Lease Renewal

My parents are in town, which means for four days I have been an unpaid PR representative for a city that makes PR difficult.

On our first walk, San Francisco didn't pull any punches. We stepped around a steaming pile of shit on the sidewalk (twice), the sky was an unyielding shade of concrete, and as we crossed through the Tenderloin, a man violently screamed at a parking meter.

I felt a familiar hot prickle of embarrassment. Before my dad could say anything, I was already preparing deflections: "It's a regional housing crisis!" … "The weather is usually better in the Mission!" … "But the restaurants are really amazing!"

Sometimes hosting friends and family in San Francisco feels like defending a client I suspect may be guilty.

Meanwhile, my parents were having a perfectly lovely time.

They photographed Victorian facades I've never looked at twice. They watched fog swallow Sutro Tower and treated it like a magic trick. They found a cheap dumpling restaurant they declared "incredible" while I mentally calculated that I've spent $14,000 on DoorDash here since 2021.

They experienced the city while I was auditing it.

They're tourists. They get to leave. But I've wired $192,000 to landlords over four years. At that price point, admitting the product is flawed feels like admitting I'm a sucker.

When did I last actually choose to be here?

The average American will spend more on housing than on food, transportation, healthcare, and entertainment combined. Over a decade in an expensive metro, a renter wires somewhere between $250,000 and $500,000 to a landlord. It is, for most people, the largest purchase of their lives.

And almost nobody shops for it.

You moved for a job, or you followed someone. Maybe you graduated and stayed because inertia is easier than renting a U-Haul. Then you signed a lease. Then another. A decade later, you've spent a half million dollars on a city you never once evaluated against alternatives.

I will spend twelve hours researching a new TV. I'll read ten reviews before buying a carry-on suitcase. I have opinions about which protein powder has the best macros.

Then I renew a lease on autopilot in a city I've never stress-tested.

I optimize everything except the thing that determines everything else.

Once you own something, you value it at roughly twice what you'd pay to acquire it. The mug you bought for $5, you won't part with it for less than $10 the moment it's yours.

Cities are mugs you can't put back on the shelf.

You can't unwind the career you built around a particular job market. You can't refund the friendships, the familiarity, the knowledge of which bakery does the best scones. The sunk costs pile up until defending your zip code feels like defending yourself.

So we rationalize. We call tent cities "an urban challenge." We call $22 salads "the cost of living somewhere great." We watch the traffic get worse and the streets get dirtier and we adjust our expectations downward because the alternative is admitting we bought wrong.

We stay in relationships with cities we'd have left years ago if they were people.

So this week I ran an audit of comparable metros. Honest cost-of-living numbers with no sentimentality allowed.

The math is pretty indefensible.

My rent would cover a mortgage in Austin. My grocery bill would feed a family of four in Raleigh. The premium I pay to exist in San Francisco, if invested in index funds instead, would compound into $800,000 over twenty years.

The benefits are harder to quantify: 15 minutes to the ocean. Three hours to Tahoe. My girlfriend lives here. Dozens of friends. A mass concentration of founders and risk-takers and the pressure to build something, which I swear I can feel and which disappears the moment I leave.

I stared at this list for a while and tried to assign them dollar values.

Economists have tried pricing the unquantifiable. There's a whole field called "hedonic pricing" that attempts to put dollar values on amenities. A view of the park adds $50,000 to your home value. Proximity to good schools, another $30,000. A walkability score above 80, $20,000.

But nobody has figured out how to price "spontaneous dinner with friends on an idle Tuesday" or "my dog is best friends with the bodega guy who gives him treats."

My spreadsheet keeps telling me I'm losing, but half the numbers are missing.

What would I actually pay to be able to go hiking every weekend? To stay within a 10-minute drive of six people who would help me bury a body? To remain in the orbit of founders whose ambient intensity makes me work harder?

The exercise felt stupid and the numbers are made up. So maybe the honest answer is: I don't know what these things are worth. I just know it's not zero, and any spreadsheet that treats it as zero is lying to me.

I'm renewing my lease this month, despite the brutal numbers. I'm objectively overpaying for a city that can't keep its sidewalks clean.

I’m reframing my exercise from: "Am I getting a good deal?"

To: "What am I actually buying, and do I know the price?"

I'm buying proximity to people I love. I'm buying the ocean and the sunny days and the particular energy of a city that attracts and rewards risk. I'm buying the version of myself that exists here, more ambitious and more energized than the version that appears when I leave.

That annual purchase costs $800,000 over twenty years. Now I know.

It might not be worth it forever. Next year I'll run another audit. Because the only thing dumber than overpaying is overpaying without realizing it.

I'm not telling you to move and I'm not telling you to stay. But I think you should run your own audit.

When did you last calculate your actual all-in cost of living? The expensive salads and parking? The taxes? The commute?

And on the other side: What are you buying that doesn't fit in a spreadsheet? Can you name it? Can you put a rough price on it? Or are you just assuming the sunk costs justify themselves?

Most people never do this. The city they live in sits outside the category of "purchase." It's background noise, a given.

But it's not a given. Every lease renewal is a decision. Every year you stay is a year you choose this over everything else.

My parents flew home this morning.

They left with photos of the Golden Gate, the sea lions, the crooked street that made my mom queasy.

They had a great trip. Tourists usually do. They get the highlight reel without the invoice.

But I’m still here, still paying. Still stepping around shit on the sidewalk and taking afternoon walks at the beach.

Your city might survive the audit too. Or maybe it won't. Just stop renewing on autopilot and start asking what you're actually paying for.

Up and to the right.