I spent about three years supporting myself abroad, mostly badly, through a series of jobs that are all presented online as easy ways to fund a life of travel.
They are not easy and several of them are worth doing anyway. Here is what they were actually like.
Hostel work
The most common arrangement. Reception, cleaning or bar work in exchange for a bed and sometimes a small wage.
What it is actually like: early starts, split shifts, cleaning that is genuinely unpleasant, and living in the place you work, which means never being off duty.
What it is good for: it is the fastest way to know a place and to meet people, and the other staff become a social circle immediately. Several of my closest friendships came from three months of this.
The economics are poor. A bed plus a small amount is below any reasonable hourly rate. What it buys is time in a place at very low cash cost, which is a different thing from earning.
Teaching
The most reliable income of anything I did, and the most demanding.
Requirements vary enormously by country. Some require a degree and a certificate and a visa arranged before arrival. Some require considerably less and pay accordingly.
The work is real work. Lesson planning takes time nobody counts, classes of children are exhausting, and being bad at it is obvious to everyone including you.
The people who do well at it are the ones who treat it as a job rather than as a means of funding a stay, and they generally stay for years rather than months.
Where it is genuinely good: it produces a routine, a workplace, colleagues, and a reason to learn the language, all of which are what actually make living somewhere different from visiting it.
Seasonal work
Agricultural work, ski seasons, summer resorts.
Physically hard, particularly the agricultural version, which is harder than almost anybody expects. Long days, piece rates that reward experience you do not have, and accommodation that is frequently poor and deducted from your pay.
Ski and resort work is better paid and comes with something worth having attached, which is why it is competitive and why the good positions go early.
The critical thing with any of it is checking the visa position properly. Working holiday arrangements exist between many countries and have age limits and conditions, and working outside them is a genuinely serious matter with consequences for future travel.
Remote work
What I ended up doing and what most people should aim for if they can.
It is not a job type, it is a way of holding a job you already have or could get. Which means the useful preparation happens before you leave rather than after.
The practical difficulties are underdiscussed. Time zones, which turn a normal job into unsociable hours depending on direction. Reliable connectivity, which is not guaranteed and which is your responsibility. And the visa position, which for most countries technically does not permit working on a tourist entry regardless of where the employer is.
A growing number of countries offer specific arrangements for this now, with income requirements and application processes, and they resolve the legal question properly.
What did not work
Anything promising income from content about travelling. I tried, as everybody does. The number of people making a living this way is very small and the number attempting it is enormous, and I was not in the small group.
Casual work found on arrival, which was unreliable, occasionally unpaid, and left me with no recourse.
And relying on savings running down while assuming something would turn up, which is the specific failure that ended my third year.
What I would tell someone
Arrange the income before arriving, not after. Everything is harder from a hostel with a diminishing balance.
Check the visa position properly, from the official source rather than from a forum. The consequences of getting it wrong are disproportionate to any saving.
Stay longer in fewer places. Every move costs money and resets whatever you had built.
Keep a genuine reserve for a flight home, untouched. Not having one changes every decision you make and rarely for the better.
And be honest about which of these you are doing. Funding a stay and building a life are different projects, and the jobs that are good for one are frequently poor for the other.
What it does to how you see places
The part that is genuinely valuable and is hard to describe.
Working somewhere gives you a completely different relationship with it. You learn the transport, the shops, the way people talk to each other at work, what things cost when you are earning in the local currency rather than converting.
You also see the parts nobody visits, because that is where staff live and where the cheap food is.
Three months working in a place taught me more about it than a dozen two-week trips elsewhere. That is the return, and it is not financial, which is worth being clear about when the arithmetic is otherwise not favourable.