I did it for ~20 months, 2013-2015. I wandered about ~9-10 countries in Asia over that period. I mostly talk from the perspective of doing it internationally.

There are a lot of factors to go into to decide whether it's for you or not.

- The reasons why you do it: I am an Indian citizen, who cofounded a company in SF in 2012. I couldn't get a H1B visa (2 years in a row), so I worked on my company remotely until I could figure out an O1A visa. I did it because I can't get anything done at my parents' place in the Middle East, or with the shitty internet in India. I did it because it was the best among a few poor choices.

- What you hope to get out of it: I went in with few expectations, and so I enjoyed it a lot more than I thought I would. All I was looking for was good food and quality internet. I got a lot of cultural exposure, interesting people, and a realistic understanding of what's important in life. Don't expect much pleasure and excitement from it, and you will be amazed by what you can find.

- Your financials/work: I was making a below-poverty-line SF wage, but not living in SF. I had way more disposable income than I did living in the Bay. Traveling is suddenly way cheaper when you don't have to pay a home-rent, and you're making American wages in Asia. Never had to stress about money. Eating into savings to travel feels scary and makes you not want to leave your lodging. If you are a contractor/freelancer, this is way harder to do I believe, as you have to synchronize with people who don't know your lifestyle or work patterns well.

- Your citizenship: This makes a world of difference in how pleasant and stress-free the experience is. I had to spend multiple weeks in between every set of countries procuring visas from India to go to the places I wanted to go. I had to write off destinations just because of the hassle of getting visas and not because of time or money. If you're EU/UK/American/Australian/Singaporean/etc, you can enter most countries without ever needing to go home, allowing you to conveniently hop around at your leisure.

- Diet: If you have dietary restrictions, I would honestly think this shit is not worth it. Maybe I value food more than most people, but if it weren't for the varieties of interesting and new foods that I could eat without fear or care for the ingredients, my travels would have been so much more stressful and so much less interesting and fun.

- Base cultural flexibility: Have you lived in multiple cultures before? Know how to not lord your culture as superior over others? Can take time to understand the realities of another country before you pass judgment about their morals and values? This is for the sake of both you and whoever you meet along the way.

I could go on forever, but if you have specific questions feel free to contact me via info in my profile. Also have written some small essays here:

http://keerthik.github.io/essays/#nomadchronicles

Edit: Forgot to add my conclusion that, while I was right that it was decidedly better than my alternatives at the time, I grew incredibly lonely, tired and frustrated with the limitations of the lifestyle, despite the freedoms it unlocked. I grew a TON over that time, but it wasn't free. I highly recommend trying it out if you have the opportunity, for a year at least when you do, not because it's pleasant but for the growth.