What 100 articles taught me about thinking, friction, and the Shoggoth on the horizon
I can’t believe it. I have finally written my 100th design article. What was thought to be an impossible task when I first picked up the pen (or the keyboard) back in 2022 proved to be wrong. Today, I can finally claim a huge sense of achievement and relief. Not because I am done with writing — far from it — but because I continue to have much to say about design.
And as I write a new article every fortnightly, I come to understand myself a little better. The past me isn’t the same as the present me and most likely won’t be the same as the future me. How I think, how I feel, and how I act on those thoughts and emotions have changed too. Oscar Wilde says it best:
If you cannot write well, you cannot think well. And if you cannot think well, others will do your thinking for you.”
These days, the fear of not thinking well has not gone away. You might think that after writing 100 articles, I have the mettle of regurgitating new ideas into prose, that I have a magic box tucked away in my mind that could summon the most original thinking. I have none of those. Instead, I feel like one of the scared crews in Homer’s Odyssey, wondering what monster lurks on the island and when my hero’s journey ends.
In 2026, that boss-level monster on the horizon isn’t a mythical Cyclops. It’s something far more amorphous. I like to call it the Shoggoth: a sprawling entity with grotesque tentacles spilling out of its body while donning a placid, smiling mask. If this is new to you, the Shoggoth originates from the imagination of science-fiction writer H.P. Lovecraft. As writer Jürgen Gravestein puts it, they are shapeshifting creatures created as an instruction-following, slave-like workforce, always under their creators’ control. A bit like large language models. And if you squint really hard, you might actually see the logo of Claude.
I admit. As a designer and a writer, I have a love-hate relationship with AI. I love it for the pseudo-intellectual discourse I have with a sycophant agent. With its seductive charm and frictionless vibing, I could easily generate an article in an evening with a few prompts, saving me time to spend it with my family or doom scrolling on social media (with my wife).
And yet I hate it for how I have fallen prey to deceptive seamlessness without the same struggle of writing that my past self used to experience with the first few articles before ChatGPT. What made this ironic is that while technology is meant for good, the struggle is equally virtuous. Isn’t that what learning is about?
Some designers may view the struggle of writing as a waste of time, thus resorting to AI for quick fixes in their portfolio and work. I tend to agree that AI is a gamechanger for pointless emails. What I am more cautious about is whether we should outsource everything to AI. As Wildes framed it, do we want AI to do the thinking for us?
Anyone who reads and writes about design would know about Fabric Teixeira’s writing. As the co-founder of UX Collective, he advocates for designers to write because not only does our portfolio become multi-dimensional beyond pixels, but it also sharpens our craft and brings communities together. His view on AI is just as valid:
“The value of your actual voice, your real stories, your screw-ups, and your wins are even more valuable. The need for genuine human perspectives has never been higher.”
In many ways, this echoes the exact point of Michael Bierut’s legendary 100-Day Project. Bierut taught us that discipline is the ultimate vehicle for creative inspiration and that real growth only happens when we embrace the friction of repetition. My four-year timeline may have stretched his original design sprint of 100 days, but the core lesson remains identical: by refusing to outsource the labour of thinking, I forced myself to evolve.
What 100 articles taught me
My attention is now on how I will write my next 100 articles. In the world of AI, new designers may face a greater challenge of starting. Experienced writers also face similar challenges of sustaining. While there isn’t any silver bullet that will get you to the habit of writing, there can be ways of finding yourself in the process by learning from others.
Here are some lessons as I found my way into writing for myself:
Motivation
Somehow I knew I could share a point of view in my early days during design critique sessions. The problem was not taking the courage to write consistently, partly due to an imposter syndrome that lingered in my professional career. What became a breakthrough was after a spell as the head of design at Singapore Airlines, where I feared losing the intricate feelings I had in the best (and worst) times in an amazing organisation. This led me to write for myself with a goal of remembering. Over time, that same motivation grew into joy as I would revisit my older self through past articles. It was also uplifting to know that my words will become my legacy if my children ever read the rambling of their father. When the motivation is personal, its intrinsic value carries you forward.
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Space
I needed to experiment with what the optimal conditions were to bring out the best writings. For me, most of my writing happens at home in my kid’s room as they fall asleep. As a design manager in my day job, time is precious, leaving me with a 2–3 hour window every night to type with my smartphone. It also turns out to be the right moment for my flow state to kick in. When it came to tooling, I had tried various tools but eventually stuck with Google Keep for drafts, Canva for visuals and Mybib for reference compilations. I chose these tools for their simplicity to focus on my content. I would then submit my entries to UX Collective or Bootcamp before the editors publish within the next 1–2 days. This became a good rhythm of writing 2 articles every month and being pleasantly surprised whenever the articles get featured in the subsequent weekly newsletter. It gave me space and time to think and reflect on the next set of content.
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Voice
Turning voice into words can be tricky because every writer has a unique voice. I neither major in literature nor did well academically, which led me to adopt a ‘hacker’ or ‘heck-care’ mindset in putting words together. So I tend to be surprised when I occasionally see virality in some of my articles. One of my earliest hits was my rendition of the atomic design using Eame’s Power of Ten in 2022. LinkedIn and Medium lit with reactions and comments, and I glowed with pride. It didn’t last long, as my next articles went back to normality soon enough. My takeaway? Keep experimenting and finding your authentic voice. For the writer who continues to write will gradually find what resonates with them and their readers. I no longer fish for the next viral topic. Instead, I share what’s top of mind to me as a designer, offering an alternate analogous or contrarian view. That golden thread permeates topics around Figma, rethinking design or fighting a case against AI with human values.
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Authenticity
I wasn’t writing to make a living but to freely express myself. My articles were low-stake playgrounds where I would go on a wild ride. This was my channel to defy difficult stakeholders who preferred to stick to conventions. It was even my creative outlet where I didn’t need to align with my design leaders or direct reports. Sometimes, there can be nasty comments. A small number of them are valid, but more often, they are there because someone has something to say. What mattered was staying true to the perspective I was building. Over time, I realised that critique is just proof that something resonated enough to provoke a reaction. Writing authentically meant being okay with not pleasing everyone, so long as I didn’t dilute my own perspective.
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Forgiveness
There are definitely bad days where the mental block persists. Perhaps due to overwhelming work or an unsolvable problem, writing anything about design just didn’t happen. I dreaded those days because my sense of control slipped away. Other times were the loss of concentration or the nearly captured idea, only to reach a dead end. Trust me: there were drafts that never saw light because I lost the plot. Doing the maths will clearly show that there were dry seasons of no articles for weeks. I will admit that writing with AI came in. Not those that fix grammatical errors, but those that generate essays from a few prompts. So while I may think I could get away with slop, the funny thing about good publications is that they have seen enough AI slop entries to detect an article from the distance. My sins are exposed. My circumstances are unknown. It took forgiveness of my lack of actions and from my editors, who knew my work over the years, to move forward. Today, I still use AI for my work, but I no longer outsource my thinking to a soulless entity. I would put writing aside if nothing is coming out, and that’s okay.
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Joy
Let’s play a game. What if we could predict the next Pantone colour of the year? What will be the next Star Wars articles about design on May the Fourth (be with you)? Or how about the next article about circles on March 14 (3.14)? Joy is the most important lesson of being alive. Studying design in France taught me the seriousness of playful poetry. My design boss amplified the same point by acknowledging that a designer’s mood reflects the quality of the work. How true it is when you are having fun with concepts. Or a serendipitous conversation that became an entire essay. Creative writing doesn’t necessarily follow a formula. Instead, the idea ends up as writing, appreciated by people.
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Tribe
I had been very lucky these past 4 years. I still wonder how my first few articles were picked up by my editors. However, I stopped questioning and continued to trust the process. More importantly, writing has helped me connect with some of the most amazing designers. It has truly brought me to places unimaginable, both physically and cognitively. One such example was writing about Design 4.0, as the fourth industrial revolution in design connected me to Ilona Gurjanova, former president of the Estonian Association of Designers. Little did I know I was off to Estonia as a keynote speaker for the Tallinn Design Festival. Or how my work on modular journey maps ended up in Miroverse with more than 2000 views. Or the topic of design feeling transporting itself to platforms like DOC and the state of UX. Along with the countless mentions, reposts, comments and featured newsletters, I feel like I have found my design tribe beyond the island that I am living on. And that tribe is carrying me on to my next adventure.
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Homer wrote in Odyssey that each man delights in the work that suits him best. I’m glad to take the plunge of writing on topics that I am still in love with, even though the blank page is no less intimidating than it was in 2022. The Shoggoth of AI will continue to evolve, tempt, and disrupt how we create and think. But if these past four years have taught me anything, it’s that the virtue of writing isn’t in the output… It’s in the friction of the process.
We don’t write merely to produce words; we write to figure out who we are and what we believe in. So here’s to the next 100 articles, the next 100 struggles, and every quiet late-night insight along the way. I look forward to etching my thoughts in the present as memories for the future.
References
Bierut, M. (2025, July 16). The art of dailiness, by Michael Bierut. Itsnicethat.Com. https://www.itsnicethat.com/features/michael-bierut-the-art-of-dailiness-advice-education-creative-industry-160725
Gravestein, J. (2026). Shoggoth. Substack.Com. https://jurgengravestein.substack.com/p/shoggoth
Nolan, C. (Director). (2026). The Odyssey [Film]. Syncopy.
Teixeira, F. (2025, May 19). How to publish your design ideas on medium. The Medium Blog. Medium. https://medium.com/blog/how-to-publish-your-design-ideas-on-medium-1a8b6cf805bd
Rethinking writing in the world of design and AI was originally published in UX Collective on Medium, where people are continuing the conversation by highlighting and responding to this story.
