Writing and me

I’ve now managed to somehow keep this blog going for well over five years, and I often get asked how I’m able to consistently write blog posts on a schedule. My relationship to writing has evolved over the years, and I’ve somehow landed on a system that works well for me. Figured I might as well write about it.

Throughout childhood, I was an avid reader. My favorite genres were dystopian sci-fi and high fantasy. My only experience with writing was whatever assignments and essays I had to do for school. I actually enjoyed a fair bit of the creative writing I had to do in high school, I just wasn’t a fan of the environment I had to work in and the general everyday stress of being a late teenager who’s supposed to have everything figured out and set sail towards their ideal life path.

In college, I studied engineering and was exposed to a different style of writing — technical writing. When writing scientific papers and explaining deeply technical concepts, we were taught to be as straightforward and concise as possible, using as little flourish and fluff in the sentence structure as we possibly could. I would always try to add some similes or metaphors, little jokes here and there, only for all of them to get edited out by my professors. This annoyed me a little because it left no room for creative expression in the writing, but I understood why it was the way it was.

After college, I had started working at a job I absolutely despised. It was technical, boring, dry, and felt like a lot of engineering grunt work. I desperately needed a creative outlet. I tried drawing, digital art, kickboxing, running, traveling, playing music, and just a wide variety of things to channel all this creative energy into. Writing, surprisingly, was one of the activities that I was able to do the most consistently.

I was in the beginning stages of starting a career transition into working as a full-time designer, and I had started an online blog (now deprecated) to document my learning process for design. It also doubled as a way to stay relevant in the industry by showcasing to peers that I maintained a design blog. I wrote a lot of case studies, teardowns of why certain apps were poorly designed, design trends, UX learnings, and the like. It was very specific in its content, kind of like the technical writing I was taught in college. It also took a long time to plan out and write these posts.

I then stumbled upon this technique from Srini Rao about how writing a thousand words a day changed his life (I had heard it on his podcast The Unmistakable Creative first, which he then translated into a blog post a few years later). He wasn’t publishing these in a blog. He simply wrote for the sake of writing. This was a markedly different approach from what I was doing. I was writing for an audience and was carefully curating the post to flow in the typical structure of an introduction, some explanations, lots of visual imagery, and a conclusion. What Srini was proposing was a different type of writing, one that’s freeform and more open-ended in its format. No one else was to read it. It was purely writing for yourself. And there were no rules. So I gave it a shot.

This was in November 2014 (six years ago now), and I recently stumbled upon them again. I was struck by how different these were to my earlier technical-esque writing. These were random posts about anything — design, life, culture, travel, games, space, relationships, and humans. And they allowed me to express my thoughts in a really unique way. I may not have realized it at the time, but this was a powerful creative outlet for me. I didn’t know how many thoughts and musings about the world I kept bottled up in my mind until I let them spill out on paper.

Upon re-reading my earlier 1000 words a day posts, I noticed that my writing style was a lot looser. Sentences flowed into each other with lots of variation and style, I used a lot more similes and metaphors, and I had a unique half-witted sense of dark humor when it came to my general outlook on the world. I was amazed by how much these posts subtly hinted at my overall negative worldview through nuanced expressions and adjectives hidden in the writing. Something here was definitely working, and it served so well for me to just pour out my thoughts into an Evernote doc for no-one else to see but myself.

This lasted for about 45 days until I couldn’t figure out what else to write about. I wrote a thousand words a day every day for 45 days in a row. This was impressive to me. 45,000 words felt effortless. But I wanted to see how much longer I could keep it going, so I started writing fiction. I penned down a thousand word prologue for a random space exploration story I had and then kept it going for some ten chapters, each containing a thousand words. I recently re-read it and was left impressed by my own ability to come up with such vivid analogies and prose structure.

I introduced characters in unique ways. I “showed, didn’t tell,” I put characters in interesting situations that made the reader care about them, and I had nail-biting cliffhangers at the end of every other chapter. I even alternated character perspectives for each chapter — a storytelling technique undoubtedly influenced by A Song of Ice and Fire, which I was reading at the time. I abandoned this pursuit of writing fiction ten chapters in because in real life, I had to move cities, start a new job, and adjust to a very different lifestyle. So I sort of stopped doing this thousand words a day pursuit, but I’m grateful for how much self-confidence it gave me in my own writing abilities. I actually felt like I knew how to write in a way that was clear and articulate in its message while occasionally being able to infuse humor and rhythm into it when needed.

After a few months of being a full-time designer, I started this blog that you’re reading now. My initial goal was to keep each post short and simple. My biggest downfall with my earlier design blog was that it took too long to plan out and write a post, create and compile all the images, and explain everything in detail. So I wanted to cut down on the time it took to write a post by scrapping the images and maybe only writing a few paragraphs per post. This worked in the start and I decided to loosen the constraint once I learned that I had a lot to say about specific topics.

My goal of writing six blog posts a month quickly fluttered out of existence once I ran out of topics to write about in a few months. I decided to then only write posts whenever an idea came to mind or whenever I felt like I had something to say. The idea was to not pressure myself to write when I didn’t feel like it, because this just leads to a lot of stress and pent-up anxiety. For about a year or so, it went on like this, with me writing whenever I felt like it. There were some months when I wrote six posts, some months where I wrote two, and some where I wrote none.

In 2017, I decided to try out a new method that I accidentally stumbled upon. I noticed that I had a somewhat consistent pattern of writing around three blog posts every other month or so. So I established a rule where I would follow this pattern, writing three posts every other month. And this worked brilliantly. I managed to write eighteen blog posts in 2018, 2019, and am on track to do it in 2020. This ended up being the perfect balance on when ideas came to me and when I felt like writing about it. It never put me in the position of “what do I write about now?” or “oh no, I need to figure out what to write about,” which was a welcome change.

The content of the posts vary from design to life to travel to games that I’m playing at the time. Again, very diverse and in-the-moment without any pre-planning. For writing the posts themselves, I just sit down and let the words pour out, similar to how I did my 1000 words a day posts. Except this time, it was public and there was an audience. Although not really, because I don’t really advertise this blog anywhere. It’s accessible from my main site for those who are curious, but I’m not exactly undertaking the digital equivalent to plastering flyers all over the city.

I’ve also written very long case studies of my design process on Medium. In lieu of keeping a traditional design portfolio, my Medium profile serves as a dump of case studies where I explain my design process in-depth, something that a series of fancily angled screenshots could never compete against. I also write in detail about video game UI design, a field I’m passionate about and partake in as a freelance designer. Aside from helping my career growth as a designer, writing about design has really catapulted my abilities to talk intelligently about design into the highest leagues of design writing publications. I’ve found writing to be a very valuable asset to any designer, and would encourage all designers to do it.

Outside of this blog and my Medium posts, I write extremely long letters to my future self at the end of every year (through FutureMe), one year into the future. I document in detail everything that happened in the year and what my goals for the next year are. It’s always fascinating reading where I was a year ago, how I expected things to go in the next year, and then thinking about what actually happened in that year (which I then wrote about in another letter one year into the future). It usually ends with some profound note of how to temper my own expectations of my life and what’s to come. These letters take multiple days to write, and I’m hoping that one day, these will serve as a useful portal to my younger self as I read them in the far future. These end up being extremely personal and are, like my earlier 1000 words a day prompts, for my eyes only.

So yeah, my relationship to writing has evolved in a fascinating way over the years. From some light creative writing in high school to technical writing in college to it literally being a creative outlet after college and having evolved into multiple blogs, hour-long Medium case studies, and novel-length letters to my future self, it’s definitely something I cherish and appreciate the more I do it. I find it much easier to communicate in the written word rather than an in-person dialogue. Often, when someone asks my opinion in a meeting at work, I’ll say I’ll circle back about it and get back to them, because I find it easier to explain my thoughts in writing in an email or Slack message rather than saying it out loud on the spot. It’s just what works best for me because it allows me to explain my thoughts as best as possible.

So yeah, maybe I’ll pick up writing that novel back again now that I’ve re-assessed my relationship to the written word. A part of me feels like my writing skills are deteriorating the older I get. The best way to keep them sharp is to just write, write and write more. It really has reshaped how I think about myself, because it’s just me putting my thoughts down and converting it into a comprehensible series of sentences. I’d highly recommend picking up writing to anyone who wants to better understand themselves. Start with the 1000 words a day prompts and just write for the sake of writing. Who knows what wonderful places it’ll take you?