In early COVID, Ken Sakata was in his mid-30s, working as a surgeon in Australia. Then he started making real merch for a fake Australian football club and posting TikToks about it. He continued to pull that thread and reactivate a lifelong but dormant passion for design. Sports hoodies led to a “Front Office” collection, designed for the fictional club’s management staff: essentially an excuse to start designing clothing for real.
I wrote about Ken back in mid-2024. By then he’d started to take the brand more seriously and was growing as a creator of short video essays about interpreting designs and the ideas behind them. I was excited to see someone iterating toward their thing and enjoying one of the internet’s great superpowers: niche-at-scale.
Today, Ken lives in Tokyo and is a full-time designer. He moved there early in 2026 to take his brand, Front Office, to the next level. The business has nearly died several times and he’s not out of the woods yet. But he’s going for it.
He’s shed the fun and games and is deeply serious in his attempt to design meaningful things. He writes here on Substack still creates some of my favorite videos on Instagram (yes, the bar is low as far as IG reels go, but trust me), and he wonders in our conversation whether his destiny is to be something closer to the Anthony Bourdain of fashion than to follow in the footsteps of the great designers he admires. But he’s committed to attempting to be great anyway.
If you’re interested in craft, commerciality and creativity, and chasing dreams, I think you’ll enjoy the conversation and Ken’s work. You can subscribe to him here:
Please enjoy! Available on Spotify, Apple, YouTube, other podcast platforms, and here on Substack. Full transcript and links here.
Dialectic 63: Ken Sakata - I Want To Find Out
Description
Ken Sakata (Instagram, Substack) is the founder and designer of his fashion brand, Front Office.
Ken was a surgeon in Australia until a fake football club he invented during COVID turned into merch and woke up a lifelong dream to be a designer. His short video essays on the history and craft behind everyday clothing made him one of the internet’s best explainers of fashion, and this year he moved to Tokyo to take his work to the next level. I wrote about Ken in 2024 and have been following his journey since.
We talk about leaving medicine, whether creative work is selfish, and clothing’s mix of utility, status, and art. We discuss getting good quickly, what makes a garment meaningful, why fashion keeps looking backward, and Ken’s worry that he may be destined to be the Anthony Bourdain of fashion rather than a great designer.
I hope you are inspired to pull loose threads, take dormant dreams seriously, and find out what you’re capable of.
Dialectic is presented by Notion. Notion is a collaborative workspace for your life’s work and the place that holds your context as you work with AI. Notion’s new auto model router picks the right model for each task, Notion agents can now use a browser and a computer and work for up to 24 hours, and Notion’s MCP lets the AI tools you already use work from the same context. Learn more at notion.com/dialectic.
This episode is supported by Google. Genie 4 is Google DeepMind’s latest interactive world model: a live simulation that responds to where you move and look, your prompts, and your voice. Genie 4 is in research preview. Learn more: https://deepmind.google/blog/genie-4-a-new-generation-of-world-simulation/
Timestamps
(0:00) Intro: Ken Sakata
(3:54) Start: Optimism and the Impractical Dream
(8:04) Leaving Medicine and Whether Creative Work Is Selfish
(17:16) Design as Problem-Solving: Utility, Status, and Art
(32:36) Finding Your Weapon as a Designer
(39:43) Mistakes, an Unlikely Path, and Iterating
(51:25) Designing Meaningful Things and Cultivating a Point of View
(1:00:03) Focus and Pulling the Thread
(1:14:18) Front Office, Jil Sander, and Clothes for Walking Around a Museum
(1:25:18) Why Fashion Keeps Looking Backward
(1:37:20) What It Would Mean to Be Great, Busking on Instagram, and Bob Ross
(1:45:37) The Anthony Bourdain of Fashion
(2:01:20) Japan, Craft, and Curation
(2:16:08) Books, Editing, and Generous Mentors
(2:24:49) Advice on Clothes & Closing Questions
