". They have created something and they even do it while traveling! To me this is the only measure of success and chances are they will likely be exposed to more lucrative job offers than they would have received if they had taken a career based job.
So when our parents say follow your dreams, I think that it is almost like they are saying that you should find yourself. Maybe that is simply what our dreams are. We test our brain after a full new day of experiences and then run a few trials of life (sometimes we don't understand them) but when we wake up we feel we have a new found purpose for the day!