This is a question I get asked all the time.
“How do you choose a place to go?”
People expect a practical answer. Some checklist, best towns for remote work, or like someone I met recently does — a spreadsheet comparing rent, WiFi speeds, weather and 10 other factors.
The practical stuff matters. But it’s not where I start.
After 5 years of moving every few months, the destination matters less than the lifestyle it can offer does. So, this is what I do:
I start with a feeling.
And the feeling is usually one of the two.
Sometimes I’m mentally exhausted. Too much change, too many decisions, too many things to figure out. In those moments, I don’t want novelty. I want familiarity. I want a place where I don’t have to build a life from scratch again.
That’s why I chose Bir in March. I was hosting my first slow living experience — a nerve-wracking bet. I didn’t want to figure out a brand new town and run my first group at the same time. I wanted familiar ground. Bir was it.
Other times, something inside me becomes restless and I want to be a beginner again. I want to land in a place where I know absolutely nothing. Where buying milk becomes an adventure for the first week. Those first few weeks, when every walk teaches you something new about a place, give me a kick unlike anything else.
In those phases, familiarity starts feeling limiting. I need a place that stretches me.
Knowing which mode I’m in is the most important decision. The practical stuff comes after.
Once I know which mode I'm in, I focus on the handful of things that shape how a month somewhere goes.
This is the easiest one. If I can’t work, I can’t stay. Reliable internet is non-negotiable.
Can I walk here, or will I need a vehicle every day? The more walkable a place, the happier I am. I notice things more and feel like I live there instead of just visiting.
I plan my movement around escaping extreme summers and harsh winters. My body works better in certain climates.
It has to make sense financially because I want to stay for long. A place that stretches my budget also shortens my stay. And time, more than anything else, is what creates belonging.
This is the hardest one to predict. And the one that often decides whether I’ll stay longer.
Are there people I can imagine becoming friends with? Workshops? Creative communities? Interesting locals?
Beautiful places become lonely very quickly without good people.
Do you notice what’s not on the list?
The “Top 10 Things To Do.” Tourist attractions. Instagram spots. Those matter when you’re visiting, not when you’re living. When you stay somewhere for a month, your life becomes ordinary. You’re buying vegetables, doing laundry, cooking, wondering if your neighbour's dog is ever going to stop barking. The extraordinary moments happen in between those ordinary days.
What’s funny though is that a place can tick every box on paper and still feel completely wrong. And sometimes a place looks average in every practical sense but feels surprisingly right.
That’s because the checklist can only do so much. It’s your gut that makes a decision. The feeling comes first. The checklist only validates it.
That’s why I find it difficult to recommend places when people ask,
“Where should I go?”
Because I don’t think there’s a universally perfect destination.
I think there are places that meet you exactly where you are in life.
Bir met me when I needed direction and then again when I needed expansion. Leh met me when I needed solitude and healing. Other places have challenged me, surprised me, or simply taught me something about myself that I couldn’t have learnt anywhere else.
I think that’s what we’re really choosing when we move somewhere new. The person we want to become while we’re there.
Next week, I'll answer another question I get all the time:
Spoiler: it never starts with Airbnb.
If you have any questions, drop a comment or reply to this email.
See you next week,
Love,
K
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.