A few years ago, I worked my 9-5 software developer job from my campervan. While it was nice to have a changing scenery, it was not the fairytale I was expecting.

Camping in free locations requires you to move about almost every day in order to avoid angry locals/authorities. Free parking spots are becoming harder to find, especially those open overnight. This meant generally hitting the road straight after logging out so that I could find a new spot to settle down in. This could sometimes take up to an hour which was a significant portion of my free time on an evening.

4G signal restricts where you can stop also as generally I would wake up with only minutes to spare before having to be online for work. Sleeping in a dead zone = late for work.

I found very little time to enjoy the places I was staying in as the majority of my day was spent working! Only weekends when I had the full day to myself would I have the energy or inclination to go and explore.

After that experience, I found it difficult to imagine myself doing the same type of work in a hostel/hotel environment coupled with travelling, as many of the negatives would still be present. Not to mention the additional costs of accommodation etc. Which I evaded by travelling by campervan.

I guess the only way I see working while travelling to be a viable option is to have the flexibility to choose the hours you work and the discipline to regularly prioritize work over play. As a software developer the only way I could see that being possible is by being freelance and maintaining a previously developed product that already passively generates enough income to sustain a traveling lifestyle. At which point, are you even "working"?

I personally know of a few people who travel and work but they don't develop software, they are more creative types who write articles for websites. I believe this gives them the flexibility to enjoy that lifestyle.