Getting “real” and creating the future we want - my pandemic reassessment

How I changed jobs, quit Facebook and Instagram and learned to love being a remote worker in NYC.

I look at the pictures on my phone from February and March of 2020 more often than I should. I scroll through the last days of normalcy, from shows at Lincoln Center when Covid was already quietly circulating, on to pictures of empty grocery shelves, then long outdoor queues, mask selfies and empty avenues. By late March, the camera roll is full of 1000 piece puzzles and rooftop videos of the 7 PM cheering across the Upper West Side.?

The other night I was waiting for a delivery and lingered on pictures of me and my son Nathan from one of our regular late day "shutdown" walks in the North Woods of Central Park. We tried our best, in the early days, to treat it like an adventure. He was part way through sixth grade - barely out of elementary school - and it was easy to get him back outside to explore the hills, giant rocks and abandoned structures of that part of the Park. I was gut-punched by how much he had grown in two years.?

I think about the unfolding of the pandemic two years ago, but also about this time last year. When the one-year mark of the pandemic approached in early 2021, we were in a dark place. A year of remote school and ballet instruction had left Nathan always online, but disconnected, disengaged and cynical. His grades slid and he wanted to quit ballet. My wife Amy and I were exhausted, stuck in the time loop with him. We couldn’t bring our best to him or our jobs.

I tried to be optimistic, I wanted very much to think we were leaving behind the raging dumpster fire of 2020. Vaccines were coming. The end of the pandemic and the start of the Roaring 20’s were upon us, supposedly. The political discourse might finally chill. After a year when the world spun off its axis and knocked us off our feet, I needed a revival, a clear way out and forward. Puzzles, walks in the parks and baking adventures could no longer sustain my family.

But that optimism was already taking hits - from the shock and aftermath of January 6 and then repeated blows from the successive waves of Covid and the escalating, polarized battles over everything from masks and vaccine mandates, to the teaching of history in schools. Social media fanning the flames of all of it.?

The reality is that if 2020 was the year that changed everything, the second year of the pandemic emerged as one of halting renewal and the dawning realization that even the near future was getting harder to predict and impossible to control. We were taking two steps forward and three steps back and to the side. To get myself and my family unstuck, I realized I had to work actively to start creating our “post-pandemic” future, joining, it turned out, millions of others propelled by the same currents who reassessed their lives and quit jobs, moved or both.

There’s a reason they tell parents to put on their oxygen masks first on planes: you can’t help your family if you run out of air first. I started 2021 by focusing a bit more on myself, being more intentional with my time; a little more sleep, a little more exercise, less time online and a concerted effort to read more (books - actual books from trees). I didn’t read as much as I did before smartphones, or when I used to actually get on planes (and if I am being really honest, before planes had reliable WiFi). But way more than 2020, which was defined by 12 + hour workdays and too much late night doomscrolling. Putting the phone away and taking the time to be thoughtful about what I was reading kept me from spiraling with the news cycle and helped put the current moment in context. Here is my reading list (with reviews).

Ultimately, I entirely quit Facebook and Instagram, partly as an ethical stand, but mostly because I decided they could not have any more of my time, attention or creative output. It led me to spend a month organizing 20 years of photos and settling on a new channel for my photography, presented as I wanted to be seen, unmolested by bullshit algorithms.? I have a whole separate post about it coming, if you want to suffer through some serious virtue-signaling.

Moving, as I am led to believe literally everyone did, was out of the question. We love NYC and happened to be living in an apartment we had bought, in a twist of almost tragicomic fortune, the day NYC shut down. A six month delay moving into our “forever home,” while people were writing obituaries for New York had left us nearly paralyzed with stress over the summer and fall of 2020. But it was where we wanted to be, and once settled in, I was left only to consider how and where I wanted to work.

Though we really loved the new apartment, I decided I could not and would not work from home any longer. I could not pretend to be buttoned-up and locked in on Zoom when everything else was on fire on the other side of the door. We were done. I needed to work outside the apartment, but NYC and anyone wanting to work in an office faced strong headwinds from the seismic acceleration and normalization of remote work during the past year.

By late last winter, I had more confidence in the type of work I wanted to do. I wanted to create products from the ground up and help build a company where I could bring my whole self to work. I wanted some of the flexibility this new paradigm afforded, but wanted to be with an organization where I knew everyone and they knew who I was. This meant a startup. For the second time in ten years, Kristy McCann Flynn was ready with the opportunity that would change the course of everything.?

The only problem was that her company, GoCoach was fully remote.

The long path to GoCoach

When Kristy first told me four years ago that GoCoach was going to always be remote, I thought “Sorry… that’s not for me. Good luck.” I’ve long loved going to an office and only worked from home sparingly.?

I even took a job in late 2019 with Success Academy Charter Schools that offered me an analog experience that was facing extinction: working with all my colleagues in one central office. I doubled-down on my love of New York with a chance to make a more direct impact on families in the city. After years of working for distributed companies and suffering their stumbling attempts to adjust culture to distributed work at scale, I wanted all-in on in-person. It was great, and it lasted roughly three months, until March 13, 2020.

With the job losses endured by millions and the personal risk faced by frontline workers in 2020, working from home was a privilege I was afforded as a knowledge worker. I was fortunate. I know that. And yet… Working from home for over a year was still a personal nightmare I don’t want to revisit. I felt like Schrodinger's Cat: both alive and dead… both at work and at home at the same time as the barriers between work, home and school collapsed inside the walls of a two bedroom apartment.?

My home office set up for the first six months working from home was an outdoor cafe table in a corner of my son's bedroom.

What my family endured was not worse than the typical experience for any working parents who had the privilege to continue working from home, but that did not make it any less awful, day in and day out. Our son had 15 months of remote schooling while we managed the stress of being present and engaged for our colleagues while present and engaged for him. Too often, both efforts failed. But the pandemic work/home/remote school experience we shared with so many was also compounded by the fear and grief that the life we had in NYC - and still wanted - might not come back anytime soon.

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I’d been in NYC since 2012, when I moved from Boston with my wife Amy and Nathan, who was 3 ? and a rising pre-schooler. We lived in the city and nobody we knew with kids was planning to stay. Faced with a seemingly inevitable move to the suburbs along with our friends, we zigged when most zagged, opting for complexity, uncertainty and opportunity, settling in the most densely populated, expensive place in the country to raise our child as he began school.?

Amy had long wanted to move to New York. I was ambivalent, but promised I’d be open to it if the opportunity arose. Kristy was my HR Business Partner at Pearson at the time and the one who gave the push and made it happen. A year prior she had gotten me an executive coach, Frank Traditi, who helped me envision what kind of opportunities and challenges I wanted to help me grow. The opportunity came in the spring of 2012 with the newly formed Pearson K-12 Technology Group in New York City. After only a few weeks of discussion, and a kick in the pants from Kristy, we had our place on the market and never looked back. Our friends and family viewed our move to NYC with an equal mixture of grave concern and envy.

We didn’t disrupt our lives like that because it seemed like an easy way out of a future in Boston that not longer excited us. We couldn’t embrace the conventional narratives that should have landed us in the suburbs or the sunbelt, where our parents had settled, or our son in private school. We did it for the challenge, and the sense that we were creating opportunities for all of us that we could not find anywhere else.

We spent the next eight years slowly and deeply falling in love with the city. The kind of love that is not without its fights and perilous moments. Full of setbacks and “pinch me” moments. Being trapped in an un-airconditioned subway car in the near embrace of a sweaty stranger will make anyone, at least for a moment, doubt New York is worth it. But it was. Our personal and professional networks grew in curious and unexpected ways. I ran and biked all over Manhattan. My wife, who worked remotely for clients back in Boston, tap dances and became a regular alongside Rockettes and aspiring actresses in the gritty rehearsal studios in midtown. We saw countless Broadway shows and met Broadway stars. Nathan got the performing bug and filmed some commercials and a movie that took him across the city and eventually to a premier at SXSW in 2019. He danced with Alvin Ailey and New York City Ballet, performing in Ailey’s Revelations and NYCB’s Nutcracker and Swan Lake before sold out houses in Lincoln Center. We now know that Covid arrived in NYC during that Swan Lake run in February of 2020, quietly circulating and then exploding in March, suddenly relegating the life we had to the past, seemingly unlikely to ever return.?

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The pandemic experiences of millions of others were far different, of course. Many faced unemployment, sickness and daily risk to do their jobs. Then the labor demand as the economy turned around gave frontline workers more leverage, leading to higher wages. Professional workers traded soul-crushing commutes for work-from-home arrangements that provided space, fresh air and time with friends and family, leading to epiphanies that this should be permanent and optional, not temporary and forced. Liberated by Zoom and Slack, they relocated far outside city centers or went full digital nomad. The size of this shift may be overstated in the media narrative, but we all know people who did it. For me, this macro change was not just personally discomfiting, it loomed like an existential threat to the economy and real estate of New York City. As a committed New York resident and apartment owner, I possess a fierce economic interest in people going back to offices, making me a cheerleader for the office-industrial complex. When people can work anywhere, the economics and attractiveness of office density collapse. And working from home in NYC seems like a uniquely stupid financial equation.?

After an unquestionably bleak spring and summer of 2020, evidence of life in NYC started to emerge that fall and winter, even as Covid surged back. Families had returned for school, masked up in the parks in the evening after days on Zoom. The city was still without its lifeblood - office workers, tourism and the arts -? but it became obvious that not exactly everyone moved (and many were moving back). Too many people were enduring frigid outdoor dining. The sledding hills were too crowded. The parks were full of runners and bikers on breaks from their workdays. Too many people like me, waiting for spring and vaccines. I stopped resenting coworkers who appeared on Zoom from the mountains or beach. I came to absorb how transformative the moment was for resetting the balance between employees and employers, work and family. I stopped feeling sorry for myself. By digging our heels in New York, we might be zagging again when it seemed everyone else was zigging, but it was all part of the same reset and reevaluation of priorities.

Kristy had approached me about GoCoach several times the past few years, and by the spring of 2021, my next move was a no-brainer. I wanted finally, urgently to join her and Rebecca Taylor at GoCoach and be a part of what they were doing to support employees in their growth at this remarkable moment in history. Kristy, Rebecca and their growing network of coaches and advisors had kept GoCoach afloat during the darkest days of the spring of 2020, then grew it as companies came to realize what a powerful offering GoCoach had for their employees. I wanted to join them in building a company grounded in creating the very kind of personal, human-centered learning so desperately needed as we emerged from the pandemic. That motivation far outstripped my aversion to working remotely. They were ahead of the curve, ready for this moment. I was all-in. I just needed to make working permanently remote work for me.

Becoming a remote worker by choice, in the greatest city in the world

Since April, when Success Academies re-opened their office, I had been back out of the house four to five days per week and fell in love again with parts of the city I had not visited in over a year. The separation of home and office again was not only healthy for me and my family, but proved vital. And I was part of a slow, but inspiring re-awakening of the city. But when I was ready to start at GoCoach in July, I still had no idea what I was going to do. So the night of July 4th, I signed up for a one month free trial with WeWork, who managed to survive their collapse and hang on to a seemingly endless array of locations across the city. I showed up the next day at their Bryant Park location, but with no badge, I couldn’t get in because it was… a national holiday. Unwilling to accept defeat and return home, I set up shop in Bryant Park, moving around to find shade and power in Whole Foods and a coffee shop. Life as a remote worker had begun.

My "office" for my first day at GoCoach.

The rest of the month, I tested out locations all over Manhattan, trying different commutes, vibes and amenities. I had my favorites and a few I never visited again. Staffed with skeleton crews, and stripped of their notorious kegs, I still dug the energy and activity in the common areas (less so by the bros sleeping on the couches - potential inspiration for an Instagram account). People were meeting again, in person. Maskless!? But I’d swipe my badge to leave the common areas and find a stark reality: floor after floor of dark, empty private offices cleaned and ready for teams whose return seemed far from imminent. When Covid cases edged back up as Delta emerged, I stepped up a hunt for a permanent private office that could be “Covid wave resilient” and even give GoCoach a footprint for collaborating in person, when the time arose.?

WeWork provided quotes for dedicated space that were slow to arrive and inflated by an imagined inventory constraint that clearly did not exist. They hadn’t learned their lesson, so I took my very limited budget elsewhere and settled in a nearly empty (and affordable) former WeWork facility on the East side that Regus had absorbed that spring as one of their Spaces coworking facilities. This was what I hoped to find and what the emergence from the Pandemic should look like for New York City - plunging commercial rents providing tailwinds for entrepreneurs and new businesses. Surrounded by an eclectic group of startups across tech, fashion and even cookware, I draw energy from the hustle around me, even if I only actually talk with my remote co-workers from my desk. I am just as productive as I have been for 20 years, when I was in an office, working with co-workers scattered around the country. While I do miss a good whiteboard session, I don’t miss fighting for a conference room to get on a call with colleagues in another office.

For nearly two years I had practically overdosed on “future of work” articles and podcasts, and now I was in it. After quietly and selfishly rooting against the foregone conclusion that the seismic shifts in how we live and work are permanent, I think I had finally arrived at a comfort with the permanence of remote work and saw a glimmer of the future for New York.

Around that time, I came across Cal Newport’s Interview with remote-work evangelist/entrepreneur Chris Herd in the New Yorker, Is Going to the Office a Broken Way of Working?, and it helped me untangle the cognitive dissonance I’d been experiencing: I could still personally hate working from home but embrace the value of remote work and remote-first organizations. I can draw my energy and focus from being out of the house, but that does not mean I have to be in an office with my colleagues. As an IRC user from the first dot com bubble until the rise of Slack, I had years of evidence that remote teams can work very effectively and happily. Along the way, my employers kept building slick new open-concept offices in city centers, to be competitive, only to shrink them year after year. Covid was just an accelerant to the trend that was underway.

What happens to all that space remains the existential question for Manhattan. But no city has resilience in its DNA like New York. This should be the spark that makes the city younger, hungrier and more innovative. Already the narrative that “everyone” abandoned New York has crumbled, as rents and home prices in the city soared back in 2021.

I’m over my hang ups and can say it loud and proud: Kristy and Rebecca got this right when they started GoCoach. The infrastructure to support remote work is opening up access to employment opportunities the way it has already expanded educational opportunities over the past two decades. If done right, being remote-first can serve as a competitive advantage for employers and a force for equity in the workplace, an idea that is central to the work GoCoach does with our clients.

And just months later, we have assembled an amazing team at GoCoach that spans the country from the Northeast corridor to Wisconsin, Oklahoma, Arizona and California. Freed of the constraints of space and geography, but united in our mission to provide deep, human-centered personalized learning, we can bring our full selves to work and provide great experiences for our coaches, learners and clients. And maybe this spring we will actually meet in person.

Just keep going

This past Thanksgiving weekend, Nathan took the stage at Lincoln Center for Opening Night of NYCB’s Nutcracker, a moment we weren’t sure would ever happen, an opportunity made possible only by the vaccines and by his persistence through months of Zoom classes that sapped him of his passion and almost led him to quit ballet.

I had wanted to see him back on stage in some capacity, as much as any of the changes I talked about making above, because it would mean that the public health situation had improved to allow some degree of normalcy, and it would mean that he had pushed through and put himself in a position to allow good things to happen again.?

Early in the pandemic, we watched JoJo Rabbit, and I’ve hardly stopped thinking about the quote that accompanies the closing credits:

Let everything happen to you

Beauty and terror

Just keep going

No feeling is final?

--Rainer Maria Rilke

Out of necessity, I’ve embraced the idea that uncertainty, even volatility, will continue to define the coming months and years. That is a tough lesson to swallow, more so for the Covid generation of school kids who risk developing a critical lack of faith in the rewards of planning and hard work. But I won’t stop working to help Nathan see that brighter days are ahead, and the choices we make now can make the days better.

So while I await warmer weather and declining Covid rates that should bring an even more energizing spring and summer than 2021’s aborted “Hot Vax Summer,” I’m heads down, focusing on the big and small ways I can contribute to building the future I want - for myself, my family, my city, and for GoCoach, where our focus is helping learners build the future they want.?

And I am heads up, appreciating as much as ever the opportunities and experiences coming our way.