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Jason Silva

Jason Silva

Posted: December 20, 2010 10:05 AM

"Romantic poets inaugurated an era of travel because they were the great apostles of open eyes. Buddhist monks are often vagabonds, in part because they believe in wakefulness. And if travel is like love, it is, in the end, mostly because it's a heightened state of awareness, in which we are mindful, receptive, undimmed by familiarity and ready to be transformed. That is why the best trips, like the best love affairs, never really end." -- Pico Iyer

It might seem obvious, but travel elicits aliveness. Travel purges us from our stupor, awakens our curiosity, and reminds us of an existence freed from the shackles of routine.

This follows an idea I came across in the article quoted above: the goal of travel is "disruption, (or emancipation) from circumstance, and all the habits behind which we hide. And that is why many of us travel not in search of answers, but of better questions."

With this in mind, the ultimate trips are those that teach us something about ourselves; we become enlarged by writing a new chapter in our lives, one in which a few weeks of said travel will carry more weight than a few years of stagnant living.

Yet many times the stress of planning can be overwhelming -- too much thinking can rob the trip of its spontaneity and sense of adventure: How can we possibly find serendipity when we've 'rehearsed' the whole trip before hand?

This is why I was so excited to stumble upon Wanderfly.

Wanderfly could be the ultimate solution for the modern-day digital nomad. You might call Wanderfly a full-service digital travel service powered by a 'serendipity engine' -- just put in a region, dates, budget and 'trip style', and the software creates a trip for you. It's that simple.

Wanderfly might be technology's answer to give travel a sense of poetry again:

"For if every true love affair can feel like a journey to a foreign country, where you can't quite speak the language, and you don't know where you're going, and you're pulled ever deeper into the inviting darkness, every trip to a foreign country can be a love affair, where you're left puzzling over who you are and whom you've fallen in love with. All the great travel books are love stories, by some reckoning -- from the Odyssey and the Aeneid to the Divine Comedy -- and all good trips are, like love, about being carried out of yourself and deposited in the midst of terror and wonder." - Pico Iyer

I had a chance to chat with the CEO and Founder of Wanderfly, Evan Schneyer, and here's two of his interesting musings:

(1) What inspired Wanderfly?

Traveling, of course! More specifically, the fact that traveling itself is such a thrill, but the process of figuring out where to go and what to do there -- especially trying to do so online -- sucks. It should be fun and exciting to explore possible destinations and itineraries for your next jaunt, but instead it's a whole lot of work. You're left to do it all manually, sort through massive amounts of information, and answer very specific questions (e.g., exactly where and when are you going?) way before you're ready to. What if you're just starting to think about a vacation somewhere warm with good food and interesting culture sometime next winter? This is where most leisure travel starts -- with a rough idea -- so we wanted to build an online experience that would let people start simply with what they're looking for and how much they can spend, and get going from there.

(2) It has been said that we are an emerging culture of digital nomads, our 'belongings' live on the web, and we are freed of so much clutter, yet this same web offers it's own kind of clutter -- sometimes giving us too much information -- we can almost drown in it when planning a trip... how does this new reality fit-in with the philosophy behind wanderfly?

I've thought about this one a lot. To start, I'd say that this so-called liberation is unfortunately only half the story. It does feel good to have fewer physical belongings as everything goes digital (I just told my parents, who are moving out of the home I grew up in, that they can trash my entire CD collection). But along with media going digital, so is the rest of communication, and the channels for communication are proliferating like crazy. The baggage I'm talking about comes from having too much access to information that is too unorganized, and this problem is especially true in online travel. Anyone who wants to plan a trip today needs to immediately become a statistician, researcher and event planner, all at the same time, and this is because (1) there's limitless travel information now freely available, and (2) it's very poorly organized on the whole. Couple this with a mindset of not knowing exactly what you want in the first place, and it becomes very stressful very fast.

So when we set out to start Wanderfly, we did a lot of research first before doing any building whatsoever. We wanted to really understand the consumer and the market and the problem we were going solve, and this whole information-overload thing just hit us in the face. No wonder it's impossible to find travel inspiration online: using most of the major travel sites out there is like taking a test you didn't know you were supposed to study for! So we realized from the beginning that Wanderfly would need to be an advanced technology almost disguised as a simple game; we'd be solving a "big data" problem, but not burdening users with all the details (like the fact that we're pulling content from over 20 partners to compile these itineraries!) before they're ready for them. And that's exactly what we've created: a travel site that's simple and fun and encourages people to explore rather than overwhelming them with information. Ironically, it's fairly similar to what a good travel agent does!

"Travel, for many of us, is a quest for not just the unknown, but the unknowing; I, at least, travel in search of an innocent eye that can return me to a more innocent self. I tend to believe more abroad than I do at home and I tend to be more easily excited abroad, and even kinder. And since no one I meet can "place" me ---I can remake myself for better. In this way, travel can be a kind of monasticism on the move: On the road, we often live more simply (even when staying in a luxury hotel), with no more possessions than we can carry, and surrendering ourselves to chance." -- Pico Iyer

For more info, hit up http://www.wanderfly.com/

 

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