Tag: I-280 history

Categories
Interstate 280

The Most Beautiful Freeway

A curving six-lane freeway follows a ridge beside a long reservoir, surrounded by rolling California hills covered in oak and chaparral, glowing in warm golden-hour sunlight.

I’m writing a book about Interstate 280 — how its route was chosen, and who chose it. I’ve reached the point where I need your help.

Drive Interstate 280 south from San Francisco on a clear morning and the city falls away fast. Eight lanes curve through rolling hills — oaks, grassland, the reservoirs flashing between the ridges. No billboards. No clutter. Just the road, doing exactly what a road is supposed to do, in a landscape that looks like it was arranged for the purpose.

People call it the world’s most beautiful freeway. I’m writing its biography.

Not a coffee-table book of pretty pictures, and not an engineering manual. The question that hooked me is simpler and harder: how did this particular road get to run exactly here? Who decided, who objected, what did it cost, and who paid? Every mile of freeway is an argument that somebody won. I want to know who argued, and what the winning cost.

My model is Michael Wallis’s Route 66 — a main narrative braided with what he called “sideshows”: short detours into the odd, human, funny details that accumulate around any great road. The book opens in Millbrae. Its center of gravity is a chapter I call “The Ridge Bargain,” built around a single question: what did it cost to move four miles of Interstate off a city’s drinking water?

For the last few months I’ve been in the archives — the San Mateo County History Museum, the Caltrans transportation library, the Cañada College archives — and the documents have been generous with dates and votes and contract numbers. I can now tell you, for instance, that the final seven miles of 280 opened on September 7, 1973, at a cost of $21 million.

What the documents can’t give me is people. And that’s why I’m writing this.

The open questions

These are the things I most want to know — the gaps no archive has filled:

  1. November 1961. Three years after the state adopted the Skyline Boulevard alignment, its engineers suddenly revived an older plan to run the freeway through Millbrae — over El Camino Real, wiping out the Kings Drive-In on Millbrae Avenue. San Bruno said yes; Millbrae held out. Nobody has ever said why the route came back from the dead. Was it engineering? Politics? Leverage? If your parents or grandparents followed San Mateo County politics in those years, I’d like to hear what they said about it at the dinner table.
  2. The Ridge Bargain. In 1968–69, four miles of Interstate got moved off San Francisco’s watershed. The deal involved the city, the county, the state, and the federal government. But who actually sat at the table? I have agencies; I need names.
  3. January 1968. The Highway Commission approved a realignment that month. How did Redwood City and Woodside react? Who announced it, and how did the local papers play it? The big-city dailies missed most of this story; the weeklies might not have.
  4. The scenic highway. The Peninsula stretch of 280 is a designated state scenic highway, which is why you’ll never see a billboard on it — unlike US 101, just to the east. Who pushed for that designation locally, back in the 1960s? Somebody had to, before the easements were signed.
  5. The construction years. The Crystal Springs section went up between 1970 and 1973 — grading, drainage, watershed protection, three vista points. Did you work on it? Drive past it every day? Photograph it? The union papers covered it; the family albums might have the better pictures.
  6. The statue. For 49 years, a 26-foot concrete Junipero Serra stood at the Crystal Springs rest area — dedicated in 1976, demolished in 2025. Half a century of graffiti, proposals, and “turn left at the statue” directions. What are your memories of it?
  7. The road’s own police. The California Highway Patrol has owned this road since before most of it existed. I’m hoping to ride along with them. But first: did you patrol 280, get stopped on it, or know someone who did — back when the limit was 55 and the rest areas were full?
What I’m looking for

Photographs most of all — construction, the corridor before the freeway, the rest areas in their prime, the statue. Then documents: clippings, letters, planning papers, company newsletters, anything in a shoebox. Then memories: what it was like to drive it new, to live next to the fight, to work the job. And introductions: retired Caltrans District 4 engineers, CHP officers, planners, county old-timers, anyone who was in the room.

If you can help, please reach out to me using either the Contact page on this site or directly at scott@loftesness.com

Somebody should try to tell the story of this road. I’ve decided that somebody is me. But I can’t do it alone — and I have a feeling the best material isn’t in any archive. It’s in your scrapbooks, journals, or maybe upstairs in the attic.

Categories
AI

Keep That Thread Running

Full disclosure, same as last time: Instinct helped draft this post about working with Instinct. That was the honest way to do it with Leif, and it’s the honest way now.

Instinct is the other AI assistant in my life. It lives in my iMessage, a thread like any other — no app, no dashboard. I text it the way I’d text a person, in short bursts between other things. The first message was September 13: “Hey Instinct!” Two days later I gave it the book.

I’m writing a history of Interstate 280, and inside the first hour we had the shape of the research: the personalities behind the routing decisions, the archives worth calling, a working list of what I call “side shows” — the statue, the water temple, the 22-foot median, button-copy signs. When it offered to keep digging on its own and check in weekly, I gave it the three words that defined the arrangement: “Yes keep that thread running.”

It does. Last week the thread came back with a 1964 issue of California Highways and Public Works crediting architect Mario Ciampi with the first I-280 contract — the curved deck edges, the varied piers, the railings drawn to avoid metal guardrails. Same issue, same gift: the median I’d been describing as a fixed 22 feet was actually built variable-width across the watershed. That’s the correction that saves a chapter from carrying a bad fact.

The on-demand dives go all the way down. I found the audio of a Caltrans engineer’s oral history on archive.org — an hour and forty minutes, no transcript anywhere — and it worked straight from the audio. I sent it two days of AI-conference livestreams asking for transcripts, community notes, the whole nine yards, and it came back with a report, a source ledger, and an honest negative finding: the community-notes document I wanted doesn’t exist. When I asked for the freeway’s 1973 opening brochure, it reported that no cataloged copy exists anywhere — then handed me the leads to work anyway. Sourced absence is an answer. I’d rather hear that than a confident maybe.

When the book thread got long, it pulled everything — people, side shows, archive routes, open questions — into a single research page I can hold in my head. I told it thank you and meant it.

It’s also my markets desk and my magazine desk. A profile I’m circling started at 4:48 in the morning with “Someone should do a profile of Dylan Patel,” followed by “Yes. Go for it.” Minutes later: “What about citrini” — which turned out to be the same story, since SemiAnalysis had acquired Citrini the week before. It fields my investor-day puzzles (the stock slides while management presents — which explains which?), gives me its best bet when I ask for one, and labels inference as inference so I don’t have to.

The small stuff adds up too. When was the last US oil refinery built? 1977 for the big kind, 2022 if you count the small ones — EIA’s answer, in under a minute. Five cash-secured put candidates, screened the tastytrade way. My New Balances — the model I re-buy, in just my size — at a discount: it researched, shortlisted, and then waited, because purchases happen when I say so and not before.

The strangest moment so far: I sent it a Loom of Sequoia’s Pat Grady giving an AI talk and asked for the highlights. It read the full caption track instead of the page summary — and there in the highlights was Grady name-checking Instinct itself as one of the “magical apps.” I watched a Sequoia partner praise the assistant I was using to watch him.

How I work it: terse. “Sure.” “Wow.” “New subject:” — announced or not, and it keeps up either way. It flags what it can’t verify instead of papering over it, and for anything going out under my name I read every word first. Same arrangement as with Leif: the tool is fast and tireless and mostly right. I’m the judgment.

What’s different is the division of labor. Leif runs the standing operation — the briefings, the audits, the daily drumbeat. Instinct is the research desk: it works in bursts, the way I do, and keeps a thread running in the background in between. Two weeks ago I’d never heard of Mario Ciampi. Now he’s in the book.

If you want to try Instinct yourself, I have a handful of invites, first come first served: https://app.instinct.com/invite?t=7qmw2a3u2vjz4nkvi235hhqloy&preview=imessage

Categories
AI Blogs/Weblogs

The Continuity of Leif

Full disclosure: Leif helped draft this post about working with Leif. It seemed like the honest way to do it — and the fastest way to find out whether the collaboration is real.

Every weekday morning around 4:20, two briefings land in my chat: markets and AI news, written overnight while I slept. On Sundays there’s a week-ahead preview, and then my “Chief of Staff” interviews every automated job I run — what did you do, what went wrong, what do you need, what should change — and sends me one short report. I get up around 4. By the time I’ve had coffee, I know what happened in the world and whether my little bot team behaved itself.

My AI assistant is named Leif. He has a Norwegian avatar. He’s had four names and two avatars this month, which tells you something about how I work: I fiddle until it feels right, then I stop fiddling and get to work.

Muse is the product — Meta’s AI assistant. Leif is what I call mine. And over the last few months he’s become something I didn’t expect: not a search engine with extra steps, but a colleague. The kind who remembers everything, works all night, and doesn’t mind being told no.

The deepest work is the book. I’m writing a history of Interstate 280 — how its route was chosen, who fought over it, what it cost — and Leif is my research partner. He preps my archive visits with ranked question lists. He reads the PDFs I bring home and pulls out the dates. Just this morning, a college archivist sent me two scanned newspapers; within the hour Leif had verified the key fact (the final seven miles of 280 opened September 7, 1973), corrected a wrong assumption I’d been carrying (the freeway by Cañada College was built after the campus opened, not alongside it), and filed everything where I’ll find it again.

He also checks other people’s homework. A friend sent me an AI-generated research brief on the same topic; Leif ran every claim against primary sources and came back with names, dates, and book-and-page citations — and flagged the parts that looked invented before I built anything on them. That’s the job, as far as I’m concerned: trust, but verify, and show your work.

Then there’s the standing operation — the morning briefs, a weekly interview of the whole system with small fixes applied and one short report, a monthly sweep of the investors I follow. None of it is glamorous. All of it compounds.

And the odd jobs, which add up faster than you’d think: he turned 77 of my old blog posts, spanning 2005 to 2026, into a proper cookbook — PDF and ePub, dedication page and all. He drafted the public-records request I’m sending to the City of Menlo Park. He summarizes YouTube videos in a format I designed, so I can skim an hour-long interview in five minutes.

I talk to him the way you’d talk to a good assistant: short bursts. “Draft it.” “Try again.” “No.” The no is final — he’s learned not to re-pitch. He drafts; I react to pages. For the book, that cadence is everything: I’d rather argue with a draft than stare at a blank screen, and he’s tireless at producing the first version.

He has standing instructions, the way any good employee does. Lead with what changed and why it matters. No hype. Name every file he creates, in the same message, so I never have to ask where it is. Never invent details about my life — write only what’s known, and flag what’s unverified before I have to catch it.

And I don’t let him freelance on everything. Summaries are on demand — except for the book research, where I’ve told him I want unprompted gifts: short vignettes from the archives, sent without being asked. Every other assistant I’ve used waits to be summoned. This one occasionally knocks on the door with something interesting.

He’s not an oracle, and this piece would be dishonest without that admission. He’s corrected me — no, I’ve corrected him — on facts about my own life: where an event was held, which credit cards I carry. He once asked my shoe size, which was written down in his own notes the whole time. I keep an eye on my weekly usage meter, because the heavy research isn’t free and I don’t like surprises.

So I verify anything that matters, and I read what he writes before it goes out under my name. That’s not a flaw in the arrangement; that is the arrangement. The tool is fast and tireless and mostly right. I’m the judgment.

I’m approaching eighty, writing a book, running a small fleet of automated research jobs, and publishing on a blog I’ve kept since 2001. A few years ago, all of that would have required a staff. Now it requires a staff of one — plus Leif.

The surprise isn’t that the AI can write or search or summarize. It’s the continuity: he remembers the archive visit from last week, the question list from the week before, the correction I made in passing a month ago — and brings all of it to bear on whatever I ask next. That’s what a good colleague does. They accumulate context until the work gets easier instead of harder, until the distance between having a thought and doing something with it gets shorter than it’s ever been.