Do you worry about coming out of the other end of these travels - by choice or circumstance - and not having the stability/financial cushion that maintaining a steady job would have afforded you?
No.
I've made a conscious decision not to live life in fear, and not make decisions based on fear.
Having spent 2 years driving from AK to Argentina and now 2 years in Africa, I know more strongly than ever that I'm not interested in a "stable" or "guaranteed" future. It takes away so much spontaneity and adventure from life, and those are things I'm not willing to give up. Without them, I personally don't think life is worth living.
Interestingly I have recently met a bunch of people in Mozambique/Zimbabwe/Zambia who went to university or otherwise lived in London/USA/Australia for a few years. As soon as possible they returned to live in Africa. Quote "I don't want to just exist, I want to live."
Just the other week I met a 92 y/o lady who knows all about adventure. In 1950 her Dad loaded his wife, two daughters and the family dog into an old truck and drove from London to Zambia. The adventures they had on that journey far outweigh anything I have seen or experienced. He randomly made his home there, and she had endless stories of sitting on the porch watching elephants and a million other things. In her lifetime she hand raised a hippo that lived in her house for 19 years, raised a chimp that slept in her bed, and now runs an orphanage/foundation for well over 100 chimps.
When we're open to it, we can find a life of adventure that is extremely fulfilling, and I want that life.
Could be. But also talking about all these other hypothetical adventurous people who are now broke and starving feed into our fears. I wonder if it just feels right to assume most people regret such decision because it matches what we worry about.
No. I'm not aware of anyone doing a randomized controlled trial on going adventuring. I'm just pointing out that people who died naturally won't be able to tell their stories, so we're disproportionately likely to hear from the ones for whom it worked out ok.
For one person choosing adventure there must be at least ten watching him/her closely succeed/fail so in our current superconnected world I would assume not so happy stories are still preserved somewhere.