I applaud your optimism, I really do. Just don't go thinking you failed in life when you inevitability find yourself eating chicken nuggets at Disneyland for the third year running, whilst your children (that you love dearly) insist on yet another Disney Princess dress. :)
I have traveled this way since 1983, and I can remember showing up in Indonesia with my two kids, who were less than 10 at the time, without a room at 11 PM and walking around throughout the night until we found a great place to stay. I had just bought them their backpacks that year. Years on I lived with my newborn baby, my third child, in a rice-farming village in East Java for a year, and after a few months, I felt I was back in Brooklyn by identifying with the similarities of the situation and personalities of my neighbors. Travel changes your perspective both in immediate, new ways, and in long, introspective stretches. I recommend it if there is an itch you feel you need to scratch. I have never regretted any of it. I had already traveled a lot of SE Asia when I saw The Beach, and I liked it, especially the contrast between the new arrival and the has-beens of backpacking. The Jungle (2017) is another film worth watching based upon the true story of Yossi Ghinsberg and his ordeal in the Amazon rainforest in Bolivia back in the 1980s.
It's far from _inevitable_. As the GP writes, it is the spirit and openness of the journey that is important and this can work for families and older people. Of course you adapt to suit your party.
When backpacking with kids, we only relocate every week or two, not every few days. We have rest days for schoolwork. When cycle touring, we don't go more than 50km in a day. We eat a lot more icecream. But it is still unplanned, unscheduled and intimate.
