On 5 Years of Writing Every Day

On January 1, 2020, I made a decision that would change my life: I started writing every day.

Prior to that, I didn’t write at all. In fact, I strongly disliked writing for most of my life. I was the “math kid” in school and the self-narrative I held was that math kids like me can’t write.

I started writing daily after reading Paul Graham’s “The Age of the Essay.” It shifted my perspective on writing and helped me see writing as a medium to clarify my thinking and explore ideas.

Everything I hoped writing would give me has been true—and then some. But often, the surprises bring the biggest breakthroughs. I’ve met one of my closest friends, landed my current job, moved to NYC, started a writing community, integrated myself into the NY’s creative scene, found my love for menswear. The list is long.

Yet, there were moments this past year when I came close to stopping this daily blog.

One of the reasons I started writing daily was inspired by the parable of the clay pots. For those unfamiliar, a professor split his ceramics class in two groups: one will be graded on quality, the other graded on quantity. At the end of the semester, the Quantity Group created the highest quality clay pots, not the group that was actually focused on quality. “Quantity creates quality,” as the saying goes.

Well, I’ve created 1825 proverbial pots at this point. I’m more confident as a writer than ever, and I felt it was time to shift from quantity to quality. I planned to retire the daily blog on its fifth anniversary—today. Five years and 1825 blog posts in a row is quite a run.

But as the day approached, I decided not to stop.

There’s a few auxiliary reasons for that.

First, a daily blog creates creative momentum. Over the years, I’ve met many people who started writing but eventually stopped. I’ve persisted because, even on the busiest days, I carved out just five minutes to write.

Second, a daily blog is flexible. It’s like a mental workout, much like going to the gym. Writing is thinking, and exploring ideas through writing helps in every aspect of life whether I’m focused on my my career, traveling a new country, or on mens fashion.

The main reason however, is as I began drafting the obituary for this blog, I reflected on my 1800+ posts. They’re a log of my life and what mattered to me at the time. Here are some highlights:

• 2020: The semester at the library and the start of the pandemic. I spent this time at home, recording my thoughts throughout.
• Early 2021: Wrestling with the idea of the corporate world versus being a creative. I decided to focus on my career, learning the recruiting game, and landing a great job—a decision that, in retrospect, was absolutely the right move.
• Summer 2021: Living away from home for the first time post-pandemic with friends in Montreal.
• Fall 2021: My final internship and the search for my first full-time job.
• Winter 2022: My last semester before graduating from uWaterloo.
• May and June 2022: My first solo trip to Colombia and Peru, living out my Anthony Bourdain fantasies, and falling in love with South America.
• July and August 2022: Moving to NYC, starting my first full-time job. Around this time, I also started a writing club with friends.
• Rest of 2022: Lots of observations around life in NYC and navigating post-grad life.
• Summer 2023: I started revamping my wardrobe and learning about fashion. I found out I really enjoyed learning about this.
• Late 2023 to Early 2024: Growing the Olive Tree Writing Club and exploring community building.
• May 2024: Heartbreak and realizing it wasn’t the right time to go all-in on OTWC.
• August 2024: Starting Riveting, a newsletter on menswear, and channeling my curiosity and energy into that project.

Reflecting on these moments felt like scrolling through a mental camera roll of my life over the past five years. I thought about how many stories and lessons would have been lost if I hadn’t written them down.

I also thought about what lies ahead: finding a life partner, transitioning to a creative career, starting a family, navigating life in my 30s, 40s, and beyond. These are potential blog posts that won’t be written if I stopped writing everyday.

Something about this blog feels sacred to me. It’s rare to find a project that holds your focus for a few months, let alone five years. I can see myself continuing this project for decades.

The dream is to one day look back at this blog when I’m 90 years old. To revisit who I was at 22 and share these reflections with my kids, grandkids, or anyone curious about the journey. Even if no one reads it, the act of being creative every day—whether for three hours or five minutes—is one that brings me so much joy.

That I can’t stop now.