The Beginner’s Playlist for Getting Lost

In The Art of Travel, 2. Getting oriented, Sydney by Brennan1 Comment

As I plug in my earphones and head out the door, I quickly delete all navigation apps from my phone. With the reassurance that I can easily re-download them if need be, I commit to the next few hours of complete reliance on my own intuition and sense of direction. The warmth of the sunshine as I stroll down the street feels nurturing, a positive omen for the start of my journey. I cast a bright smile at a stranger passing by…they give me a weird look. Yikes.

I’ve always made it a point to get lost in every city I travel to. This may sound silly (or psychotic) but there is a romanticism that comes from wandering the streets aimless and alone. Defamiliarizing myself with a place inevitably results in some newfound appreciation for the details that I otherwise would overlook. In New York, I spend so much time speed-walking from Point A to Point B that I forget to stop and quite literally smell the flowers. New York City is blessed with a million little parks scattered throughout its hectic streets, but so often I ignore the bursts of orange, pink, and green flowers that brighten up the surrounding, bleak concrete jungle. I am subconsciously swept to my next destination by the anxious need to fit in as much as humanly possible in one day. Gym, internship, class, club meetings, Bobst, dinner to go…by the time I arrive home, there is no desire to venture out and explore all that the city has to offer. Drained of all energy, I simply curl up on my mattress and let my mind drift off, dreaming of distant lands.

Thus, arrival in a new city without the constraints of routine, relationships, or homework usually means a brief chance at freedom. There’s the opportunity to explore a foreign place without expectation or hurry. In these moments, the unique features of each city stand out and elicit awe rather than anxiety––like the disorganized alleyways of Paris, which appear romantic instead of confusing, or the cobblestones in Amsterdam that become a beautiful historical addition rather than simply something easy to trip over.

Here in Sydney, for example, what started out as annoyance at the distance from our residence to seemingly everything fun or interesting in the city, has gradually developed into an appreciation of the chance to explore local niche spots. Wandering the neighborhood of Haymarket––which I guarantee I never would have visited if I lived in a trendier, younger area––has introduced me to the most authentic Thai food I’ve ever had, a plethora of Krispy Kreme bakeries, and an incredible park practically built for Sydney summertime. The streets around Haymarket/Chinatown are not grid-based, which makes it possible to explore a different direction every time I leave the apartment. Google Maps is helpless in situations like this anyways––as advanced as technology is, an app can get just as confused by sudden dead ends, underground tunnels, and unmarked shortcuts.

After a mere two weeks, I still have the majority of Sydney’s 12,368 square kilometers to explore. I’m sure there will be times when not knowing where I am will be a scary, disorienting moment rather than fun and exciting. Having to approach strangers to ask for directions can feel uncomfortable or potentially attract unwanted attention. Honestly, I’m sure there will be one day where I might just give up and Uber home. Despite these potential negative scenarios, I am still determined to continue the act of purposeful drifting. It is not only an important practice in finding gratitude for the beauty in my surroundings, but also a chance to forge my own path.

The Beginner’s Playlist for Getting Lost

“Loving is Easy” by Rex Orange County

“My Sweet Lord” by George Harrison

“Real Love Baby” by Father John Misty

“Pop Song” by STRFKR

“You Make My Dreams Come True” by Hall & Oates

“Animal” by Miike Snow

“Coming Up Roses” by Keira Knightley

“Walking on a Dream” by Empire of the Sun

“Telefono” by Phoenix

“Que’ Onda Guero” by Beck

“Stuck on the Puzzle” by Alex Turner

(Image: Wandering at Sunset; Source: Brennan Hart)


  1. Brennan, I love this! I relate completely to this, because back in New York I was the same way, always going from point A to B without even looking up from my phone since I felt like I was always in a hurry. Living in a new city means you are given the chance to literally just wander and explore and see where the day takes you. I also love the fact that you included a playlist because exploring is never complete without some good music playing 🙂

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