2021

Alex Schiff
16 min readJan 9, 2022

“As if Nature had intended to make a gorilla, and had changed its mind at the last moment” — The Code of the Woosters, P.G. Wodehouse

Last December, I claimed that 2020 would not formally end until March 2021. I hate when I am correct in ways that forecast doom, but correct I was. Fortunately, when 2021 finally began, it was pretty solid — except for 2020’s shitty low-budget sequel, December 2021.

Part IV: Late-Late-Mid Plague

“There are moments, Jeeves, when one asks oneself, ‘Do trousers matter?’”

“The mood will pass, sir.” — The Code of the Woosters, P.G. Wodehouse

We left off in Late-Mid Plague, and January was more or less indistinguishable from December, besides that nearly everything was worse. We had a stupid coup. Nationwide COVID deaths were surging to new levels. My parents briefly considered buying a fixer-upper in rural Vermont. Shit was bleak, and mostly nothing happened.

Mood, January 2021

“We got through Christmas and New Year’s uneventfully, and are waiting for one more green light from the doctors before I can take them back to Florida.” — 2020’s reflections

Eventually — 11 months after my accidental Michigan saga began and 4 months after my dad’s kidney transplant — that green light came. This was the terminus we were waiting for. When we were no longer stuck. When discussing next steps was no longer followed by “at some point,” pending something out of our control. When, after several false starts, we could give our brains the freedom to think about what’s next.

In their fervor to get back to living, my parents had determined that the lives they had left behind in Florida were no longer there. And they were not. My mom spent months getting yelled at by her clients for wearing a mask and watching her friends pretend that the “China virus” wasn’t real. My dad hadn’t been home since February 2019. Florida was different and they were different. They sold their house and, after considering pretty much every state with legal weed, bought a new house in Tucson shortly before we left Michigan.

Not featured: the additional bags that had to sit on people’s laps for 2 days straight.

By the first week of February, my parents, Tamar, and I had packed a van to the ceiling and were on our way to Florida. From what I remember, it was the worst road trip I’ve ever taken, and I have no positive memories of the experience. I say “from what I remember” because I blacked out at some point between southern Kentucky and northern Tennessee and don’t remember much after. I don’t know if it was the rain, the clashing neuroses in the vehicle, or the imminent mortality risks posed by every food and bathroom stop. But mentally, I was lying on a beach in Sardinia.

I would like to say that February was better. It was not. The details of why those 30 days were terrible are uninteresting, besides that apparently every letter I ever wrote to the tooth fairy was preserved, along with my letter to “T.V. Co” asking why they restarted the Trunks Saga instead of starting the Buu Saga. Otherwise, I spent most of that time in Sardinia and honed my ability to compartmentalize.

My time in Tarpon Springs did give me three things: tolerable Greek food, weather nice enough for long walks, and a different vantage point on what was very much still 2020. Florida had gone full Trump, and “Stop The Steal” demonstrations were common on routes known to me as how I got to high school. Metro Detroit wasn’t the best about COVID safety, but Florida had quite clearly decided that its pandemic strategy would be “YOLO.” Through cracked windows and masked walks, I spent every single day in Florida feeling gaslit and dissonant.

In early March, we left for Arizona — the (good God I hope) final destination in the long journey of my dad’s recovery. This road trip was also terrible, for largely the same reasons, with the added bonus that the width of Texas is unholy. I did get to see a few new places in a year that was utterly absent novelty, so I rate the experience one star instead of negative infinity points.

Good on you for committing, Roswell.
White Sands National Park!

My parents (and their close friend) are now settled in Tucson, rebuilding their lives just like all of us. My dad’s recovery has continued to be uneven, but his kidney is still going strong and he’s entering 2022 on an upward trajectory physically, mentally, and emotionally. When I spoke to my parents on New Year’s Eve, we talked about flooring. Heading into 2021, I would have given absolutely anything for our most pressing topic to be flooring. I can not overstate my desire to see them happy and achieve peace.

V: Early Late Plague

“Time rarely weighed upon him, for he had many methods of passing it.” — In Cold Blood, Truman Capote

For the first time since February 2020, there was not another checkpoint to get through to ensure survival. There was just the hard work of figuring out normal, and I needed to figure out mine. I got a haircut — my first in about the same timespan — and hit the road to California, where I was making a stop in LA to bubble with one of my closest friends before the next waypoint with Tamar’s family in Sacramento (where she had already flown ahead, wisely avoiding the second road trip).

“How is the drive?” -> “SOBBING SOBBING OPENLY SOBBING”

I could have cried on that drive into California. Greenery seemed to appear as soon as I crossed the border from Arizona. The golden hour greeted me as I drove through the mountains outside Palm Springs, and I could not help but stop my car to take photos more than once. I had nothing but time to reflect on my Before Times life driving up and down and across this state every weekend I could.

This was the very first time I had chosen to be anywhere since February 2020, and while COVID was not over, I felt very palpably at that precise moment that the worst part was behind me.

Late March is when 2021 began for me, because it’s when it felt like the trendline turned upward. I had access to great hikes, not aimless walks through suburban streets, used car dealerships, and boarded up businesses. For the first time since the previous summer, I had places I both wanted to and could go. I actually hung out with a friend — around a table, eating and drinking and talking and remembering how to be human beings. I ate in a restaurant (still outside) and very likely did cry. I got vaccinated the very moment I could, and spent the waiting period for protection to kick in pacing and ranting “I will NOT be Tarrou! I will NOT!

“What did you do in LA?” -> “SOBBING SOBBING OPENLY SOBBING”

After that, it felt like I was “done” — I had survived war. It was time to survey the wreckage.

That’s exactly what it felt like returning to San Francisco, where I had lived for nearly five years before the pandemic, for two brief stints in April. SoMa felt like a scene post-rapture, with not a soul on the streets except the occasional heathen and discarded clothing left behind. My old work neighborhood haunts were elated to see a familiar face, but they wore a deep weariness on theirs. The office building I spent the better part of five years in was fully empty on a Friday. The only part of the Financial District or SoMa that had any life were the parts being taken over by the Tenderloin — which was now a regular slum, rather than a slum people pretend doesn’t exist on their way somewhere else.

By contrast, the more residential areas — Potrero Hill, Marina, Pacific Heights, Duboce Triangle, Noe Valley — were having a renaissance. The wealthy tech workers who used to spend mealtimes in SoMa or the South Bay now spent their time and money in their own neighborhoods. Outdoor dining had brought energy to streets that used to be muted — but this is still San Francisco, so the energy was still suffocatingly one-dimensional, mostly male, and mostly talking about tech.

Here was the “pandemic exacerbates existing trends and inequalities” theme I had been reading about through a screen, I suppose.

The wig didn’t make the cut in the rapture, I guess.

Having kept regular contact with less than a dozen people through 2020, reconnecting with people in-person during this period was also the first time I began to take stock of how different the pandemic experience had been even amongst my friends. In my liberal bubble, no one dared say they lived life as normally as they could get away with, lest ye be crucified on the altar of the common good. Everyone was “safe,” but that sometimes meant similar experiences to my own, sometimes it meant outdoor dining, sometimes it meant vacationing in Florida, and sometimes it meant proceeding with weddings and bachelor parties but still wearing a mask when grocery shopping. Sometimes it made me feel pangs of regret, like I over-corrected and last year didn’t have to be so bad. Sometimes it made me feel dissonant, like I had to reconcile my friendship with their actions in 2020.

It was also my first glimpse into how uneven and murky “done” would be, as unlike wars, pandemics don’t have cease-fires. Some people, like me, went back to something resembling normal soon after being fully vaccinated. Others re-emerged anxiously, and others never emerged at all. But what if it was really crowded? What about basketball games or concerts or even conferences? What about hanging out with someone who isn’t vaccinated — which seemed fine in late April when I was “ahead” of some friends, but somehow felt risky when it was their choice? Did delta really change the game if you were vaccinated?

And just as we were getting vaccinated in the US, many work colleagues in other countries were going through their worst periods. One of my colleagues — even younger than I — passed away within a week of my second dose.

Part VI: Mid-Late Plague

“What is this bazaar, this souk, this mess, this conglomerate of barbarisms, this empire of signs, this chatter, this fall to the lowlands of belles-lettres, what are these backyard cackling, is it serious this thing, it starts with where, it ends with where, damn it.” — Broken Glass, Alain Mabanckou

Just before the pandemic, Tamar and I had decided that we were going to move to New York. 2020 obviously had other plans, but through all the ambiguity, that remained a sort of hedged rally point for our future. After a year of “probably,” we finally made the move shortly after our second dose, and we found our way to our first apartment lease — our first together — in June.

Hello New York!

I have never feared moving cities. I have moved cities 6 times, and have long said that my biggest anxiety in any move is finding a new person to cut my hair. I’m not attached to very many belongings, you can make friends and find activities anywhere, and, unless you are moving to Florida, it’s never going to be as bad as moving to Florida. All my moves were also driven by external factors — college, an accelerator program, a job.

This move felt unique. First, it was my first move to be in a place for that place. When friends asked what brought me to New York, I simply responded, “It’s the greatest city in the world.” Because it is, and that’s the only reason you should need to move to a place.

Second, this move was a reassertion of agency (for both Tamar and myself, though for different reasons). I started to become disenchanted with San Francisco in 2018, and I was not happy living there by 2019. One of my best friends had moved away, and an era marked by having lots of interconnected friends with common interests had faded into an era of disconnected yet similar-feeling relationships. The rah-rah change-the-world kool aid of my early 20’s — the kool aid San Francisco increasingly felt built on — slowly evolved into a more impatient pragmatism by my late 20’s and early 30’s. I had gotten back into reading, and that reminded me that the world was big and complex and there were more conversations to be had than the ones I felt like I had been having. Maybe it was my dad getting sick taking its toll, or any number of work circumstances. Maybe it was just feeling like I had done what there was for me to do in San Francisco, and I had run out of weekend trips to sedate that feeling.

It was likely all of that, but I can pinpoint that by July 2019 I had begun to feel I had overstayed my welcome in the life I was living. Like I was becoming a ghost living in the echos of a life I had outgrown. Circumstances alone (some valid, some not) kept me there until circumstances kept me elsewhere.

Moving to New York was my first act of rebuilding the life I wanted from the wreckage of 2020, and that first summer was one of relief. Where my life in San Francisco was marked by itchy feet, the idea of being anywhere besides where I was now felt unfathomable. I was, for the first time in many years, where I was supposed to be.

I will take this over used car dealerships and barbed wire fences, even if I can’t find decent Mexican food.

That summer was also marked by wandering. Wandering through neighborhoods and looking at the architecture, wandering from cafe to cafe with my book, wandering through the Met, wandering around Coney Island or Brighton Beach, wandering up and down the Brooklyn Heights promenade, wandering through parks, letting my mind wander. Sometimes there was a destination, but it was hardly ever the point. Wandering was the point, punctuated by eating, drinking, people-watching, or reading.

Unlike in my return to San Francisco, where I was catching up with friends after a roughly yearlong hiatus, I was now catching up with friends that I hadn’t seen in many years or meeting new people entirely, whose lives had taken much more diverging shapes. In several cases, people were just leaving under pretenses inverse to my arrival — they spent the worst year of their life there, and in order to move on they needed to move anywhere else. Some had kids, and some were doggedly committed to the opposite. Some had switched careers entirely, and others were just hitting their stride in their field. Some had made a ton of money, and others had not. I forgot how much I need contrast in my life. That contrast makes it easier to understand yourself, and play out variants your life could take without having to live them first.

This summer was also marked by learning what parts of “2020 life” I would take with me, and what parts I would not.

I remember thinking clearly during 2020: I can’t believe how much money I saved by not going out to eat or drink! Why would I go back to eating out just as an activity, instead of because I wanted to go to that restaurant or bar? This was an obvious farce. I went right back to old habits. Frankly, I over-corrected, because I so desperately missed being out in the world.

(And because in New York, “restaurants and bars I want to go to” is a list that just gets bigger every day.)

The same is true of virtual happy hours. Once my only method of human interaction, they seemed like a great way of staying in touch with close friends in faraway places post-pandemic. After a year+ on Zoom and Google Meet, it seems that it has gone back to being a work and catch-up thing, vs. preferred for any ongoing socializing.

What I did keep:

  • Books. I read more books (real physical books, not audiobooks as I used to listen to) in 2021 than I read in 2020, and I read more books in 2020 than 2019. I read more now in New York than I did anywhere else, so I hope to read more books in 2022 than 2021.
  • Curating my information diet. Still no Facebook for me, aside from point uses like events or messaging. I’ve made progress diversifying my Twitter feed and news sources, but I admittedly still spend too much time on both, and plan to spend less time there in 2022. There are both better ways to be informed and better ways to be entertained.
  • Donating money. It felt like 2020 surfaced any number of urgent causes, and made it obvious that supporting them financially went further than showing up to a rally. I was no major philanthropist, but I did continue to set aside money for things that were either personally meaningful (the American Kidney Fund), local (Brooklyn food pantries and Afghan refugee resettlement in New York State), or impactful (various health-related programs recommended by GiveWell).
  • Investing in quality clothing. My best investment in 2020 was a pair of thick socks. My best investment in 2021 was a fall jacket, as part of a general “detox” of my San Francisco->pandemic wardrobe.
  • Shirazi salad, scrambled eggs, brie cheese, lox, turkey, spinach, and zaatar. I certainly can’t say any of these are new, but I do feel like the increase in my consumption of them has persisted beyond pre-pandemic levels.

Surveyed from the jostling for normalcy through the summer, it was also easy to see what I had lost: trust.

To preserve my physical health and that of my loved ones, I’ve had to become skeptical of CDC and public health recommendations (remember “only get a booster if you’re at-risk”?). To preserve my mental health, I’ve had to become skeptical of journalists, lest I develop a myopic and limiting view about things like vaccine hesitancy (it’s not just Trump supporters). To preserve my emotional health, I’ve had to compartmentalize or cut relationships, like a soldier returning home after witnessing how their comrades behaved in battle. Without trust, it’s hard to feel confident. Without confidence, it’s hard to ward off anxiety. When you’re anxious, everything sucks and feels unsolvable.

And that’s the shitty truth: most of us were traumatized by the pandemic in one form or another, and we’ll leave it with our own triggers and work to do. No wonder we all ended up with animals.

It’s cheaper than therapy…as long as you don’t run the cost comparison.

Part VII: Late-Late Plague

“Yes, man is mortal, but that would be only half the trouble. The worst of it is that he’s sometimes unexpectedly mortal — there’s the trick!” — Master and Margarita, Mikhail Bulgakov

In spirit, Summer 2021 (and Mid-Late Plague) lasted until mid-November. The weather became chillier, but I bought a jacket, and my day-to-day life was not very different. I still spent most of my days wandering around outside, and COVID felt more like a logistical challenge than a present threat to my safety or limiting factor.

It was around this time that I ended my 6.5 year run at Occipital in the most 2020–21 way possible: I sent a Slack message asking, “So do I sign out of Slack now?” I moved across the country to start this job in early 2015, and in leaving it, I simply shut my laptop and went to pick up my laundry.

6.5 years is longer than I’ve done…basically anything. It was time. I had achieved what I joined the company to do, the founders I joined the company to work with were no longer there, and I had felt for some time like I was simply “doing more” vs. learning and growing my skills. By now, the product has escape velocity, and there were other leaders to whom I could pass the baton. For the first time in my life, I had created something that had staying power beyond me, and I’m still phenomenally supportive and bullish on the success of Canvas.

“Reset and rebuild” was the theme of 2021, after all, and it was to take no prisoners.

I joined Square the week after Thanksgiving. Keeping with the theme of change, I wanted to try a big company after a decade grinding it out at startups. Square ended up being the right fit based on my team’s focus on help experiences — I had something unique to offer as a product manager who had also managed a customer success team, and I wanted to optimize for the impact I felt I could make. Who knows if I’ll like BigCo life a year from now, but after a month and change I at least feel optimistic about the impact I can make.

And then.

Thanksgiving is also when COVID transformed back into a present threat, again. The first variant with meaningful immune escape appeared, and predictably, again, we did mostly nothing until it was too late to do anything (though it’s debatable what there was to do besides build up test capacity). We found ourselves running risk calculations on everyday decisions, again, and changing travel plans, again, as COVID took over New York, again. We made it to Sacramento before things really exploded, and then, again, it spread everywhere else. Eventually, again, I found myself quarantined somewhere I didn’t expect to be.

This time, we fucking did get COVID. Can you tell my throat wasn’t the only thing that was sore?

After two years of prevention jiu-jitsu, and two years of constant background anxiety, our Christmas bubble was popped, and we spent the last seconds of 2021 similar to the first: through a screen, on quarantine. Likely thanks to being recently boosted and/or omicron supposedly being less severe, it was unpleasant, but fine.

View from Quarantine, The Sequel, when we tested positive on “vacation” in Lake County

My goal for 2022 is to be able to look back at the worst part of this saga as unpleasant, but fine.

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Alex Schiff

Product @Square. Prior: built Canvas @occipital, co-founder @Fetchnotes, VP @Benzinga, and chief opinionator @michigandaily.