It all came full circle for me that morning, as I stood on the corner of Post & Powell, when the first two guests arrived to my free walking tour of San Francisco. I learned they were traveling from Sevilla, capital city of Andalucia, Spain, and my “second home.” Sevilla was the first city where I traveled abroad as an eager-eyed, college junior and created countless memories that set me on my path to leading a walking tour of my own.
Walking tours are my side hustle in San Francisco. I feel the most alive when I am creating and sharing experiences that bring people together. I’ve never given it that much thought before because I consider it as a very part of who I am as a person. I took my first tour in Sevilla to pass the time and was delightfully surprised by the rich history that dwells between the Moorish-drawn roads, hidden Jewish quarters, and litany of bars that crowd the city streets. It was one of many reasons why I fell in love with the city and call it my “second home.”
A great career opportunity is what initially brought me to San Francisco as a newly minted college graduate. Tech is the gold rush of our generation and has attracted many to Silicon Valley. While working in tech is my “9-5,” giving walking tours is my true passion. I believe side hustles in today’s economy serve as stepping stones to richer opportunities and enable us to be location independent. My side hustle is an avenue to explore my craft, be independent, and be the master of my own destiny.
Gary and his wife Jamie had been making the trip down to Florida for 20 years now. To escape the rough winters, they sought out the warmth in a familiar place close to the beach. Every year, they reunited with friends from across the continent. Kids attend summer camp, retirees winter in Florida.
The tight knit community was organized and word traveled fast. The community upgraded their vigilance to high-alert; they all knew I was coming. By the end of the task, I had met several of the couple’s neighbors and friends.
Gary hired me through the app his granddaughter recommended to him. After a few initial messages, we exchanged numbers; this was all new to him. The couple needed help with moving their bags from the car to the third-floor, elevator-less, apartment. The sedan was packed efficiently. For the 3-month trip, Gary and Jamie had only brought the necessities. I completed the job in under an hour and we both agreed to stay in touch.
As I was leaving, the neighborhood watchdog called out, “Hey kid.” A couple from Tennessee had just arrived and were exhausted. We introduced ourselves and I told them I could help with their luggage. After a gentleman’s agreement, I opened up the trunk and proceeded to move the contents out of the sedan.
“This is a first.” Words I utter to myself quite often working in the gig economy. I received a task to wait on a contractor and furniture delivery guys. The customer would not be home nor would I meet or speak to him.
I turned off the engine and the valet driver approached my vehicle. I had learned to press the latch on the back of my key to separate the vehicle key fob from the rest of my other keys. I handed him the key fob and, in exchange, he gave me my valet ticket. Most of these swanky downtown condos do valet-only and charge a hefty premium to park your car. I headed into the lobby and asked for the keys to apartment 1207.
This felt a lot like a service where you stay in a stranger’s home in exchange for a fee. Inside the apartment, the dirty dishes were piling up and there were papers everywhere. My client had left some money for the valet on the kitchen counter. I pocketed the cash and opened the heavy sliding glass door to the balcony. I sat down in a chair and took in the immaculate view. I wondered how often my client had sat in this very chair. The half-filled ash tray quickly answered my question. I messaged my customer and updated him that I was inside and patiently waiting.
The task went smoothly and I made my way down to the lobby. I signed out of the guest registration and handed back the keys to apartment 1207. I sent the invoice to my client and I was off to my next job.
Haley and her father plopped down on the couch and watched me get to work. Throughout the first hour I got questions about my technique and how much longer it would take. After a tense 60 minutes, I completed the first drawer. I needed to do the same thing 5 more times.
In researching this job, I came across several resources to fix a sagging drawer bottom. The problem lies with placing too much weight in the drawer causing the bottom to get pushed out of the groove. In my furniture assembly experience, I knew I was searching for a how-to guide on building a brace for the bottom of the drawer. With my new knowledge and parts from the hardware store, I set out for the job.
Back at the client’s home, I showed Haley the newly repaired drawer; she was impressed. I explained that handyman work requires tinkering and most of the time the solution isn’t straightforward. I proposed capping my billable time at 4 hours: 1 hour for the first drawer, 30 minutes for each subsequent drawer, and 30 minutes for research. She agreed to my proposal and we shook hands to seal the deal.
Haley relaxed and told me a little bit more about herself. She flew down days earlier as her ailing father had been hospitalized. A couple of months ago, the family moved the father to an assisted living facility. After an emotional couple of weeks, Haley was just glad to have her father’s dresser fixed. Before we knew it, all 6 drawers were repaired. We said our goodbyes and wished each other the best of luck.
I walked into the lobby and tapped on the digital tablet to sign in. The device directed me to the 3rd floor in building 2, apartment 3107. Inside the elevator, the ominous-looking red cord reminded me of the andon cords found in Japanese auto factories. When pulled, the resulting siren alerted others when a problem arose on the assembly line. I swallowed hard, this place gave me goosebumps.
Mable Rogers opened the door with a big smile. She was excited to have her new dresser assembled today. We made some small talk about the weather and I promptly got to it. In the other room, the tv blasted an infomercial about a roadside assistance product. As I hammered in the wooden dowels, I also got first hand testimonials on the features and benefits of signing up for the product. Although captivated, I still needed to complete another 42 steps before these wooden boards resembled a dresser.
At hour 2, Mable came into the bedroom with apple juice and donuts. This brought me back to the days in grade school when I went over to a friend’s house to play. The snacks and drinks were heavily processed and laden with sugar; it was bliss. We chatted a bit and Mable told me about her children and grandchildren. They were very lucky to have this person in their lives.
An hour later, I completed the assembly. We shook hands and I wished Mable Rogers a good day. Still on a sugar high I opted for the stairs on the way out.
Stuart enjoyed collecting. His most recent passion involved the pursuit of craft beer. The secondary market for craft beer followed many previous trends; enthusiasts bought, sold, and traded with each other. Every so often a highly coveted brewery would announce the sale of special, limited release beers. Stuart needed to get his hands on these special releases. While previous pursuits simply required patience and a cold beverage, Stuart couldn’t get himself to undertake the 2,500-mile road trip.
The sale would start at 10am the next morning. Having never had the patience nor the insanity to wait in line for something, I decided that 8am would be a safe time to start queuing. When I arrived, the scene was utter chaos. The line went for blocks past the brewery. The “real” collectors arrived the evening before and camped out; a community sharing some of their favorite beers acquired from past releases. While in line, I met other hustlers that shared tales of camping out for the latest Jordan’s or Yeezy’s. They had sacrificed a night’s sleep to have the opportunity to double or triple their investment. Today’s mission was no different for them.
7 hours later, I carried a heavy, dilapidated box through the sea of people. Hungry, thirsty, and sun burnt, I had completed my task. I promptly shipped the 5 bottles across the country and I was compensated for my time.
John had been planning his proposal to his girlfriend for weeks now. While she knew that the time was ripe for marriage, she did not expect it would happen today, a Tuesday morning. With all coordination in place, John just needed to press play on his plan.
When I arrived at the suburban neighborhood, John seemed a bit flustered. His job description mentioned something about a marriage proposal, but it was quite vague, most of these write-ups are. John walked me through the plan.
The first delivery I made contained a box of chocolates. The delivery would not raise any red flags as John was unavailable to his girlfriend for the past few days. A box of chocolates to his love signified: “I’m sorry, I love you.” A little while later, I feigned forgetfulness and delivered another package to the house. This time, John sent her an album of memories: inside jokes, pictures, and quotes; the last page asking the ultimate question. In tears, shocked, and bewildered, his girlfriend called John.
By this time, I positioned myself strategically across the suburban lake to capture the moment from afar. To meet her prince, his girlfriend needed to walk outside and go behind the house. After, what felt like 30 minutes, she appeared before John. With rose peddles laid out and champagne nearby, John got down on one knee. Across the lake I received the “all clear,” she had said yes. I moved in closer and switched lenses to capture the moment in portrait. We finished taking photos and I hugged the couple wishing them Mazel Tov. My work was done here.