Depending on how long and where you plan to be, you’ll occasionally risk running afoul of rules about working remotely while in tourist visas in foreign countries. These are weird and annoying laws, and can cause real problems, from fines to deportation to getting a restriction (ban) on your passport. Definitely get clear on what level of defiance you’re comfortable with, and what manner of hoop jumping you’re motivated for should you, for example, want to live in a van in the Schengen, the UK, or Canada (idk where you’re from but this is aggro in the usa also if you’re a non resident) for an extended period while working for a company and drawing a salary in your home country. I’ve done small scale freelance work for companies based in places I have legal right to work while residing in vans in places where I do not have such rights, but it’s largely been under the table, and it would be tricky to piece enough of that together to live securely. As for working locally for cash under the table in foreign countries, it’s a tough balance. Most countries where are you could maybe justify take a job that would otherwise be performed by a local person (cleaning a refugio for example) are going to pay a local salary, and this isn’t going to be adequate if you plan to spend your time climbing. It’s also just kind of questionable to be from a rich nation, go to a poorer nation, and start working an unskilled job. Maybe this happens? I’ve not seen it much. In rich countries, assuming that you have the language skills and community connections to find work under the table in a foreign country where you don’t have the right to work, well…the thing is those factors are hard to line up, and most rich countries are not like the US, where the culture of working for cash is much more common. In western Europe for example, most average people are simply not comfortable hiring a foreign person under the table to set routes at a gym or serve pizza. So it really depends on the algebra of your particular needs, your resources, and your tolerance for ignoring immigration laws and the needs of local populations. On the other hand, if you already have a real job you can do from anywhere, Iceland has a special one year residence permit for remote “digital” workers who earn minimum of 80k€/year (I think), but it’s unusual and wouldn’t give you freedom of movement beyond what your nationality entitles you to (90/180 in other schengen countries, 6 months in the uk if your American or Canadian for example).