Last Updated: 2/9/22 | February 9th, 2022
Sometimes it’s good to travel with absolutely no plans, and sometimes it’s good to have a rough itinerary.
No matter what your choice, it’s important that you remain flexible.
When I first started backpacking in 2006, I remember jumping on a train to Amsterdam on a whim. After I left there for Spain, I missed the city so much, I spontaneously flew back to Amsterdam and lived there for two months.
However, recently I’ve become more rigid in how I travel. I like to work, and though I might (sometimes) complain that having a website means I can’t go off the grid, the truth of the matter is that I love improving it. I am a workaholic.
I got this work ethic from my parents, and I’ve never gotten rid of it.
But having a job quickly changed how I traveled, and not in ways I expected. Sure, it removed the anxiety of not knowing how I would pay for the next leg of a given trip, but it replaced that uncertainty with a different kind of anxiety: the kind that comes from responsibility.
Before, I was a carefree traveler with no obligations and complete freedom. I could do what I wanted. Now, I have blog posts to write, emails to answer, content to post, and interviews to conduct. I love my work and the ability to do it anywhere, but it still comes with deadlines and responsibilities — especially if I want it to keep paying my bills.
This website often doesn’t give me the flexibility to make crazy changes in my plans like I used to be able to do. This job, which was supposed to give me freedom and flexibility, has somehow managed to chain me to a virtual desk and made me afraid of the uncertainty that might come if I unchain myself from it.
However, one of my New Year’s resolutions is to work less and play more. I want to better organize how I do work, so I can do less work and enjoy more travel.
While in Panama City, I met Heidi, a Finnish girl who only “goes with the flow.” She makes no plans and doesn’t carry a guidebook, computer, camera, or phone. They are all things that weigh her down, she said. She was my opposite.
But I immediately liked her.
Because of her, I stayed there an extra week and skipped where I was originally going. Then she invited me to the small town of Portobelo to join her on a slow boat to Colombia.
Staring into a pair of blue eyes that could read me far better than I could read them, I went with my gut.
“OK, I’ll do it!”
Waking up and heading to Portobelo at the last minute was by far the best thing I’ve done since I arrived in Central America. This town with no Internet, no good beach, and no fun activities to speak of ended up being my favorite spot in Panama. The locals were friendly and talkative, spending their nights hanging out in the town square. This was the only place in Panama where I really enjoyed the local food (it had spices and flavor!).
But then, the day before we were set to sail, I got cold feet. It wasn’t the sailing, it wasn’t Heidi, it wasn’t Colombia. I was afraid of being offline.
Because, unlike Heidi, I couldn’t just walk away from technology and the internet.
My mind was racing through worst-case scenarios. What if something happened? We’d be out on the ocean and I wouldn’t be able to fix anything. What if I missed an interview? An ad deal? What if a reader had a problem reaching out to me? What if, what if, what if!
I didn’t go. I told her I would take the week to work then join her in Colombia.
“You get there in seven days, right? Email me when you arrive, and I’ll hop on the next flight and meet you. This way,” I continued, “when I see you again, I’ll be disconnected from the web and we can enjoy Colombia.”
“OK,” she said. I could sense the doubt in her voice.
“I’ll see you in a week,” I said, kissing her goodbye.
As travelers, it’s important that we are willing to change our plans at a moment’s notice. My friend JD joined that Finnish girl on the boat to Colombia instead. He had been planning to go to Costa Rica, but he decided a boat trip sounded better the morning we went to Portobelo, and so he changed his plans right then and there. He too embodied her go-with-the-flow attitude.
I recently read the book Blink by Malcolm Gladwell. In it, he says that while we can overanalyze things, it’s the split-second gut decisions that yield the best results. Sometimes we just know what feels right.
I never heard from Heidi again. As I continued around Panama, I checked my email each day in hopes that eventually, one day, I would hear from her, but I never did.
I understand why she ghosted me. Here I was, a guy who chose work and technology over sailing to Colombia with a beautiful woman who liked him. We were fundamentally different people, I guess, and she probably just wanted someone who was more carefree.
This was a wake-up call.
I had set out on my travels because I wanted to live instead of work. But as my blog took off, I found that the same old work/life problems were rearing their head again. If I wasn’t sightseeing, I was working. Though it didn’t make my trips less fun, it did make them less carefree. There’d be no sudden sailing trips to Colombia or living on an island in Thailand anymore.
I think it’s important to never second-guess fortuitous opportunities. That place you were going to go will still be there in the future, but the people you go with and the experiences you are about to have won’t be.
My Finnish friend was right.
Just go with the flow.
If you want to spend more time with people, go with them.
Don’t get caught up in your preplanned itinerary.
You don’t have to go anywhere you don’t feel like going if something better comes along.
As a digital nomad, I think it’s easy for me to get trapped in the job. The internet will always take as much time as you give it. I get stuck behind my computer and stuck in my itinerary, and I feel that I have to go to X or do Y. I’ve forgotten how travel is always best when it isn’t planned.
I’d learned long ago to let go and let travel take you where it wants. Now, it had presented me with a choice to do something fun with someone great. But I resisted. And once again, I learned a hard lesson: that it is all about seizing the opportunities in front of you — especially when they’re chances to throw away your plans.
As I realized that the Finnish girl wasn’t going to reappear, I resolved to never forget why I began traveling in the first place.
I’m grateful for this experience in Portobelo, because it made me realize that I do need to go with the flow more. I need to forget about the computer and open myself up to change and spontaneity.
Because, after all, those were the reasons I left the cubicle in the first place.
Somewhere, that girl agrees.
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
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Need Help Finding Activities for Your Trip?
Get Your Guide is a huge online marketplace where you can find cool walking tours, fun excursions, skip-the-line tickets, private guides, and more.
Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.