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I can’t identify the exact moment I decided to sit down and start writing. My first essay was about chatting with people at the register or behind the counter at stores. The quick conversations I was having was affecting me and I could see it was affecting them. Coming to London, I had put myself into a position of having very few friends and people to talk to throughout the day. I had left a city where I had numerous friends and a job where I worked with like minded people to come to a place where I knew only a handful. At school, I tried to stay focused on the material and was stand offish with many of my classmates. The short interactions with cashiers, while not entirely new in my life, were taking on new meaning and importance. Combined with the time I now had for introspection, I was exposed to the value of these conversations. If I didn’t see it before, surely my friends and family weren’t seeing it either.

That’s how I like to think back on my foray into writing, though the real story is probably less humble. I have always seen myself as well tuned to the world around me, seeing the undercurrent of motivation that propels people toward different actions. The best writers are able to convey those same driving forces through characters and stories with such ease. Before they build a narrative, they research and discover. They spend time with the subject and learn what is actually happening. Writing is only as good as it’s ability to connect with the reader, and if a writer can put themselves in the shoes of the subject, it makes the storytelling a process of recounting rather than fabricating.

When a friend questioned my ability to become a successful writer, for writers had to start much earlier than my 28 years of age, I definitely took offense to it. Sure, I hadn’t been a very good writer in school, and at that point hadn’t written anything serious for years, but communicating through elegant prose never felt essential. I had been moved by books from Malcom Gladwell and Michael Lewis, authors who didn’t just write well but were astute observers, and believed I could do the same.

When making the move to London, there was a side of me that wanted to explore the artistic potential I felt I possessed. Combined with my newly acquired time and patience, along with a sprinkle of the get-er-done attitude I’d obtained in the startup world, I got to work on creating my blog and the newsletter to go along with it. It’s inspiring to be in a time where it’s so easy to get in touch. That said, the more I’ve written and the more weekly newsletters I send, the clearer it becomes that technology is only a means. The real effort and value comes from the time set out to think through and write an article. I’ve spent countless hours at the keys of my computer, writing down thoughts for essays. Often times, there’s no writing at all and I sip my coffee in silence, thinking through a possible story. It’s a laborious process, occurring so often within the head before there’s anything to show. And this work doesn’t stay within writing sessions. Riding the subway, talking to people, or watching TV all become possible leads for a new story. It becomes nearly impossible to avoid jotting down a spark of an idea when it hits. There’s so much joy in the process but simultaneously it can be exhausting.

“Great writer” is not a title I would attribute to myself. Having moved to San Francisco years ago with the goal of eventually starting a company, it’s titles and quantifiable statistics that I constantly have looked at for verification that I’m on the right track. With the blog, it would have been easy to take a similar path. Not only does MailChimp make it easy to send my newsletter, but it’s just as easy to track the number of people reading and opening. When I started the Weekend Unwind, I immediately added my family and closest friends. That decision changed my entire outlook. Rather than a chance to build an audience and see how big it could get, my blog has been a way to communicate with the people I’m rarely around but with whom I want to be discussing life. If I wasn’t able to add a single person to my subscriber list, I had the attention of the most important people and what could be better.

Writing has become one of the most enjoyable parts of my life thanks to the people who read my work. There’s short email replies, follow up conversations, and compliments from those who I haven’t talked to in years, some who I’ve never met. Having been so focused on my career for so long, and putting such a large amount of time and energy into that endeavor, the result of writing makes me question what I’m truly optimizing for.

I mentioned a few essays ago how strongly human connection is correlated to happiness, a sentiment I’ve experienced first hand. From the outside, before I began writing, there was a feeling that the writer is conversing with himself. It became very clear, very rapidly, how wrong I was.

It’s a lot of work maintaining this blog and newsletter. I feel a bit of pressure to constantly write. I have a small audience now, and that’s something I don’t want to spoil, if only for the pressure it provides. But the real pressure comes from myself. I see the world with a depth and curiosity I never would have expected. More than that, I’ve revived relationships I thought had been gone and improved many that I thought had peaked. It may have started as a challenge to be a great writer, but I’m not sure that even matters anymore.


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