Updated: 02/02/2019 | February 2nd, 2019

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 is, 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. One time I was in Thailand, and rather than moving on with my itinerary, I just decided to stay on in Ko Lipe for a month.

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 am a workaholic.

I love improving this site.

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 how I expected. Sure, it removed the anxiety of not knowing how I would pay for the next leg of any 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 blogs to write, emails to answer, content to post, and interviews to do. I loved my work and the ability to work anywhere, but it still came with deadlines and responsibilities—especially if I wanted 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 that was supposed to give me freedom and flexibility had somehow managed to chain me to a virtual desk and made me afraid of the uncertainty that might come if I unchained myself from it.

However, one of my New Year’s resolutions was to work less and play more. I want to better organize how I do work, so I can do less work.

While in Panama City, I met 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 in Panama City an extra week and skipped where I was originally going. I traveled last-minute with her to the small town of Portobelo to see her and my friend JD off to Colombia.

She had invited me with her.

Staring into a pair of blue eyes that could read me far better than I could read them, I didn’t even try and instead went with my gut.

“Ok, I’ll do it!”

Waking up and heading to Portobelo last-minute was by far the best thing I’ve done since I arrived in Central America. Portobelo, a 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 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 the technology and the Internet.

My mind raced 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? 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 so I could 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 the Finnish girl on the boat to Colombia. He was going to Costa Rica, but he decided a boat trip sounded better the morning we went to Portobelo, and he changed his plans right then and there. He too embodies a 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 her 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. 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 time living on an island in Thailand anymore.

I think it’s important to never second-guess yourself when traveling. 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 itinerary.

You don’t have to go anywhere you don’t feel like going.

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 here or I have to do that. I’ve forgotten how travel is always at its best when it isn’t planned.

I’d learned long ago to let go and let travel take you where it wants. Now, travel presented me with a choice to do something great with someone great. But I resisted. And travel, once again, taught me a hard lesson.

The lesson is that travel is all about seizing the opportunities in front of you—especially when they’re opportunities to throw away your plans.

As I realized that the Finnish girl wasn’t going to back, 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!

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