Alternate Route to Silicon Valley

A true account of going the distance to go to work.

Here I am in our young century’s center of global capitalism, grown from the orchards, where revenue and influence scale faster than Moore’s Law. If you come to Silicon Valley with pluck, talent, and an idea for an unmet need, you’ll be rewarded with the California Dream at its dreamiest.


Well, it’s true that if you’re a qualified professional in the right line of work, there’s a preponderance of good jobs here. There’s also a dearth of new residential construction, partly because the current inhabitants are happy to fight for their homes’ rising values — and against more density in their communities. The gross imbalance between job creation and housing availability means that even the most basic shelter in the most anodyne neighborhood is beyond the means of almost anyone, no matter how wildly successful you are by the measure of anywhere else. To some extent you expect the cost of real estate in San Francisco to be astronomical, but that’s not the place I’m talking about. The Valley is a blur of somnolent hamlets quite far from the city you see in postcards.

If you have a family, like I do, and this is where you work, you’ve got two choices: try to scrounge $2.5 million from under the cushions to buy a tiny house in, say, Palo Alto, or find a slightly more affordable community about two hours’ drive from the office — each way.

1268 square feet for $2,498,000. I’m not shitting you.

Actually, there’s another option. Live somewhere else entirely.

Commute from another part of the country.

The Silicon Shuffle

I wake up early Monday morning in my suburban Chicago home, kiss my wife and sleeping children goodbye, and head to O’Hare to catch the 7:15 to SFO. Then on Friday, catch an afternoon flight back to Chicago, get home close to midnight, and kiss my wife and sleeping children again. Pack in some solid family time on the weekend, then on Monday it’s back to work 1846 miles away.

No, I don’t enjoy sitting on airplanes or being away from the people I love most, but it gets a little less painful when it starts to feel like a routine. Maybe you’ve seen this montage in Up in the Air, in which George Clooney moves seamlessly through the airport with an economy of movement and purpose; it’s sort of like this for me, except my mood is more one of resignation, and I don’t look as good doing it.

Travel hell isn’t typically this handsome.

Living and working like this is hard to do, but relatively easy for me to say. While my travel stints go on for a while, they’re temporary. I can take as long a break as I want.

I’m an independent practitioner of the marketing arts — i.e., freelance copywriter and creative director — who enjoys some of the kinder aspects of the gig economy. Chicago, my home base, has a pretty large pool of potential clients for me: ad agencies, design firms, start-ups, and brand-forward companies. But to maximize the opportunities, I put myself out there nationally.

My contacts at Apple must appreciate my services, because they’ve regularly invited me to attend to their communication needs. I’ve made a few visits to the fruit stand for at least a quarter at a time, including a seven-month stretch last year — my longest so far, and probably the limit of what I can handle. For most of my other long-distance clients I can work from my kitchen table, but at Apple that won’t cut it. Too many reviews, too many interdependencies, and too many secrets; I must toil for them in one of their locked-down, windowless buildings in Santa Clara County. (Ask me as many questions as you want about my current project. I’ll just keep giving you smartass variations of “I’m not at liberty to discuss.”) This, then, is the main reason I go to the trouble of coming out here as often as I do.

Here’s a little more play-by-play of the rituals and habits I’ve developed over the course of my 49 trips for this purpose — not that anyone’s counting.

On the Chicago side, my Lyft drops me off at Terminal 2, which has the shortest security line, and after a few blips and zips, I walk briskly toward my flight in Terminal 3 — stopping at that one bathroom that always has a stall available. Lighten my load a bit, then more walking and weaving. I reach my gate just as my boarding group is announced, take my seat (exit row aisle), wait for everyone to get settled, then take a 20-minute nap. Wake up when we’re in the air, have a coffee (black) from the drink cart, watch a movie, get up to stretch and to pee when we’re about halfway, watch another movie, have a water (no ice) with my meal bar, and take another 20-minute nap when we’re close to SFO. Wake up, leave the plane, splash water on my face in the airport bathroom, take the AirTrain to the rental car center, go straight to that week’s Altima or Sonata, then spend 45 minutes on the decidedly un-scenic 101, to the Mathilda exit, to a nondescript building in a business park where the Elks Lodge and Kal’s Bar-B-Q rub shoulders with Apple, LinkedIn, and @WalmartLabs. After a strong day’s work, I negotiate the traffic to the Embassy Suites in Milpitas, an Airbnb in Sunnyvale, my friend’s place in Los Gatos, or my brother-in-law’s rental home in the San Jose foothills. This, then, is the pin at the other end of my commute for the next four days — with countless permutations of alternate routes to shave a few minutes of driving time here and there — until Friday afternoon, when I take the 101 back to the airport, with a stop for gas in Millbrae.

That TGIF feeling is especially acute when the weekend is a reunion with my family, not just two days off. On the return flight, I’m drunk on euphoria and tiny bottles of Woodford Reserve.

My motley cast of airport chauffeurs. So that’s what the fronts of their heads look like.

During the week, my evening travels may take me to the Whole Foods on Stevens Creek, the Costco on Automation Parkway, the Target in Main Street Cupertino (don’t see many parades in this mixed-use development), the CVS on Blossom Hill Road, an optometrist in Santa Clara, a massage therapist in Saratoga (to squeeze the airplane out of my body), a ramen shop in Mountain View, a sports bar in Palo Alto, or some other familiar stalwart of the American landscape to get the food, booze, services, or sundries I need to feel settled and sustained. When I feel like living a little more than that, I stroll through the Stanford campus, hike along Los Gatos Creek, shoot hoops or pool with a friend who also freelances in the area, or have dinner with my former next-door neighbors who now live in Los Altos. Some nights I’ll even suffer the long, winding rush-hour drive to San Francisco, the city at the center of all this fuss, or maybe even Marin County, Walnut Creek, or Berkeley, to see friends who live in these far-flung places. But weeknights are all I’ve got for leisure time, and it’s a hell of a haul to go both ways within a few hours of each other; after one particularly frustrating three-hour drive to Berkeley for two hours of conversation, I took a long break from these kinds of trips.

At all times, my Google Maps app is critical to knowing where to go. And to pass the driving time, I listen to my Spotify playlists, or to Michael Krasny talking California politics on KQED.

My routine is particularly strict when it comes to communicating with my wife and sons. (I talk to the dog too, but he only cares about me when I’m corporeal.) When I’m caught up in my work, and especially when I’m in a different time zone, I can easily lose track of my family’s schedule, so I rely heavily on my iPhone alarms to hit our conversation appointments.

For ease of illustration, I left out the alarms pertaining to my juice diet.

I talk to my boys on FaceTime twice a day, at 5:20 a.m. and 5:20 p.m. my time. These are their windows between waking up and going to school, and between dinner and bedtime; the first is a brief “good morning” and the second is a recap of the day’s events. (That, plus a treacly, rhyming bedtime ritual I’ve done since they were infants. If you think sweet nothings from a paler, more deadpan Jeff Goldbum will help you fall asleep, then I’m your Ambien.) And I talk to my wife during my morning and evening drives. We often text and/or chat during the day, too, but these are the times we know we can count on. I also try to keep my body clock on Central time, so our schedules aren’t too misaligned on the weekends.

Those other alarms? Making sure I catch my flights.

Howdy, Stranger

In January, after a nice long gig in the town where I live, I picked up another Apple assignment and started doing this route again. And there they still were: many of the same familiar faces. I was rejoining my longanimous traveling companions, all of us biding our time in business class and the exit rows. I’ve even started to recognize some of them by their initials on the upgrade list. We acknowledge each other sometimes with a simple head nod, or a verbal “hello again” if we’re sharing an arm rest, but typically we leave it at that. I’ve never been one to chat up my fellow passengers anyway, preferring instead to cocoon myself with quieter forms of diversion. That’s apparently the norm with this group; we’re all more comfortable keeping some psychological distance — to avoid the burden of interminable pleasantries, and to maintain control over how we choose to occupy ourselves for the next several hours.

You may have heard the term “nerd bird” to describe weekday flights between San Francisco or San Jose and other cities with large concentrations of tech companies, such as Seattle, Austin, or New York. But while Chicago has been aggressively pursuing tech legitimacy, billing itself as “Silicon Prairie,” it’s not the nerd stereotypes who dominate my route. Rather, I keep seeing a lot of weathered executives in suits, which is conspicuously at odds with the Bay Area’s corporate culture of bike shares and billionaires in T-shirts. I mean, come on, we’re heading to a region whose pioneers and evangelists — from Robert Noyce to Steve Jobs — have emphatically rejected the posture and dress code of the traditional capitals of commerce. So I can’t help but wonder: where do these men who look like their bank accounts think they’re going? To their West Coast counterparts, are they an anachronistic novelty? Or are they reassuring symbols of pecuniary fortitude from the stolid, responsible Heartland? I can only speculate. (Again, we don’t really talk to each other.) After we land, they and their kind disappear from my view until the next flight we share.

My steadfast traveling companions. See you Monday morning, fellas.

TSA agents. American Airlines gate agents. That nice Avis lady who always wants to help me find my car (thanks, I’ve got this), and the even nicer one at the exit booth. The transgender waiter at Cat Cora’s restaurant, and the Vino Volo bartender who looks like a tattooed Melania Trump — both at SFO. So many faces that I see over and over again, so far from home.

Strangely, I don’t see the same flight attendants as often as you’d think. I’m not on a first-name basis with any of them. They only call me “Mr. Carstens” because they have a device that tells them I’ve given the airline enough business to be granted an identity. Several times I’ve seen the woman with the thick Southern accent who scolds us if we don’t listen to her exit-row safety spiel; I like her, but I’m not crazy about the one who screams the credit card offer like a kamikaze pilot.

Much has been written about the role familiar strangers play in making us feel at ease in our environments. I recognize that every time I move away for greener pastures — something I’ve done a lot in my adult life. This unsung social network disappears, and I have to build it back up again through my new daily patterns. That’s what’s happening to some degree with the way I travel now. They’re good to have, these people I keep seeing without knowing.

But knowing is better.

The Lay of the Land

My brother-in-law moved to Silicon Valley from New Mexico last December. Actually, he’s above the Valley, renting an awesomely strange geodesic dome halfway up Mount Hamilton, which rises east of downtown San Jose.

I call it “The Biodome.” Pauly Shore not included.

“Uncle Jimmy,” as my boys call him, is a bachelor who strives for efficiency in everything he does, reducing the variables in his operations job, his vegan diet, and his small set of belongings; he doesn’t require more than two forks, and those camping chairs work just fine in the living room, thank you very much. This house is tremendously out of character for him — not just stylistically, but because it requires a little bit of a commute to his job in Fremont. The man hates the idea of a life lost to traffic, and still, he chose these quirky quarters partly to provide me with a room, a view, and a shorter distance to my temporary employer. So he’s as generous as he is economical. That, and he found an acceptable 22-minute route to work that takes him on some bucolic back roads.

Uncle Jimmy is either too smart or too wimpy to deal with travels like mine. To him I say it’s the former. After all, he’s giving me a free place to stay.

From this perch, I can see almost the entire basin — from the Santa Cruz Mountains to the south and west, to San Francisco Bay to the north, to the slopes I’m sitting on to the east. I spy a NASA research center, a Great America amusement park, a modest San Jose skyline, planes coming in and out of SJC, signs for chain stores and restaurants, and an awful lot of strip malls and parking lots. Over there, that’s where the 49ers lose a bunch of games. Oh, and there’s the landfill that makes Milpitas smell like yesterday’s diaper. See those shacks down there? The ones with the cars on blocks out front? They’re all worth at least $1.3 million.

At night, all those street lights have the same orange cast with the dimmer on low — I’m guessing to mitigate light pollution, but damn, it’s hard to see when you’re driving.

As much as I appreciate the rectilinear modernism of Mies and Corbusier — I’m an enthusiast, in fact — my senses are dulled by all the glass boxes I see for companies whose names contain “Tech,” “Net,” or the one-syllable sound of a Tourette’s outburst. Did they hire an architect, or are they growing so fast they just picked their buildings from a catalog? But wait, there’s a spectacular exception: the new Apple Park — a.k.a., the Spaceship — surrounded by little beige houses. Like its company, that campus represents a higher aesthetic standard than the rest of Valley. (I was once allowed inside this Shangri-La while it was still under construction. All I can say is, of course, “I’m not at liberty to discuss.”) Unfortunately, this apogee of good taste has a moat around it, and the bridge is drawn for employees only. Beyond its magnificent plot, it’s encircled by concentric rings of blah.

So close to liftoff, and not a millenarian in sight.

Maybe I’m spoiled by the architecture in Chicago, from the skyline, to the public works, to the houses down the street; I live in Oak Park, where you can buy a Frank Lloyd Wright house for half the price of a trailer home in Sunnyvale. Here, in the Valley of the Heart’s Delight — its moniker before it grew silicon — I look to the natural landscape to make up for the manmade one. And it does. Almost.

Uncle Jimmy and I will often sit in his camp chairs, shooting the breeze as we stare out his large, hexagonal picture window. He calls the west the “intellectual property side” of the Valley; that’s where all those venture capitalists, incubators, and famous companies reside — you know, the ones whose products consume way too much of your waking life. He works on the eastern “industrial side,” where the scenery is more frequently visited by trucks and trash. Don’t get me wrong: these hills are quite lovely, especially during the brief seasons of bloom and green. But the best stuff, as in most of California, is closer to the coast. From that distant point and moving in our direction, we can see the landscape go from lush to lean, as though a barber shaved a nice, clean taper across the terrain — from those towering redwoods on the horizon to the low, dry grass surrounding this house. Even when I’m parked in traffic on a lowland freeway, I can lift my eyes to the mountains ahead or the rainbows above. That’s the good thing about the scarcity of taller, higher-density buildings: breathtaking views are available at many levels, and from many angles.

Then, every Friday, I see the upper Midwest’s unremarkable topography — the endlessly flat plains — from an airplane window, and I sigh a little bit. The melancholy evaporates the moment I cross the threshold of my home, when the dog jumps up to lick my face. In between, though, from the O’Hare tarmac to the Lyft ride through colorless exurbs, I have these pangs of discontent, feeling like I’m stuck in a purgatory between two flawed metropolises. It’s similar to the despondency I sometimes feel when I’m driving on the 101 on Monday morning — no matter how brightly the sun is shining — only it has less to do with missing my family, and more to do with my visceral comparison of two very different locations. I keep switching the channel from one to the other, and they keep revealing their relative drawbacks as much as their advantages.

Chicago’s biggest advantage is that my family and I can live here comfortably. Mostly.

Almost Comfortable

JoAnne, the better half of the Los Altos couple who once lived next door, says this about Silicon Valley’s temperate climate: “You’re always almost comfortable.” Meaning it’s a little too warm in the sun, and a little too cool in the shade. That’s her refrain whenever someone suggests the weather almost makes up the cost of living. On the rocky coast, you’ll get some incredible shots for Instagram, but the fog blocks the light, lowers the temperatures, and dampens the spirits. And warm summer nights don’t exist in any of these microclimates.

Another thing that manages to disarm me every time I start a new gig out here: it’s really quiet. And slow. Not just the driving, but the walking and biking. Where’s the hustle and bustle? Doesn’t it take more combustible energy than this to launch all these moonshots? I suppose I should be calmed by this vibe, but it’s too confounding for that. Is this real Zen or artificial Zen? It’s incongruous with the blazing advances in technology that happen in these environs. Put some hop in your step, world changers! Hey you, Googlers dallying like Pee-Wee Herman on your candy-colored bicycles: you’re porting all of human consciousness into your Master Control Program, and this is how you get around? It doesn’t compute. Pedal faster!

I’m not keeping a tally, but the Valley appears to have more Targets and Trader Joe’s locations per capita than anywhere else I’ve been. That’s fine if you need to replenish the basics and don’t want to starve to death. Where’s the cool stuff? The hip shit? The avant-garde accoutrements? For all the designing of experiences and shaping of culture that happens inside these companies, why don’t I see more street art, edgy bands, provocative performances, or mind-blowing installations? Yes, I know, there’s San Francisco and the East Bay, but why not right here?

New corporate art at the LinkedIn building. Nope, doesn’t count.

The longer I spend in this part of the country, the more my browsers, apps, news feeds, and other all-seeing eyes assume I live here. The New York Times tells me what’s happening in California, not Illinois. Ticketmaster alerts me to concerts in Oakland. Yelp has “Cupertino” pre-filled in the location field. If I’m not careful, I’ll be more established here than in the market where I live. While I don’t really consider myself the networking type, I’ve discovered that I can schmooze organically, everywhere I go, just by doing a good job and not being a dick. One result is that I’ve been netting a larger catch of professional acquaintances in these parts, and getting more opportunities to stick around.

Yes, I want the opportunities. The “stick around” part, not so much.

The Lengths We Go To

Before I went freelance, I logged more than my share of business travel — to supervise the filming of TV campaigns, or to present to clients, or to embed myself with pitch teams in other cities and countries. But that’s not the same as punching in at the same time for the same route, week after week. The occasions and destinations in my industry tend to be as erratic as the personalities, whereas this regular routine is giving me a feel for the steady, persistent schlep that governs the biorhythms of people in other professions who travel (so to speak) in my circles.

Vik, JoAnne’s husband, is a healthcare CTO. He’d spend the week at his job in Madison, Wisconsin, and drive home for the weekends. Given his profession and ambition, I suppose it was inevitable that he and his family would eventually move to Silicon Valley. When they did, a couple years ago, his new job had him traveling regularly to — you guessed it — Chicago. He would have had more time with his kids had they stayed put.

They’re moving back this summer, by the way.

My son’s best friend’s dad stays during the week in downstate Champaign, where he works at the University of Illinois. That’s nearly three hours away — about the same as Madison, only in the opposite direction. At that distance, surely you have no choice but to put your head down most nights in a spartan apartment near your employer. Then again, I know of plenty of working stiffs in the Bay Area whose jobs are in Palo Alto, Mountain View, or Cupertino, and who make that kind of drive every day, both ways.

Maybe they have more intestinal (and urinary) wherewithal than us Midwestern corn eaters, or maybe their view of reasonable suffering has been obscured by all the pot smoke drifting from the cars around them.

A couple more examples from academia. My brother who lives in the Philadelphia suburbs has a neighbor who’s a professor at the University of Southern Mississippi. (Guess there weren’t any openings in northern Mississippi.) And I have vague childhood memories of my dad traveling regularly from our home in Oshkosh, Wisconsin, to the University of Minnesota, where he was working on his Ph.D. It’s one thing for businesspeople to make trips like this, but if you’re an academic, are you being properly compensated for the misery?

I witnessed another extreme at the last place I worked full-time, now called SapientRazorfish. (A fish can never have too many intimidating qualities.) Large teams of Indian software engineers were removed from their families and their hemisphere — sometimes for a couple years — to some client’s boiler room in a town like Columbus or Moline, where they typed the code for the next big e-commerce register. They had an endurance for separation and malaise that I can only imagine.

About a year ago, while attempting to make the most of my time in California, I drove my rental car to picturesque Half Moon Bay, only to find myself eating dinner alone at the bar of a restaurant — like I’ve done in just about every other town within a 40-mile radius of my Apple foxhole. I struck up a conversation with the guy next to me, who was in the business of agriculture technology. For fifteen years he’d been splitting his time between his giant farmhouse in Manhattan, Kansas, and a hotel room in Foster City, an engineered landfill on the marshes of San Francisco Bay. He had a daughter in high school who was being actively recruited by Stanford, which meant part of his family might soon be joining him in this dimension of his life. He seemed pleased by this prospect, of course, but at the same time he was wistful; it framed up just how much of her childhood he’d missed.

I have friends from college who work as management consultants or in private equity, and they’re no strangers to the long-distance commute. London to Frankfurt. New York to Chicago. LA to San Francisco, and vice versa. For them, as with me, marriage and parenthood were met squarely with increases in work responsibilities and travel obligations. When my rise through the agency ranks resulted in more time on airplanes and fewer nights tucking in my kids, I would share notes with these guys; we were all developing strategies to keep our families close from afar. Their methods didn’t necessarily apply to me, though, because my travel was irregular and my days inconsistent, with early call times (for shoots), late-night rehearsals (for pitches), and various advertising emergencies in between. I never really knew when downtime would materialize. But in my current professional situation, my travel is a steady drumbeat like theirs, so I can revisit those old notes for collapsing the distance. Mainly, it comes down to those appointed conversations, and to blocking off time when I’m physically present to be mentally available as well — rather than working or, worse, being distracted by worries about work.

Ah yes. Being present. Actually listening to the conversation in front of me instead of the one in my inbox. Tasting my food. Sleeping through the night. I’ve been much more successful at these things since I’ve gone freelance, and that’s one of the main reasons I’ve stayed independent as long as I have — going on four years now. (I wrote some of these prescient observations for the marketing site Shocase when I was a mere six months into my freelance journey. Many of them still hold true.) The biz is full of histrionics, but in this capacity I can help with an agency’s or marketer’s emergency du jour in the most objective and effective way, without internalizing the crisis; I can focus because I’m not freaking out. Take that, add a constant variety of challenges, and sprinkle a nice day rate on top, and it’s a recipe for my professional happiness — even if I do have to lug my ass back and forth across the country on occasion.

Judging from the “you do what?” reaction I get from people at both ends of my commute, it seems my situation is still rather unique. There are other freelancers at Apple who fly in from LA, Portland, Minneapolis, or as far as Boston, and even they ask me how I do it; most of them go home only once or twice a month, if that. (One notable exception: a woman who also goes home every weekend — to Miami. That, to me, is impressive.) I’d say a slim majority of the employees in my group, particularly the younger ones, take the long ride on an Apple shuttle bus from a neighborhood up in San Francisco. Some come from as far as Oakland, or Santa Cruz, or even Mill Valley, which is way, way over the river and through the woods. If you’re driving here from Marin County, add up your weekly commuting time; it’s damn near mine, including my airport and flight time. To you I say: “You do what?”

As I see it, all that flying is the easier part. What’s hard is being away from my family and my home — a much nicer home, by the way, than anything I could afford on this edge of the country.

It’s All Here?

Downtown Sunnyvale consists of a curious little street surrounded by box-store parking lots. Banners on the antique-reproduction lampposts read, “It’s all Here!” You can get a pretty good coffee, beer, or pad thai on this street, or walk to Macy’s, Orangetheory, or yet another Target. Go to the acupuncturist or cryotherapist. Look at your phone in an empty plaza. Or hop on the CalTrain for somewhere that’s, um, there. Not here.

“It” doesn’t appear to include sentient beings.

This pretense of a town center is pleasantly benign. If you only want to subsist without getting hurt, then yes, here it is. All of it.

Good weather, good schools, good cost of living, good commuting times, good people, and a good society, with some occasional bad and a burst of the unexpected to interrogate your perception of what good really is. Where’s all that? Nowhere.

Since leaving the nest, I’ve lived in Virginia, Atlanta, Los Angeles (twice), New York, and Chicago (three times). Almost moved to Seattle, Cincinnati, my home state of Wisconsin, and back to New York. Sometimes I’ve chased the dream job, and other times, the dream location. My eminently patient wife has been with me for most of this wild ride, and in 2011, the kids were uprooted by my wanderlust too; in the span of six months, we moved from Chicago to LA and back again in what I called “an expensive working vacation with all our stuff.” We seem to agree that Chicago is the best place for us — for now, for all sorts of pragmatic reasons.

If I’ve come to any sort of conclusion, it’s that there are no utopias. There will always be trade-offs.

Silicon Valley has its charms and benefits, and there are people here who can’t imagine living anywhere else. I can see why they feel that way, just as I can see why people insist on living in Pittsburgh, Santa Fe, Chapel Hill, or Boston, or as far from America as they can get. Question is, will the industry that dominates this particular spot of earth become less centralized and more distributed, like the vapor it creates? Where once it was an unspoken requirement to be in this intellectual hub of the tech universe to attract the best talent and keep pace with the others, do companies now need to establish themselves anywhere but here—and for the same ends? One thing that’s telling: the wait list for outbound U-Hauls keeps getting longer. There’s an exodus brewing. It will be interesting to see if the Valley’s golden era is irreversibly fading, or if the housing and commuting problems can be solved with one of those signature bolts of disruptive thinking — before all the thinkers take flight in my direction.

In the meantime, I’ll try to remain geographically neutral. And to keep the airplane seat warm for you.