Resignation: A city dweller looks back on exploring weekends among San Francisco’s gritty downtown

February 22- February 28, March 4 – March 10

I couldn’t think of a better feeling than waking up on a late Saturday morning and realizing you’re living right in the center of a big city. Just about anything is at your feet, like a quiet cappuccino at Jane on Fillmore Street or a bus over to a deep, cold stroll along the Marina and maybe some shopping or dog watching at Patricia’s Green in Hayes Valley. But I wouldn’t be caught dead heading downtown to Union Square.

Urbanites have their quirks for sure– you pick up a variety of oddities subconsciously from countless souls you come across in a melting pot as any landscape as this well as our quirks. For strangers to each other, all we can be sure of is a mass, mutual love for San Francisco/New York/Chicago/Seattle/etc. and that we are gracious to share. Our own little secret. And that’s how any big city’s downtown becomes the least favorite of all of us here.


In all the sprawl of the uncharted concrete jungle, why would you stay downtown? It’s a tourist destination, a generalized spot watered down to prey on any unsuspecting passerby. Downtowns, we forget to remember, are no secret. The flagship stores and family-friendly food franchises that line the Market Streets and Sunset Boulevards and Broadways all over the globe leave nothing to the traveller’s imagination. And isn’t that why we travel, for something completely new and intriguing to all we’ve ever known? Leave it to the locals to show you a good time, not a legion of other lost visitors. They wouldn’t be able to tell you where the closest Philz is.

On that note, I wake up some Saturdays and head straight to the dead zone of urban sprawl. And why would I ever do that to myself? Prior work obligations, that’s why. For three years now I’ve been a local tour editor for Stray Boots— absolutely one of the best ways to get the most out of exploring a new city and on your own terms. Stray Boots is a New York-based app with hundreds of tours ready at your fingertips, most of these actual scavenger hunts that, either alone or with multiple players, you can get really interactive with the destination as the tours take you down alleys and into famous hat shops for the answers and even great photo ops. And here in San Francisco, you would have found me sometimes aimlessly wandering this little town to make sure all the Bay Area tours are up to date. It’s a given that Stray Boots would create tours around the most popular places on the map. And it’s my job– a job most certainly to be proud about. A job I’ll most certainly be sad to leave.

With the incredible progression in my career as a social media marketer for Wish and the little time I do have left to focus on my weekly musings here on AWBTB, I feel that the time for me with Stray Boots has strayed itself. I find myself wandering along a promising new path that will help me reach my destination, uncertain yet more clear than when I first got my hands dirty in downtown treks nearly three years ago. A chance to walk around a city you love and seem to know in and out was the only excitement a post-grad like myself could encounter– but for the places I go now, I wish they could excite me. Albeit some pretty Victorian-preserved storefronts I see nothing but outdoor strip block malls that make me realize how much more there is to explore not just here, but beyond the boundaries of this city.

I find myself talking down San Francisco a lot nowadays, too. I’ve been here for seven years, properly lived within its city limits for two– and for being a native in the greater Bay Area I do feel at times that I’m outgrowing it. In being a part of Stray Boots I was embarking on my own personal journey to see a new side of my home city, but now all has been seen and the wanderlust is only getting out of hand. I’ve worn these stray boots down and now I shall trade them in for something new– shiny new shoes are always hard to turn down.


I came to the decision to part ways with Stray Boots, but not without an everlasting and most welcomed bittersweet taste. I’ll be glad to know what fun facts are to be found scattered across North Beach and Union Square, forever knowing those routes without batting lashes and able to spew out questions to fellow friends like “who is the Nike goddess modeled at on Union Square?” or “what city were the beat poets trying to get away from [Hint: look up to the entrance at their old hangout, Vesuvio].” For mingling among the crowds of tourists out in full force in North Face and scarves they just bought there made the start of the task before me seem like such a nuisance, but at the end of the day, at the end of this road I’ll be glad to carry this seemingly mundane knowledge about this city wherever I’ll go next. And in remembering them, I’ll always have that little bit of San Francisco, no matter how sick of it I may get at times, that will keep me in awe of its uniqueness.

One of of my most beloved quotes about the world comes from appropriately enough my favorite book, A Tree Grows in Brooklyn:

“Look at everything as if you were looking at them for the first time, and the last time.”

The field work completed for this small but ambitious app will wore this city out for me, just as it got to remind me that someone, somewhere, is always new to this place and will be indebted to the wonders I captured for them– even if I’ve forgotten how wonderful they are to myself.



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