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Letting go and letting loose in the hills of San Francisco

by | Apr 4, 2024 | Culture, In The Mag! | 0 comments

Stories from a solo traveler about trying something new

The acme of 2024 occurred early, just how I wanted it to. It was a snowy January week when I impulsively booked a solo trip to San Francisco. I’m still not exactly sure why I did it. Maybe it was because I wanted a change of pace from Edmonton’s icy streets and frigid weather. Maybe I knew that graduation was around the corner and wanted to do one last reckless thing — one last hurrah before life as I knew it shifted into a 9 to 5 schedule in an air-tight cubicle with no windows or fresh air, let alone a view of pacific-ocean waves and cars racing over the Golden Gate Bridge. 

Up until February’s reading week, I had never been on a trip by myself. I had travelled before, with friends and family, but never on my own. And it wasn’t even the travelling part that I struggled with, it was the vacation part once I got there that gave me a disquieted feeling.

As someone who lives meticulously by relying on organization and schedules, I wanted to take a step out of my comfort zone and go with the flow. (This meant not making a travel itinerary.) And, it was all going smoothly, until I arrived at my residence in Bernal Heights with nothing to do and nowhere to start.

It took me the first day to acclimate to the busy city and new ways of getting around. San Francisco isn’t the most walkable place, unless you’re calf-dominant and aren’t afraid of a few steep hikes just to get to the nearest coffee shop. But, allowing myself to explore opened my eyes to a whole new world of travel. I took bumpy cable cars, busy buses, and even busier trains. I visited eclectic restaurants and studious cafés. I stopped by used bookstores and vintage shops. I even popped into an art gallery that I passed on the street, merely because I thought it looked cool. 

On the last evening before heading home, I had a strange sensation. It wasn’t from the sunburn I got in 25 degree weather, taking the wrong bus down to Daly City, or the sharp aches of shin splints from the 500-metre incline walk up to where I was staying. It was the sense of discovery. The discovery of things I was proud of over the past few days, and a few things I wish I did differently. 

These are the three things I learned from my short journey. 

Get out of your comfort zone.

Facing my travel anxiety stemmed from something a lot deeper than just getting on a plane and showing up in a new city. It stemmed from doing the things alone that most people do with others. The thought of sitting alone in a restaurant or walking through a museum by myself haunted me. All I could imagine was someone approaching me to ask if anyone else would be joining. And then the worst part — having to reply, “just me.” 

As the trip went on, I started to feel peace and find fulfillment in doing what I wanted to do. When you travel with others, you’re at the liberty of what “the group” wants to do, like getting forced into hitting up shitty dive bars or being dragged along on your friend’s boyfriend’s ATV trip. It was nice to make my own decisions for once. It was nice to not feel like I always had to make my trip “worth it.” 

On the first day, I took myself to brunch. The idea of sitting alone in a restaurant was not one that I was fond of, but I needed to eat and wasn’t about to stop by the Chick-Fil-A for a quick bite when I knew there were so many better spots to try. I kept thinking about that episode from Sex and the City where Carrie Bradshaw takes herself on a lunch date with no shame. So, what was stopping me from doing the same thing? I found a quaint little restaurant called Plow and requested a table for one. 

As I waited for my almond flour pancakes with a side of fresh citrus fruits while sipping on strong, hot coffee from an outdated pot with a wooden handle, I had an instinctual need to go on my phone. But, this restaurant was lacking the one thing I was hoping for: Wi-Fi. I didn’t have anything with me other than my wallet, a pair of sunglasses, and an old receipt in my pocket from the airport Grab-n-Go. So, I just enjoyed — the view, the food, the people around me, and the sunshine poking through the big windows and hitting my face in a perfect golden glow. I’d like to think that Carrie would have been proud of me. After all, it was her that said the line which gave me the courage in the first place: “So, I sat there and had a glass of wine. Alone. No books, no man, no friends, no armor, no faking.”

Get lost — literally and figuratively.

On the third day, I got distracted on the cable car and missed my stop… by 24 stops. I ended up down by a small area called Tenderloin, which I would like to refer to as the armpit of San Francisco. Thank God for Google, because it was my only option to see which bus I needed to take to get back. Then, my phone died. Typically, my first instinct would be to panic, which I did. But, then I realized that not having my phone wasn’t going to stop me from getting around. Sure, I couldn’t order an Uber or call my cousin and beg them to make the drive over from Oakland to come and rescue me. What I could do was keep walking.

So I walked up the hill. Up, up, up. Until finally I came across a bus stop with an image of the routes on it. I figured out I needed to take the number 30, which ironically only came every 30 minutes, and I waited another 20 for it to pull up. When I finally got onto the bus, it was an hour-long ride back to where I was staying. By the time I was dropped off, I had a disheveled appearance, sore quads, a dead phone, and a crabby attitude. I also had 25,000 steps under my belt. Some you win, and some you just barely come out the other side. This one was the latter. 

Don’t be embarrassed to be a tourist. 

During my visit, I had four packed-full days — full of taking cable cars around and trekking up the city’s steep hills. Everyone was really friendly, but, even being the outgoing person that I am, I found it difficult to talk to people. Other than my dad’s cousins who lived on the other side of the bridge, I didn’t know anyone in San Francisco. At home, I’d have no problem talking to new people. But here, the idea that played out in my head was just… embarrassing. I was worried that the exchange between a stranger and myself would go something like this: 

“Are you from around here?” They’d ask.

“No, I’m visiting from Canada,” I’d say.

“Oh wow, Toronto?” 



“No, Edmonton.”

Only for them to reply, “What’s that?”

So, I had to make a decision to keep to myself and make this the most solo solo-trip to ever exist, or step outside of my comfort zone and make the effort to talk to strangers. There’s a part of me that regrets not having the confidence to be myself to the fullest, but even though it didn’t go the way I had hoped, I can look back and laugh at it. 

On the second day, I visited a coffee truck called Philz near the Marina District to go for a walk down by the water. The lineup was down the block and I could barely hear anything with mariachi music blaring through the outdoor speakers and the workers yelling out orders. When I glanced up to the middle-aged bald man in the window who was at least five feet higher than me, I yelled my order, “ICED DANCING WATER WITH OAT MILK PLEASE.” Each blend of coffee had a distinct, cutesy name: “Dancing Water”, “Philtered Soul”, “New Manhattan”, things like that.

The man, who I suspected was Phil himself, replied, “Six fifty.” Rip off. When I handed him a wad of cash, mostly one-dollar bills, he looked surprised. “Wow! I barely ever see cash anymore. Are you a tourist?” he asked. I froze. I just didn’t want to admit I was visiting so I made something up on the spot. “No. But, I get tips from work in cash, so I always have some on me.” Whew. Good cover. Now he’ll think I’m a cool, young San Fran local, give me my coffee, and I’ll be on my way. “Where do you work?” he replied. That’s when I realized my little white lie had quickly become a big fat fib. Trying to save face, I said with a laugh, “Can’t tell you.” Then I grabbed my overpriced coffee from the elevated concession shelf, and quickly slipped away into the crowd to avoid any more unwarranted conversation. Looking back now, between the one-dollar bills and my vague answers, there’s a good chance he thought I was a stripper. 

On the last day in the city, I bonded with a girl around my age beside me on the bus. It was over the simplest thing — the fact that we were both wearing Hoka running shoes. She introduced herself as Emily and we chatted for the 30-minute ride up to the Golden Gate Bridge lookout. I didn’t think it was worth getting her contact information, knowing that I would be returning home the next day. But, before getting off at my stop, she invited me to meet up with her running group to train for the San Francisco summer marathon. The conversation about shoes must have given her the impression that I was actually a runner, and not just someone who enjoyed daily walks with a coffee in hand or the occasional 5 kilometre jog. Unwittingly, I was once again embarrassed to admit I was a tourist. I couldn’t just say, “Thank you, but I’m not from here.” It seemed awkward for me to admit; I didn’t want to backtrack. I mumbled, “I’m not quite ready to run a full marathon yet, but thanks for the invite.” She smiled. The bus stopped abruptly, the doors opened, and I hopped off, leaving both Emily and my imaginary running career behind me in a back-row seat. I’ll probably never see her again. 

I spent the rest of the day regretting not giving her my number and admitting that I was a visitor. Who cares if we don’t live in the same city? Good friends are hard to come by, and I wondered if I had missed out on an opportunity to have made one.

Learn from it. 

Being embarrassed can make you miss out on great things. Whether it’s a conversation with your quirky bald barista working the coffee truck or a nice girl on the bus beside you. I think I cared more about what people thought of me than how to make the most out of my experience. And that’s the one thing I wished I did differently. 
Stepping out of my comfort zone wasn’t actually as always as scary as I thought it would be. Sometimes, it may even be for the best. One day, I hope I can look back to that five-day solo trip over reading week. The one when I did try something new. The one when I spent my days improvising plans, talking to strangers, and soaking up the sun. The one when I took myself to nice restaurants and trendy cafés. The one when I didn’t worry about getting lost or walking 15 kilometres in flip flops. The one when it was just me, myself and I, letting go and letting loose in the hills of San Francisco.

Payton Phillips

The Griff


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