Never Retire: San Francisco Used to Inspire Me. Now It Just Makes Me Sad.

Walking its streets again, I’m struck by what’s missing—and what Spain gives me that The City no longer can.

Underwhelming and expensive.

That’s how it feels to be back in the United States after living in Spain for months amid the knowledge that it's a permanent move.

Valencia didn’t just meet my expectations—it reset them.

So now, walking through San Francisco, a city I’ve loved and that shaped so much of who I am, I can’t help but feel a low-grade shock at the difference in daily life—at what I used to accept as normal.

Just how underwhelming and expensive is it to be back in the U.S. after four-plus months in Spain?

Let's explore this in today's Never Retire newsletter story.

But first, a necessary qualifier.

I do love San Francisco. It's certainly the place that had the biggest impact on my life. To call it pivotal is an understatement.

My daughter was born there. We roamed that city's streets together within a few weeks after she was born. Every single passion I have today—each one reflected almost daily in my writing—was born in San Francisco.

Cities. Public life. Hospitality. Bikes. I got the bug for all of the above and more in San Francisco. Because San Francisco was an inspiring place.

It made you curious. It made you want to try to do cool shit. It made me a curious guy who likes to try to do cool shit.

At (almost) 50, Valencia makes me feel the way San Francisco did at 25.

So when I talk shit about San Francisco…

I love the place but it feels like it's in trouble.

Silicon Valley Killed San Francisco—it’s over.

It's not like we're not having fun here. My wife and I enjoy walking urban environments even if they're uninspiring. For goodness sake, we trekked seven miles on our first full day here.

But the walk was largely uninspiring. The lack of life and vibrancy on the streets is evident in the absence of tourists and the mountains of people who clearly work in tech.

San Francisco has always been populated—if not overrun with tech workers—however it's more noticeable now with so much of the diversity that used to balance things out gone.

Creatives, non-tech freaks and geeks, Latinos—they’re just not here. Or they're hidden among the whites and Asians, who blend into a monoculture that used to be offset by visible expressions of difference.

The wrong nerds won.

This city now not only fully accepts tech; it's culture is pretty much defined by it.

The conversations you hear in passing on the streets (they're all about work!), the North Face jackets seemingly made mandatory during orientation and training, and prices on everything completely out of control reflect a city that slowly but surely has become a lifeless shell of what it once was.

Sometime over the last year—this is my third visit in that span—the slow erasure of San Francisco’s cultural identity feels complete. The cultural wipeout tech quietly carried out over decades looks finished now.

Mike Judge needs to do a reboot.

San Francisco is little more than a startup’s onboarding video—clean, muted, and painfully optimized.

You don’t feel that vibrancy and energy that once came from people experimenting—with oddball ideas, with art, with how they lived.

It's not to say that tech never contributed to this dynamic.

It did.

It's just that it was one thing when tech merely played a role in shaping San Francisco’s diversity. It's entirely another to have witnessed it cleanse San Francisco of anything culturally meaningful or otherwise inspiring in day-to-day life.

Today's cookie cutter tech worker proves true that people like Steve Jobs and Steve Wozniak were the original and true weirdos and renegades. There's nothing revolutionary about what anybody is doing here anymore.

And this is reflected in the dead vibe, If we can even still call what you feel here a vibe.

San Francisco used to feel like a great city—wild and messy and unpredictably chaotic. Now it doesn't even feel like it lives on its romanticized reputation or fading nostalgia. Issues of homelessness and open drug use on the streets—while omnipresent—don’t feel any worse than they always have been.

Maybe a mix of the city's undue rep as dirty and unsafe (we'll get to that in a future Never Retire newsletter story where I make more direct comparisons to Spain) and Trump killing tourism to places like it put what I hope is a temporary nail in San Francisco's coffin.

But these are all relatively recent phenomenon.

Tech has been the persistent driving force in the social and cultural degradation of San Francisco for at least 30 years. The process appears complete.

Tech didn’t just boom here—it consumed everything else. What was once one layer of a rich, layered place is now the dominant culture. And it's a culture of extraction, not creation.

So the question becomes—

Did San Francisco change—so much over decades of my intimate experience with it and so fast over just the last year?

Or did I? Has Spain changed me as much, if not more than San Francisco did—and in a fraction of the time?

I don't think so. Because I'm not that easily malleable. I know a high urban quality of life when I see it. It's objective fact—it no longer exists in San Francisco. If you argue that it does if you have money, you're fooling yourself.

I’ve just been living a different version of city life—one that still feels rich, alive, human-scale. Maybe what I’m noticing is what it feels like to experience real urbanity—public life in Spain that isn’t a product, a buzzword, or a brand. Urbanity that is—absolutely—accessible to a wider range of people.

But it’s not just about my new perspective. The street life in San Francisco is clearly subdued. In the neighborhoods where tourists less frequently roam. And in once-popular attractions such as Chinatown where you once walked elbow to elbow with locals and people who didn't know where they were going. Now you have tons of space in still-expensive real estate.

The prices here are outrageous. The restaurants and bars—often underwhelming—charge like they’re Michelin-starred just for letting you sit down.

A few hours in, the price shock between San Francisco and Spain really sets in—

That’s for a large latte, a cappuccino, a small cup of oatmeal with blueberries, and a plain croissant.

Meanwhile at Oli Bar in Valencia, my wife and I can each have almuerzo consisting of two drinks, two coffees, olives and two large bocadillos with quality ingredients for 13€—

Not gonna lie—this pizza was good. And it’s harder to find NY style like this in Spain.

But was it worth—

—for four slices? That’s a hard no.

Not when you get a cool spin on Neapolitan pizza, a salad and two beers in a place—La Finestra—that exudes atmosphere in Valencia for 21.60€—

I have been thinking—

There’s a relatively expensive restaurant I like in San Francisco—Absinthe. It has been around a while. The menu isn’t cheap, but when you look at it and compare it to the overpriced formulaic joints that litter the landscape here, you’re likely better off.

When these soulless joints charge $15, $20 and higher for salads, sandwiches and—yes—the right to sit down, Absinthe quickly starts to look like the better value and even more reasonable option for a night out where you go in knowing you’re going to be set back.

We moved to Spain knowing it would be objectively better.

We had a clear vision—and a realistic expectation—of how we’d fit and function in Valencia’s urban fabric. And still, it exceeds every anticipation.

Still, Valencia is showing me what happens when public life is prioritized—when cities serve people, not the flow of motorized traffic. I didn’t leave the U.S. bitter. I left because I was done settling. I left in search of something richer. And now that I’ve found it, it’s not easy to go back to what makes so many American cities feel empty, expensive, and just off.

As we walk and reluctantly pay our way through San Francisco, the question isn’t whether I still love this city—it’s whether this city still retains any of what made it great in the first place, other than it’s natural (and man-made!) beauty.