Only the (remotely) Lonely

On remote work and loneliness

Back in October 2016, I was laid off from an early-stage startup—along with half of the entire team. It was a heavy blow because I was excited about the product and I was learning a ton from my colleagues. Each weekday, I would hop in my car and make the hour-plus commute to San Francisco into the heart of the startup world. I loved the energy of the city and the startup scene. And then on that day in October, poof, all of a sudden I was at home looking for my next gig.

By early 2017, I was getting desperate. I had spent three months looking for a new full-time position. In the meantime, I had cobbled together a couple of freelance jobs. But they were temporary and didn’t pay well. I had to find something more permanent.

I was lucky enough to stumble on a job posting for a small startup that seemed like a great fit. It was a mix of remote work and office work (again, in San Francisco) allowing me to commute less often. I would be the first marketing hire on a small team. And I immediately hit it off with the CEO.

When I worked at the office, there were usually only four or five of us there and we were on a similar wavelength. We had interesting conversations, we shared the occasional laugh, and we collaborated on various initiatives. But when I worked from home, I felt isolated and disconnected from them. Chats on our company Slack would often devolve into unhelpful debates—sometimes lasting late into the night—where we would be talking past one another instead of working together to find solutions.

Now, this was my first foray with remote work for extended periods. At the time, I chalked up my disconnected feeling to just that—working remotely. I was at my house with my family, yet I felt alone. I started to dread what I would see each time I’d open my computer. This stress made it difficult to find the motivation to do the work and my productivity plummeted. After just six months, I started looking around for something new.

I quickly found a new position through a family connection and it led to this day:

For this new job, I mostly worked in our office in Sausalito. It was a slightly shorter commute and our waterfront office had incredible views of the harbor. Plus, I fit in great with the team and we worked well together.

I had the flexibility to work from home, although I rarely ever did.

And then, in March 2020, as Bo Burnham said in his song “All Eyes on Me”, the funniest thing happened.

When the pandemic hit, I was worried that working remotely would bring back those same feelings as before. The disconnectedness. The loneliness. Yet when I worked from home, it felt completely different. Our online chats were usually filled with funny banter instead of petty arguments. If there was some more delicate issue to discuss, we would hop on a quick phone call to iron out the details. But we would always be cordial with each other.

There was only one problem. I wasn’t inspired by the work.

Sure, it was a solid gig and it paid fairly well, especially when we had good monthly numbers. But I didn’t feel much passion or drive for the work beyond it being a vehicle for providing for my family and saving for our future.

For months, I spent my free time racking my brain trying to find my “thing”. It didn’t have to be a full-on career change. I felt the urge to do something creative, but I didn’t know where to focus that energy. So I started writing to work out my frustrations on the page. And then, with some encouragement from my wife, I realized that writing itself could be my creative thing.

One day, while in a couple’s therapy session, I described the urge I was experiencing and how I wanted to pursue writing. Our therapist encouraged me to follow my desire to write, as well, and she recommended I read the book Big Magic by Elizabeth Gilbert (author of the massive bestseller Eat, Pray, Love). The book is all about how to live a creative life and to push yourself past the fear of putting your work in front of other people. I devoured it over a few days, nodding along and getting more and more amped the whole way through.

The book also taught me what a memoir actually is. It’s a nonfiction book about a certain period of time in the author’s life, as opposed to an autobiography, which would typically be about the author’s entire life. Big Magic is a part-memoir, part-advice column, in a way. On the other hand, Eat, Pray, Love is most definitely a memoir. In fact, in many book publishers’ minds, it’s the quintessential memoir. In the past, when I thought of a memoir, I always pictured an old politician like Benjamin Franklin. He’s sitting behind a huge oak desk in his study, round reading glasses resting on the tip of his nose, smoking a pipe, and writing his life story with a quill or whatever.

Learning that Eat, Pray, Love was a memoir opened my eyes to the possibilities with my own writing.

I looked for other memoirs to read and came across A Heartbreaking Work of Staggering Genius by Dave Eggers. It’s about a period in his twenties when both of his parents passed away and he was forced to care for his younger brother. It’s tragic and emotional and hilarious. It ended up being one of my all-time favorite books and it inspired me to try to write in a similar raw, emotional, and sometimes funny style. I was off to the races and eventually launched this publication you’re reading right now.

I’ve previously written about how writing improved my mental health and helped me cope with the trauma around my daughter Em’s traumatic birth, among other benefits. Toward the end of the piece, I briefly mentioned this:

“Sharing my stories publicly and making new friends in writing communities has been helpful too.”

Reading it back now, it almost comes across as a throwaway comment. I didn’t mean for it to read that way at the time, but I now realize I sold this part short.

Sharing my stories publicly, connecting with my readers on an emotional level, and networking with other writers has not only been helpful, but it has also made me feel less lonely.

I’ve essentially been stuck at home since the pandemic started, for the most part. Having a kid under the vaccination age cut-off who also has a history of respiratory issues will do that. Yet I’ve felt more connected to other humans than I have in a long, long time.

I’m fortunate enough to not have to work full-time right now.

I’m on a quest to fulfill this goal:

And also not have to deal with these anymore:

In addition to online writing communities, I’ve been spending a lot of time in crypto-related rabbit holes and making new friends there. The vast majority of them I’ll probably never actually meet in person. And I have no idea what some of them even look like. But I still feel connected to them and I feel less alone, even though I’m mostly staring at a computer by myself throughout the day.

Nowadays, when I open my computer in the morning, instead of dreading what I’ll see, I’m excited to discover what’s waiting for me.

Huge thanks to Mark Koslow and Cole Feldman from Wayfinder for helping me steer this piece in the right direction.


And thank you for being here. If you have been enjoying my writing, it would mean a lot if you shared it with one friend today. No pressure.

At the very least, if you enjoyed this piece, could you please let me know and tap the heart button below?

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