I didn’t go out much as a teenager. My whole world started with the first period bell and ended with quiz bowl and math team practice. My friends kept similar routines, and our parents drove us everywhere. For me, independence was a Metro ticket for the occasional afternoon at a Smithsonian museum. I had little interest in learning to drive, and in my indifference, missed out on a supposed classic American rite of passage.

After I graduated from college and moved to San Francisco, I met my cousin for dinner. She told me about her early days in town, when she shared a one-bedroom apartment with two other young women. I was enthralled by her maturity and her sense of adventure.

In her lifestyle, a car would have been an indulgence, and anyway, she had grown up in Pittsburgh, where she never needed one. Only now, after moving to the East Bay and having a child, did she resolve to finally get her license. She sounded stressed out from the urgency of learning by necessity. She told me not to be like her and suggested that I learn to drive before I turned 30.

I didn’t take immediate action. The idea rattled around in the back of my mind for nearly a year. When I finally looked up some driving schools one April evening, I was more concerned with the trouble of booking a two-hour appointment than I was with the whole project of acquiring a major life skill.


During my first lesson, my instructor, Jay, asked me why I wanted my license. I admitted that I didn’t actually want it very much. My favorite pastimes kept me in the city and I didn’t associate any excitement with the open road. It was a badge to earn, just so that people would stop asking me why I had never gotten around to it.

As I explained this to him, I realized how defensive I had become. Much more than just wanting the freedom to go shopping and haul a bunch of heavy things home, I wanted to stop feeling judged. He seemed to take me at my word, but assured me that under his tutelage, I would not only become a good driver, but an enthusiastic one.

I had never thought of myself as someone afraid to drive. I figured that I just didn’t like cars very much. Looking back on my chronically sleep-deprived high school career, I think I wouldn’t have been the safest person behind the wheel. Graduated licensing was also a major deterrent. Logging Maryland’s required number of practice hours seemed like the least appealing way to spend any given weekend.

Despite my misgivings about the whole endeavor, my conversations with Jay were friendly and easy. Having something fun to anticipate made me eager for each lesson. But most of all, Jay’s quiet confidence in me eased the pressure I had placed on myself. What if I’ve waited all this time only to find out that I’m a terrible driver and can’t do it at all?

At the end of June, after nearly ten lessons, Jay picked me up at my office. We had an appointment at the DMV, so I didn’t have to wait long. My examiner didn’t seem to pay much attention to me as he casually suggested left and right turns that brought us up and down Divisadero and the Panhandle. I passed my test, drove back to my office, and thanked Jay for his many hours of calm guidance.


When you live in a transit-rich city and don’t own a car, the road test is far from the end of the story.

During our lessons, Jay had told me exactly what to expect from the San Francisco DMV. Road tests are bound by their surrounding area, and thanks to the geography of the Haight, San Francisco doesn’t test highway driving or parallel parking. Jay also reminded me that driving in the real world would require a host of other skills.

Without my own car, I would never get much incidental experience, so I scheduled myself a lot of deliberate practice. I made a reservation at my local Enterprise, signed my name, and received the keys. On that first day, I couldn’t get this disbelieving refrain out of my head. You’re trusting me with this. You think I’m responsible. Don’t you know that I just turned 23 and have never even driven across a parking lot unattended?

Enterprise had plenty of sedans, but never guaranteed a specific model. As a result, I got the opportunity to sample a lot of different cars. I started out with a reassuringly basic Honda Civic, but my favorite rental car was the blue Jetta that I took on my first drive to Santa Cruz, down along Highway 1 via Devil’s Slide, then back on Skyline Drive.

On an idle afternoon during Memorial Day weekend, I took two of my city friends down to the Santa Cruz boardwalk. As an insufferable east coast transplant, I whined about the wind and the cold water. Jeremy quipped that he had never before seen so many people wearing so much clothing at a beach. We strolled past touristy food and did a double-take at the “Warning: water is unsafe” sign in front of a little river full of people.

Heading home, we stopped by the side of the road to peek at a quieter beach and gaze out from the seaside cliff. On our way back to the car, we took a short detour on what looked like a trail, then noticed some tracks embedded in the path. Shawn and Jeremy wanted to investigate further, so we followed the tracks north until we found a lonely old train.

The train’s rounded top gave me pause, as well as the fact that it had been sitting here long enough to accumulate some graffiti. I stayed behind on the ground while my friends quickly scaled the ladders and posed for photos of themselves strutting around on top of an oil tank.

Photo by Shawn Wilsher from the top of a 7-car British Petroleum train, formerly parked just north of Santa Cruz along Highway 1

Part of me wanted to tell everybody about this found playground, but another part wanted it to be our little secret. In fact, thanks to the weak cell signal along Highway 1, it proved fairly difficult to describe the exact spot. During another trip, on his way to Monterey, Shawn checked for the train and found that it was gone. Realizing that the train wasn’t so permanent made me glad that we had gone exploring and found it together.


By the time I was finally eligible to join Zipcar, one year after getting my license, I had become the primary driver in my household. This was no small feat, since both of my roommates had been driving since they were sixteen years old. I’m still proud of this accomplishment. I was also relieved to find that I didn’t feel defensive anymore. Conquering that was one of the most valuable gifts I’ve ever given myself.