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The Best Trips Happen Outside of Your Comfort Zone

My best friend and I have a tradition of escaping to a new country every year. This year was Nicaragua. But when we came home, we realized that we never truly got “away.”

The Best Trips Happen Outside of Your Comfort Zone

On a recent trip to Central America, I discovered that I traveled thousands of miles to essentially hang out in my own backyard.


We travel to escape, gain perspective, refresh our minds, and experience something new. But because we’re creatures of habit, we often try to build a mini version of home when we’re in a new place.

When we take trips that are so familiar that they’re effectively our home relocated in a new climate, we often find disappointment rather than reward.

My best friend and I have a tradition of escaping to a new country every year. This year was Nicaragua. But when we came home, we realized that we never truly got “away.”

Neither of us had been, but I had several friends who had, so we asked them to tell us where to go and what to do. Although our friends were well-meaning with their recommendations, their insights quickly led us in the wrong direction.

Friends raved about a small town in the south with stunning beaches, beautiful scenery, and a tranquil atmosphere. We were sold. As it turned out, friends of a friend had built some bungalows in the region with rave reviews and high ratings. Our destination and accommodations were set without a second thought.

We landed in Managua, and a driver picked us up from the airport. The car ride down the dirt roads through cow pastures and sugar cane fields had us ecstatic. Our driver Ortega happened to be a passionate politico. He provided us with a firsthand account of the history, politics, and economy of Nicaragua that we’d never find in a book. The two-hour drive felt like 20 minutes by the time we arrived.


As we pulled up to the bungalows our friends had raved about, a rare silence broke out between my friend and me. The band Beach House played one of my favorite songs on an iPod and Bose speakers. A couple of girls a few years younger than us were lounging on a hammock discussing an art gallery their friend had just opened in a loft in Williamsburg. We were greeted by a friendly guy from Chicago, my friend’s hometown, and he encouraged us to do some yoga with him on the roof. Family-style dinner that night was Italian.

We discovered we’d flown 12 hours to end up right back where we came from instead of a new place uncovering new experiences. In my attempt to create the perfect getaway, I had accidentally isolated us from the locals, terrain, and culture we’d come to visit.

Here are five tips to help you avoid the same trap by getting outside of your comfort zone:

  1. Ask your friends for advice and don’t follow it

    This exercise might seem counterintuitive, but once you eliminate the obvious and expected activities that people like you do in your destination, you have the freedom to discover something new and truly escape the familiar. You can start building your own list of experiences that are unique and unexpected.

  2. Create a vacation bucket list

    Think about what you want to experience before you die, and pick which ones you want to achieve while on your trip. Traveling is one of the best opportunities to check things off of your want-to-do list.

  3. Get advice from insiders

    Plan your trip around tips and knowledge from local residents. There are many online forums, communities, and sites that help connect you with folks like this, including my own, Vayable.

  4. Talk to strangers

    When you’re in your destination, talk to people! Talking to locals is the absolute best way to learn something new and discover the best parts of a place. Even if you don’t speak the language, don’t worry: Google Translate, hand gestures, and sketchpads are your friends.

  5. Walk in a local’s shoes

    Traveling gives us the opportunity to be someone new. We’re in a new environment with different rules and customs. When you spend even an hour or an afternoon living like a local, you’ll gain new perspective about yourself and the place you’re in.

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Jamie Wong is the Creative Braintrust Leadership Expert and Co-Founder & CEO of