My name is João. On paper, I was just another Canadian-born Portuguese guy. But on September 4, 2018, I became something else entirely when I boarded a Lisbon bus with a backpack, zero travel experience, and what might charitably be called a ‘plan’ to reach Ulaanbaatar overland. No flights. No itinerary. No idea what I was doing. (Picture Frodo offering to take the Ring to Mordor, but without Gandalf, the fellowship, or… you know, directions.)
What followed was the kind of education you only get by throwing yourself into the deep end of the world. I crossed borders in countries I’d only heard of during those doggy World Cup qualifiers (“Wait, that’s a real place?!”), slept in train stations where pointing at things was the primary language, and somehow became an ESL teacher in Asia – not through any particular talent, but through the magic of being a native English speaker who could stand upright and mostly avoid drooling in public.
When the pandemic hit, I developed a questionable talent for being in the exact wrong place at exactly the right time – always one step ahead of lockdowns, like some kind of reverse-Midas where everything I touched turned into a border closure. (This is not a skill I recommend cultivating.)
Now, after five years of beautiful misadventures, I’m here to share what happens when stubbornness meets poor planning. This isn’t another travel blog full of Instagram clichés – it’s about how to actually make travel sustainable. Like how to teach English abroad without losing your mind, how to work remotely without getting fired, and how to cross borders without (usually) getting detained.
Want the unglamorous truth about long-term travel? The kind where you’re not just passing through, but actually living in places where you don’t speak the language? Where bad days make good stories and good days make you wonder why anyone has a normal job? Let’s begin
To help you get started, here are a few questions:
One Long Solo 