Go Where the Wind Takes You

One of the fun things about planning a trip someplace far or exotic is the anticipation before the actual journey. Maybe you’ve saved up money for years or you’ve finally gotten the courage to purchase that plane ticket, but once that decision is made the curiosity and wonder have a chance to fully take hold.

Will the people be friendly to you? Are your accommodations close enough to the beach? Will you like the food?

Curiosity is one of the most golden attributes in our universe and there is nothing closer to the feeling of Christmas as a child than getting excited for a trip. But I’m actually here to say stop thinking about it. It’s best not anticipating every detail about your approaching travels, and it’s best not thinking about it much either. Trust me, you’re better off not knowing.

This might sound like some backwards advice from what we are all used to hearing. Aren’t we supposed to be prepared? Yes, of course! If it’s your first time in a country or traveling on your own, you most definitely need to do some research. I’m not saying to skip out on planning for the weather, or researching safe areas to venture, or what type of outlets your electronics will use.

I’m talking about the “what ifs” that will pop into your mind once the essential planning is all complete. I’m talking about the expectations that you most definitely have of the place and of your soon to be experiences there. Get rid of them, cast them aside as they come up in your mind and think of something else. Once your trip is booked and the necessities are planned, don’t let those sugar plums dance in your head.

There is a reason why Buddha said expectations are the root of misery. Well, more accurately “craving” is, but craving creates those misery causing expectations. When you build an image in your mind about a place or experience that you haven’t experienced yet that image is, well.. imaginary! It’s a great set up for a let down. When things don’t quite add up to your imaginary notions, it can be upsetting in both big and subtle ways. The unfortunate reality of this is so spot on even Shakespeare said it.

“Oft expectation fails, and most oft there where most it promises.”

Expectations not only fail us, they most often fail us when we have the highest emotional investment. You might recognize this pattern when a movie based on a book comes out. The harshest critics and the most disappointed people are often the biggest fans of the book, the ones with the most expectations. This isn’t to say that your trip wont be fun if you have expectations. After all, you probably wouldn’t have booked the trip in the first place if you expect to have a horrible time. But you will have a richer and more fulfilling trip if you get rid of them.


When you embark to a place without expectations, or without a preconceived story, you are doing more than inviting a good time or avoiding a let down. You become intimate with the experience. Without notions and judgements, you free yourself to be totally and completely surprised. Not just with the place and things around you, but within yourself. If you don’t already claim to know something, you have a chance to be wowed. Perplexity keeps you aware and in the moment.



Most of us have heard the advice to live in the moment and to “be here now” in order to get the most out of life. If you look back at the times where you’ve been wholly present, you’ll find that it’s not done with words. The moment is something felt, it’s a stillness that invokes a deeper realization of yourself. When we live in a moment and trust that stillness, which words can’t reach, we become fully alive in where we are in a way that cannot be done when we stay trapped in our expectations and preconceived stories.

Not knowing and letting yourself not know, makes the words that paint imaginary stories fade away and invite the real and truly wondrous. Many of the best times I’ve had traveling have been when I’ve planned next to nothing, arriving without even knowing where I’d sleep yet. With expectations and over-planning gone, serendipity has a chance to play. With a more keen sense of presence and a more open eye, you’ll be far more likely to approach that local for a drink or explore around that curious looking corner.

When you travel without knowing you rid yourself of expectations that would otherwise blind you of the true place and experience.

When you travel without knowing you open a window into your deeper self. You let an authentic version of yourself shine through when you let the preconceived stories people have of you and you of yourself, fall away.

When you travel without knowing you invite the serendipitous. Which can lead to even greater adventures you couldn’t have even imagined.