Being the paragon of enlightenment that I am, I’ve written a grand total of two articles reflecting on years past.

One was 19 lessons I learned in 2019, which was like 15 lessons too long to be digestible. Another was Some Random Dude’s Top 10 Books of 2017 which, though technically accurate, made it sound like I read far more than 10 books that year and need to cull my list like it’s the damn Pulitzer Prize.

(What happened in 2018, you ask? I am not sure. Probably not much).

But today is the last day of 2020. And it seems only right to reflect on this unusual year in an unusual way.

So here goes.

8 Things I Didn’t Learn in 2020

1. How to stay cool, calm and collected through a global pandemic

I shot into 2020 roaring with excitement, gliding on the high that comes with discovering the promise of freelance life, like it’s some secret the universe (or, at least, most educational institutions) have tucked into the far corner of the pantry.

Until that point, I worked hard to design a life that reflected my values — cementing healthy habits, meditating daily, writing consistently, checking off travel dreams, working for myself, seeing my family often.

Then the ‘Rona came around and my parents’ favorite Yiddish saying about God hearing our plans and laughing hit hard.

I didn’t feel its impact right away. It was like those grainy videos of nuclear tests where you see the cloud from afar before its shockwave rocks the camera. Worse than the shockwave, though, was the radiation that remained in its wake: an ambient anxiety, a dull noise that seeped into every activity and every decision.

So, like many of us, I spent much of 2020 appearing strong for others while being anything but inside. Within, a cloudy chaos swirled — borne of anxiety, fear, sadness. I couldn’t admit to it lest I shatter the image of the totally cool, calm, collected guy I worked so hard to cultivate.

But the truth is I wasn’t that guy. I am not that guy. I didn’t learn how to be totally OK with a vastly uncertain future. I didn’t learn how to remain resolutely confident in my decisions when the ground is shifting.

Maybe that’s ok.

2. How to react when a coworker’s child hogs the Zoom during an important call

Yeah, I haven’t figured that out either.

Do I awkwardly wave at the child? Do I wait for her to leave? 

Do I keep walking through the spreadsheet while she pours ink on her parent’s keyboard?

Much to think about.

3. What it’s like to work for yourself, long-term

There’s a book called Designing Your Life that talks about creating test pilots in your own life to validate hypotheses about what you think will make you happy. Try-living-in-the-suburbs-for-a-month-before-moving-there, kinda thing. We rarely consider this, but our notions of what will bring us joy rarely match reality.

So I wanted to use 2020 to test an important hypothesis: I’d enjoy running a low-key lifestyle business while spending the majority of my waking hours pursuing non-work passions, like writing.

I started an operational consulting business in late 2019 and absolutely loved the freedom it afforded me, and the variety of clients I got to work with. It felt pretty good. But I also traveled a lot, and worked no more than I needed to pay the bills which wasn’t representative of how that lifestyle looks long-term.

In mid March, with NYC locking down and the virus spreading uncontrollably, many of my clients put my work on hold. Instead of looking for new clients, I chose what felt right, which was to commit to a major project with Cityblock Health to provide ER-level care right in the homes of Medicaid and Medicare members. It quickly turned into a full-time job. 

Because my time working for myself was so short, I still don’t know if it’s a lifestyle I’d like long-term, which was one of my goals for 2020. 

I’ll have to save it for another time, I guess.

4. How to grieve in a digital world

He’s a Jew?! But he’s a good man!

that, according to family lore, is how many grandpa Tima’s Soviet colleagues responded when they found out his ethnicity. My Deda Tima spent his early years in a remote part of Kazakhstan to escape the Nazi onslaught and his middle years proving his worth as an engineer and director of a major manufacturing plant in Soviet Ukraine.

In the final chapter of his life, he moved to the US, quietly, humbly. Him and his wife Sofia settled into a one-bedroom retirement community near San Jose, California. But here his career as a community activist was only beginning, at the spritely age of 70. He served as the chairman of the Russian-speaking WWII veterans association for more than a dozen years, organizing road trips to important monuments, raising money, even starting a choir that sang wartime anthems (despite not being, err, known for his vocal range).

He tried to step down from his position a few years ago but the organizing committee members refused to accept his resignation. So he marched on, sending me newspaper clippings along the way from Russian-language tabloids covering their latest choir recital or fundraiser. I still have a whole folder of them in my room.

My Deda Tima passed this year, after a few weeks in quarantine. He died of heart failure, which is how some poets refer to loneliness.

I haven’t figured out how to grieve for him, or others, in this digital world. In a world of awkward Zoom funerals and casual FaceTimes. You talk for a bit, exchange memories, a couple of laughs, maybe. Normally, the silence puts things where they’re supposed to be. But with a digital world comes a digital silence, which is too easy to break by hanging up and teleporting back to our usual worries. It will be a while before we learn how to get closure this way. Our souls yearn for analog hugs and analog jokes and analog silence.

But because I wasn’t there when he left and couldn’t come bid farewell, I get to freeze him in a scene of my choosing. So I like to imagine him now, marshaling a squad of ex-Soviet octogenarians as they amble across the Golden Gate Bridge, having lost their way to the kosher deli that would serve them lunch. Most clutch their windbreakers and bucket hats against the wind but Deda Tima just raises his arms and looks up at the sky. So much life. Such plentitude. Are you guys seeing this? He has to yell this because his hearing aids don’t work well and he wants the world to hear.

I laugh at that image and in it, feel joy that he got to spend so much time with us on earth. I love you, Deda Tima.

5. How to write consistently while working full time

I started the year strong, launching my blog and consistently publishing a long-form piece per month, which was my original goal. I wrote about how we can use the psychology of lotteries for good, why caring about things will go mainstream in the 2020s, and what the future of social media holds.

But building a writing habit is a bit like building an elaborate sand castle. It takes a lot of time and patience, and can be undone in seconds by some unsupervised kid with spiked hair and Billabong shorts and no one to model kindness.

Any disruption to the daily routine can undo a painstakingly built writing habit, like a vacation or a new job or, I guess, a global pandemic. As I dove into my new healthcare project in the middle of a global pandemic, I haven’t learned to balance the responsibilities of a full-time job and the discipline required to write consistently. I wrote intermittently, when inspiration struck, which is no way to write.

If I am serious about growing as a writer, I would like to keep showing up, even (especially!) when it’s easier not to.

6. Whether it’s OK to go to that thing or not

What a cluster. In my social circle, there won’t be a history of COVID, there will be histories of it. The ways of life of friends and relatives living during COVID ran the gamut from “See you in 2022, call me sometime” to underground wall-to-wall raves deep in Brooklyn.

It was a rational decision maker’s nightmare. There were:

• Rapidly changing ground truths as we learned more about the virus

• Contradictory advice from different public health institutions and impressive-sounding experts

• Frequently changing advice from the same public health institutions (remember when the WHO advised against wearing masks?)

• Journalists suddenly becoming public health experts and confidently spewing unconfirmed opinions as truths

• Friends and relatives suddenly becoming public health experts and confidently spewing unconfirmed opinions as truths

• Completely unique risk profiles (and therefore action plans) for every person depending not only on their unique health factors, but on the health factors of those they plan to see or be around

My partner and I tried to create a strict rules-based framework for what we choose to do or not do. That was damn hard. We ended up either too conservative, only to be drawn out to dinners and social hangs by the FOMO of Instagram and the revival NYC saw in the summer, or too liberal, drawn back indoors by the news of a relative’s death, or some fear-laced headline.

With so much contradictory information and such a range of attitudes around us, we could never figure out what the “right” approach was, and that was freaking tiring.

7. How to separate work from life when working from home

Many things in life are a matter of perspective. What I call “my office”, my girlfriend defines as “her closet”. And so I dig through spreadsheets and make smart-sounding statements on Slack mobbed by satin dresses and silk pajamas.

And from that cavernous lair I emerge into “our kitchen”, a zone my partner has baptized “her office” (although this honor sometimes belongs to the bed too). With both of us working remote, and all over a tiny Manhattan apartment, I haven’t really learned how to separate my work life from my non-work life.

As such, I find myself responding to emails at all hours of the day and, worse, constantly ruminating on work problems long after I close my laptop. Like many others, we were thrown into remote work, and I’ve been focused more on resolving the work part than the remote part.

8. Why my girlfriend’s dog likes to scratch the wall near my shoes

I asked him. No luck.

Happy new year, friends. Congrats on getting through it.