Hey,
A few months ago, I asked people a simple question:
“What’s stopping you from taking a work trip?”
274 people answered.
I expected the biggest problems would be logistics and budget. Budget came up, of course. But what surprised me was that almost every answer, in one way or another, was about fear.
Here’s a little of what they said:
“I may feel lonely.”
“I’m scared about safety in a new place, especially when I don’t know the language.”
“Will I be able to balance work and travel?”
“What if bad WiFi affects my work?”
“I might not find my rhythm.”
“Being too busy with work all week and not being able to take in the experience.”
“Safety, boredom, loneliness”
And then this one, which has stayed with me:
“That slowing down will make me uncomfortable. Because stillness leaves space for thoughts I usually outrun.”
It told me that the thing standing between people and their first work trip is not a practical problem. Wifi can be solved. Flights can be booked. The real blockers are working subconsciously - the fear of being lonely, of losing your rhythm, of not being good enough at your job from a distance, of what you might feel when you finally slow down.
You can’t Google your way past those. But you can be walked through them by someone who’s felt every single one and gone anyway.
I've spent the last five years working from mountain towns, beaches, cities, cafes, hostels, Airbnbs, and more homes than I can count.
People often assume that the biggest challenge is finding houses, figuring out WiFi, or choosing destinations.
Not really. Those things are easy. The hard part is saying yes before you know exactly how it’ll work out.
You don’t know if you’ll like the place, if you’ll make friends, whether you’ll be productive, whether you’ll find good food, if you’ll want to go home after three days.
Every work trip begins with uncertainty. And because our brains hate uncertainty, they disguise it as practical questions.
When I took my first work trip, I had every one of these fears too.
Some of those fears did come true. There were lonely days, trouble finding food I liked, and sometimes it was too hard to focus on work because the outside life was so new and interesting.
I did lose productivity for the first couple of days whenever I moved somewhere new. And yet, I kept doing it. Because every work trip taught me something I couldn’t have learnt by staying home. Eventually, the fear became smaller than curiosity.
Reading all 274 responses made me realise that people don’t need more inspiration. There are already enough Instagram reels telling you to quit your job and work from Bali. They already know working remotely from somewhere beautiful is possible.
What they need is someone to help them navigate the questions that come after inspiration.
How do I stay safe? How do I find a place? How do I make friends? How much does this really cost? How do I explain this to my manager? How do I stay productive?
It's a free 6-day email course called “Take Your First Work Trip”.
Over six short emails, it takes on the five fears that came up again and again in those responses. Here’s what you get each day:
Why most people don’t use their freedom to work from anywhere?
What keeps you safe in a new environment?
How to tackle loneliness?
Will your productivity drop?
Can I afford this?
What a workday in your life could look like?
These are the things I’ve learnt after five years of working from dozens of places and making plenty of mistakes.
One of the first people to finish the course wrote:
“Hey Kanak,
I completed all 6 days of the work trip! It was such a good kick-start, and I genuinely enjoyed it. Thanks for putting it together. Looking forward to seeing where you take this next!”
My hope with this course is simple. That one day, instead of thinking, “I’d love to do this someday”, you’ll book your first work trip.
I don’t care whether it is three days in the mountains or a month in another country. I care that you stop letting uncertainty make the decision for you.
Somewhere in the next few months, I hope you find yourself opening your laptop in a place that used to exist only on your saved reels on Instagram :)
Love,
Kanak
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