The Dot Com lifestyle is all about doing things most people can only imagine, and doing it on our terms.

So, there’s no right or wrong way for us to travel.

When it comes to visiting a new city, it’s natural to prioritize what we want to do and see. But how we go about doing that can mean the difference between an average trip and a life-changing one.

underwater bell

Try to make trips events we’ll never forget, by doing our forgetting before we go.

The goal is to just get completely lost along the way instead.

After all, we can afford an open-ended travel itinerary. This can expose us to experiences we never even imagined would come our way.

There’s nothing wrong with doing our homework before checking out a new locale, but there’s also a lot we can gain from throwing caution to the wind and diving headfirst into the unknown.

solo gondola cruise

Here are five reasons why we should intentionally get lost in virtually every locale we visit:

1. We get a feel for the different neighborhoods, not just the busiest ones.

It’s easy arrive in a city and never set foot outside of its most popular neighborhoods. But just because something’s crowded doesn’t mean its the best a city has to offer.

Just ask New Yorkers how often they visit Times Square.

But getting lost in a city lets us see firsthand how its different parts form a unique whole. We see how one neighborhood transitions into the next, each with its own tastes, smells and sights. It paints the kind of vivid picture we don’t get by strictly following an itinerary.

food carts

2. We see the people who actually live there.

What makes a city great? The people who live there, of course.

When we get lost in a city, we see how locals go about their daily lives: The stores they own, the places they shop, the ways they talk, and the foods they eat. Its by observing them that we realize how we’re both alike and different.

Wandering around gives us the freedom to see how a city works on the human level.

Because we’re not rushing from one place to the next, we can sit on a park bench and take it all in for a while. We can even strike up a conversation and ask for recommendations from the people who know the city best. We might even be exposed to unfamiliar cultures and new types of people from whom we can learn and grow.

We won’t get that personal touch if we don’t leave some things to chance.

visit with locals

3. We stumble upon unexpected places we’d never see otherwise.

Sure, its great to knock popular tourist attractions off our to-do list. But if we’re following a rigid timeline, we’re closing ourselves off from the possibility of seeing the city’s hidden treasures.

Allowing ourselves to get lost, however, gives us the opportunity to come across places and things that we’d otherwise have missed. We’ll shop at the small mom-&-pop shops that remind us of home; we’ll walk into a bakery with the best pastries we’ve ever tasted; we’ll see the types of landmarks that locals love and frequent.

We’ll get an alternative view of the city, one that we can’t find online or in a guide book.

Post Alley Seattle

4. We create a travel guide that’s uniquely ours.

There’s nothing wrong with checking out guide books other people have written, but there’s something more special about making one ourselves that no one will ever be able to replicate.

Spending the day getting lost in another city let’s us take as many twists and turns as we’d like. We’re calling our own shots, winging it in a way that only we can.

At the end of our trip, the path we took has your unique stamp on it. There’s a good chance we probably won’t even remember how we got from one place to another.

But we’ll remember one thing: that route is 100% ours.

Jim Morrison gravesite

5. Our phone is always there to bail us out if we actually get lost.

The very idea of getting lost is enough to send some people into a spiral of anxiety.

Why? We can always use our phone to get out of a tricky situation.

After all, wandering around a city doesn’t mean we’re trying to create some sort of puzzle that needs to be solved. There’s nothing that says we can’t be lost in a new place if we’re still occasionally checking whether we’re headed toward a new part of town or a neighborhood we’ve already trekked through.

We don’t have to go completely off the grid just to go off the grid.

And if we seem to be on a one-way route to oblivion?

One acronym: GPS. Two other options: Über or Lyft. How tough can it be?


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