I ran every street in San Francisco

1,058 miles showed me the city’s beauty, but also its social issues

“What the hell are you doing here?” an overweight man in Army fatigues screamed in my direction as he pointed a can of beer at me like a pistol. I was running down a bleak dead-end street near Highway 101 that I didn’t expect to see anyone on.

I was wrong.

The man’s RV was parked in the middle of the block and he confronted me as I ran past. It took him awhile to calm down, but once he did I spoke with him, and he told me his story.

He was an Iraq war veteran, had PTSD, and was trying to get housed. He was on a wait list, but hadn’t heard anything from the city yet. “It’s tough out here, man,” he said, as he sipped on his Colt 45 tall boy. “Sorry to run up on you like that.”

This interaction made one thing vividly clear: San Francisco had a homelessness problem.

This realization may seem obvious to most people who live here, but for the past decade, Daegu, South Korea had been my home.

I’m from San Francisco, but after being laid off from a startup in 2010, I became disenchanted with the city. I wanted to travel and live abroad. Korea seemed as good an option as any.

So I moved to Daegu, a city of over 2 million people, where I taught English to high school kids. In my time off, I ran. Running was a physical manifestation of my curiosity, and a way to explore my new city. I wound up completing some 40 marathons, and 20 ultra-marathons. I trained in the city and on its trails.

Although I really enjoyed running in South Korea, it can be a deeply conservative country. I didn’t really talk to strangers while running. And something as innocuous as wearing shorts during cooler month could get me harangued.

Once while trail running in spring, a group of Korean housewives laughed at me and pointed to my bare legs. “Aren’t you cold?” they asked, even though it was 70 degrees. To them, running in shorts was insanity.

After a decade in Korea, I was finally ready to come home. Upon my return last fall, I saw San Francisco with fresh eyes. But I also felt alienated — a stranger in my own home town. And COVID-19 lockdowns didn’t make adjusting any easier.

So I did what I often do when I feel out of place. On Oct. 17, 2020, I started running. By June 14 of this year, I had run every street in San Francisco. In total I ran 1058 miles, and navigated 1834 streets. The experience was eye opening, inspiring, and at times, heartbreaking.

Spending all that time pounding the pavement (some 211 hours), I discovered San Francisco’s immense beauty, cultural richness and heritage, as well as its startling class divisions and social issues. I tried to focus on the former, but as time went on I couldn’t ignore the latter.

At first the freedom of the city was exhilarating compared to Korea. In San Francisco, I felt like I could run naked, and not have gotten more than a passing glance. And I found it refreshing to strike up conversations with strangers, and see all the diversity, flavor and individualism this city affords.

Two women in Hunters Point inquired about my challenge, after they saw me run down their street and back again. “Are you running the whole city?” they asked. “That’s cool, good luck!” Somehow they knew.

But there were also dark sides that I never had to deal with abroad. I leapt over feces and urine in the Tenderloin, ran past people living in vans and RVs parked under the freeway, and along Bayshore Boulevard, and saw countless bodies passed out on the sidewalk all over the city.

The fact I’d been in Korea for so long, where homelessness practically doesn’t exist, made these sights even more shocking. I began wondering why homelessness and affordable housing were such big problems in the city.

I’d heard my parents complain of zoning laws in my own neighborhood of West Portal. We have no large outlet stores. They wanted some.

I was also aware of NIMBYs (not in my back yard). I’d seen quite a few anti-development signs on my runs through the city.

This attitude admittedly baffled me after years of living in Korea.

Jogging across San Francisco, I noticed as I huffed and puffed up hills, past parked cars, through intersections, up flights of stairs, around parks, and next to the ocean, how much of the city was dedicated to single-family homes. Many were pretty enough, but it seemed a waste of space compared to what I was used to. In Korea, most of the cityscape was comprised of tall apartment blocks. Only the rich had houses and yards.

Would more apartment blocks help solve the affordable housing crisis in San Francisco? It was hard not to guess that it couldn’t hurt.

Another shock was seeing the homeless encampments the city had sanctioned as a COVID-19 emergency measure. I ran past a few times, and there seemed to be a lot of confusion surrounding mask mandates. Some of the homeless with mental issues didn’t even seem to understand there was a pandemic going on.

I witnessed a man, who wasn’t masked, near the Civic Center pouring beer on himself, before smashing the can on his head and running towards the tent encampment like a football player. Security guards tackled him as he screamed about not being able to enter. An outreach worker came over and explained to him that he needed to wear a mask. I felt bad for everyone involved.

Other times, when I was jogging alone, or walking in a beautiful part of the city such as Bernal Heights, with its amazing views, or on the Great Upper Highway with its sea air and sand, I felt like the luckiest runner in the world.

I tried to daydream as I ticked off the miles on my GPS watch. I imagined I was a 19th century star of the forgotten sport of pedestrianism, or extreme distance speed walking, where racers would drink champagne and cover 450 miles or more in a single race. Although instead of walking I was running, and instead of booze, I consumed burritos, electrolyte drinks and nutrition bars.

But then my running would take me away from the coast, or away from nature, and back into a cityscape again. And the social issues would force me to ask tough questions about zoning, housing and the nature of beauty. As ugly as some might say apartment blocks are (and some definitely are), they are effective at housing many people, with a minimal footprint.

It felt wrong to have so many people living in RVs or on the streets while others fought to keep people out of their seaside paradise.

San Francisco’s raging inequality was my constant companion.

But overall, this massive undertaking made me appreciate San Francisco more than I imagined I ever could. I loved running through the Castro and petting a rainbow dyed poodle, hearing young masked-up buskers sing Janis Joplin’s “Me and Bobby McGee” in Haight-Ashbury, and tasting Puerto Rican style burritos in the Mission.

San Francisco truly has it all, and I experienced that on my runs.

By early June, I had covered 84% the city. Yet as I was running in the Mission, I found myself on the verge of calling it quits. My hips were hurting and my lower back was killing me. I had sores on my feet and I was burnt out mentally, physically, and emotionally.

“Was I too old for this?” I asked myself. I ducked into a cafe for a drink, doughnut and rest. As I was sitting there contemplating my next move, and peering out the window, an octogenarian jogged past in a grey sweat suit and old running shoes. I thought to myself, “If he can do it, so can I.”

Despite its problems, this city still finds a way to inspire.

I completed my challenge on June 14, running every street in San Francisco, including the parts of Treasure Island that are only accessible via the Bay Bridge. I’m still not sure how to feel about my venture. I definitely know the city more now than I did before — for good and for bad.

I suppose Henry Miller was right, “One’s destination is never a place, but a new way of seeing things.”

Photos by Adrian Jue