San Francisco has always enjoyed the reputation of a highly desirable city. It seems forever that I’ve heard people say they would love to live in San Francisco. If only there were the kinds of job opportunities that could keep them here. Back in the day, San Francisco was the big West Coast commercial city from which trade with Asia and the East Coast of the United States took place. We know that the state of California got it’s start from the gold rush in 1849 and that San Francisco was the city that sprung up from all that excitement. In my early banking career, San Francisco was the financial center of California and where Bank of America and Wells Fargo operated from. That’s all changed now and for the last 50 years, San Francisco has fed off of the growth of technology and Silicon Valley. I’m no historian of the Bay Area but I imagine that was mostly due to its presence wedged between Berkeley and Stanford, two academic powerhouses that have framed the tech innovation era.
In the early part of my career, everyone wished they could be assigned to work in San Francisco. Then, as the tech boom unfolded, it became more and more clear that if you weren’t in tech, you would be a second class citizen in San Francisco. Somewhere along the line, I know that I stopped liking San Francisco so much, not because I dislike tech, but because it just seemed a bad fit for me. I tried living in Los Angeles for six months and that certainly wasn’t to my liking (and an even worse “fit” for me) and for the last 20 years, whenever Kim and I went to San Francisco, it never seemed like things worked out wonderfully well for those visits. I specifically remember one time in the pre-Uber days when we couldn’t get a cab back to our hotel after a dinner out. I remember us thinking that San Francisco was no New York. Then, despite all the action in Silicon Valley, the city of San Francisco seemed to go through a difficult patch with homelessness and crime, making it a city, that while still highly desirable, somehow seemed challenging to live in or even visit.
We’ve had good friends living in San Francisco for 15 years and back when we were deciding to move to California we actually spent some time thinking about whether we would want to live in the Bay Area, looking at homes in Sausalito all the way down to Monterey. Our choice of San Diego as our retirement home wasn’t made with any denigration towards San Francisco (I’m not sure we could say the same for Los Angeles, which we very much chose to avoid), but like I said, it just wasn’t a good fit for us.
Whenever we visited our friends, we tended to visit them at their weekend home in Sonoma rather than stay in the city. For me, the hills of San Francisco were the biggest barrier to my enjoyment of the city because it always seemed to me that walking around the city was just too damn difficult. I’ve now concluded that while San Francisco is certainly a vertically challenging place to live by any standard, (and even visit), wrestling with the hills of the city, if you’re physically fit enough, has more to enjoy than I’ve previously been prepared to acknowledge.
Yesterday I had a morning to myself in San Francisco and after waking up early at the Mark Hopkins Hotel on Nob Hill (the famous movie venue where both Alfred Hitchcock‘s Vertigo and Steve McQueen‘s Bullit were set), I decided it was my day to conquer Frisco. I took a quick look at the city map and what should not have been a surprise to me was that I was at the top of the hill that went in four distinctly different directions towards the edges of the peninsula. Many of the neighborhoods of the city have names that are familiar like Tenderloin, North Beach, Chinatown, etc., but I wasn’t so sure what that would mean for my walking tour. Instead, I chose to look at the Cable Car routes to use them as a guide. Despite my abundance of energy, I figured walking down hills and on flats and leaving the steep uphill to the cable cars was clearly the way to go. I started by heading north towards fisherman‘s wharf down Mason Street, which runs through North Beach. Walking down some of the particularly steep street sections requires an abundance of attention to one’s footing, but I was in no rush.
The whole way down, following the cable car tracks, I only saw one cable car coming uphill, so when I arrived at Fishermans Wharf and I saw a cable car turning around at the end of the Mason/Powell line, I decided I had better get on board. I took a seat on one of the outer benches since the weather was nice and the air was fresh. As tourists arrived and started boarding, the outside seats filled up first until one Australian man came up to me and asked me to please move over. I told him I was as far over as the bench allowed, wereupon he decided he was going to wedge himself in next to me. I decided to give up my seat to him rather than be squeezed in and he declared that I was “man sitting” and that he was justified in pushing me out. So I rode the cable car from an inside seat up and over the hill down past Union Square to Market Street.
I then walked along Market Street to the old ferry terminal where there is a new 40 foot wire frame statue of a naked woman (I’m told it is quite controversial). As I sat on the ledge at the base of the statue, soaking in my surroundings and watching a likely flash mob practicing their dance moves, a man came up and asked me if I would move. It felt like déjà vu from my cable car encounter. I asked why, and he said that he wanted to take a selfie and I was sitting in the best spot to get a picture of himself in the ass crack of the statue. Far be it for me to interfere with a good ass crack shot, so I quietly moved and walked over to the base of the California Street cable car deciding it was time to go back up the hill. I had bought an all day cable car pass so I was determined to get my second ride on a cable car, but as I looked straight up California Street I could see no cable cars going up or down. I checked the SFMTA website and it said the cable car was running, but after a half hour, I decided the SFMTA website was simply wrong. Now that the city had invented Uber, I choose to Uber up the hill to complete my circumnavigation of the San Francisco Peninsula.
Despite my two seating altercations, I thoroughly enjoyed my Frisco walkabout. I put 11,000 steps in my activity bank, saw the best parts of the city, and I feel like I can say that I like this town at long last.


You have inspired me to get a map of SF! I have no sense of direction, so when I travel to SF for work, I don’t have a good sense of where I am in the city.