Working From A Second Home In The Winter
Leaving Chicago For Los Angeles
Every year, by late October or early November, we revive our hopes and fears about the upcoming winter in Chicago. With childlike naïveté, we mistake a sunny day in mid-November for a sign of a mild winter to come. Then we read the predictions of the cruelest winter ever to arrive, based on some arcane constellation in the Pacific Ocean, and so we make plans to escape the city. Life is too short to spend 6 months in agony, yearning for the summer to return and counting the remaining days of winter.
Some people enjoy the privilege of a second home in warmer climates, which often means Florida — either by family inheritance or as a fruit of hard work. Florida is not for me, although I tried. The trouble with Florida is that it only has two cities with any culture to speak of, Miami and Palm Beach (sorry Naples). They used to have some old tropical charm, but now they have been taken over by fast and new money which tends to annihilate any kind of charm and culture. Unless you are in residential real estate or financial asset management — which includes crypto in the case of Miami — both places are not conducive to work. Above 80 degrees I get an affliction of holiday brain, and the inescapable drink at noon destroys any half-hearted attempt at getting work done.
Post Covid, many of us are still redefining our lifestyles. Where do we want to live? How do we want to work? I have a friend who packed up during Covid, with a firm plan to drive from Chicago to San Diego, where he never arrived. Instead, he spent weeks skiing in places like Whistler, Canada, or paragliding in Santa Barbara. All the time, he kept working from temporary homes (WFTH), which could have been a friend’s couch, a bus or a tent in the wilderness. Last I heard, he was snowboarding in Kyrgyzstan.
Unlike any other country that I know, everyone in the US is constantly thinking about a better place to live, at least for a few months of the year. For some it’s about taxes — Illinois has some middle of the range state income taxes and prohibitive estate taxes, while Florida and Texas have none. For others it’s about crime — an area where Chicago leads in less admirable ways. Cost of living is important too, and it’s a reason why people leave the big cities and move to the countryside or the rural South. And warm weather is an irresistible attraction to everyone who lives north of the Mason-Dixon line.
My wife Molly and I need and want to work, so we decided to rent a place in Los Angeles this year. L.A. triggers an astonishing amount of ambivalence or outright animosity in Americans, similar to New York City. There are people who would never set a foot in this town, for political, cultural or safety reasons. Very timely for our visit, a local bishop was murdered, presumably by his housekeeper’s husband. In many people’s imagination it’s an expensive version of Sodom and Gomorrha, where dangerous homeless people roam the streets in search of drugs (Skid Row truly looks like a modern-day version of Brueghel’s painting of hell), MS13 gang members with face tattoos kill people randomly, and the whole state is governed by a lunatic fringe of liberal spendthrifts. There is a small grain of truth in this, but similar things can be said about other big cities in the US, and we like to criticize with fervor. L.A. is a picture book of extreme differences, as is the whole country, and there are large islands of serenity between scattered craziness.
We leave Chicago on a cold and snowy day in the middle of February, which makes our departure easy, but the drive slightly more difficult. Since our dog has grown from a 12-pound puppy to a 77-pound 5-year old, airlines would have turned us away at boarding, despite an easily obtainable service dog pass. We embark on a 6-day trip — Molly, Ben and I — an average of 8 hours of daily driving through the Midwest and the Southwest. We will pass through Missouri, Oklahoma, Northern Texas, New Mexico, Arizona and finally get to California.
My visions of Missouri and Oklahoma are naturally filled with prejudice, as it is normal for an arrogant city dweller like me. I find my preconceptions fulfilled every time we refuel the car off the highway. Dilapidated houses with no-trespassing signs and rusty trucks outside. These are the kind of neighborhoods where you don’t want to ignore the warnings, because people may shoot you through their door. Oklahoma evokes memories of historical events of oppression and massacres of black people and Native Americans, but then — to my surprise — Oklahoma City turns out to be a friendly, modern town.
A random guy stops his car in the middle of the street to yell how much he loves our dog. In Chicago, we pride ourselves on our diversity and our multicultural traditions, but we live strangely segregated lives, and the relationship between the white and the black community can be tense at times. Here, we receive warm welcomes from everyone in the street, black or white.
There is a thin stretch of rectangular land that divides Oklahoma from New Mexico. It’s Northern Texas and it’s as ugly as Northern New Mexico can be pretty. We drive through endless dried-out plains with grey shrubs and a brown horizon that melts into a dark, cloudy sky. A billboard with an iPhone that shows Jesus and the slogan don’t ignore Jesus when he calls you becomes my memory of Northern Texas.
Northern New Mexico is an incredibly wide, gradually ascending terrain that makes me think of Western movies and Native American hunters on horses. As we arrive in Santa Fe (7,200 feet altitude), we realize how much the American Native’s tradition is woven into the local style of living. For the first time on this trip, I find myself thinking that I could spend the winter here. It’s not a warm place, but you can ski, it has a slow pace of living, enjoyed by a large community from everywhere in the country, just like Boulder. Too bad that a place like Santa Fe attracts mainly older and wealthy people who have turned it into a tasteful version of Disneyland, depriving it of authenticity — and decent housing below $5mn.
The next day, on the way to Scottsdale, we drive through Flagstaff (6,909ft high and with the 12,600ft high Humphrey’s Peak as a spectacular backdrop), which I remember from a night at an RV trailer park with my sons in 2006. Against my expectation, I like the place (another Boulder-esque town), and my mind is briefly considering the potential circumstances of living here. These places seem to have something in common: a crowd of hip looking young people, great coffee shops with excellent espresso, reliable high-speed internet, healthy food, clean streets, plenty of dogs and a tolerant culture. The problem of living in such places is that they have no or only bad flight connections to the rest of the world. These are the people who arrive in Chicago O’Hare with me, after a 9-hour flight from Europe, missing their connecting flights to end up at some dingy airport hotel for the night.
From Scottsdale — a pleasant but unremarkable retreat for retirees and sales conference attendees— we embark on our last stretch of the trip. In the middle of the desert, the agglomeration of Palm Springs appears like the ancient fertile lands of Mesopotamia, as we descend from the mountains. It depends entirely on artificial irrigation and water that comes from either a mile deep in the ground or imports. It is a strange phenomenon that the fastest growing cities in the US are all deeply deprived of natural water resources. Their end has been predicted many times for almost 50 years, but people find ways to postpone it.
Finally, we hit the outer suburbs of Los Angeles. Traffic density and aggressive driving are increasing. After 6 days of tranquil cruising, I am not used to this anymore, and I am beginning to doubt my suitability for the big city. A billboard pops up to the side of the highway, asking who killed Jesus Martinez? Call us, if you know something! We have arrived in this dizzying, sprawling town, the only true metropolis other than New York City. I think I can love this place, and we will work from here for the next month, hoping that the worst of winter has passed by the time we return to Chicago. In the evening, a check of our iPhones tells us that the next 7 days will bring a winter storm with rain and temperatures as low as 39 degrees to L.A.. We figure out how to turn on the heat in our house, and we unpack the jackets that we brought with us, hoping we wouldn’t need them. Life can be unfair.
