Choose Life

A young George Michael wearing Katherine Hamnett’s “Choose Life” shirtA young George Michael wearing Katherine Hamnett’s “Choose Life” shirt

Katherine Hamnett is an English designer who was one of the first to popularize graphic tees with big bold messages. Her most famous example is an oversized white tee with black block lettering that read, Choose Life. George Michael famously wore this shirt in the music video for Wham!’s Wake Me Up Before You Go-Go.

Inspired by a Buddhist exhibit, Hamnett created the Choose Life” shirt as a commentary against war, deaths, and destruction.

July 23, 2024

Gen Z needs to stop having situationships with everything

It seems like many of my friends are in situationships with everything. I’m not just talking about relationships. I’m talking about friendships, jobs, cities, communities, hobbies, everything.

Part of it is because there’s always hope that there’s something better out there. Yet, in my own experience, optionality is overrated.

My fulfillment comes from my willingness to commit. I find this is becoming increasingly rare and is an easy way to distinguish yourself in NYC, the city with the ultimate optionality.

I’m willing to commit to my relationships.

I’m willing to commit to writing every day for almost 5 years.

I’m willing to commit to organizing a weekly writing community for 2 years.

I’m willing to commit to living in NYC long term.

There is no right decision, the right decision is the one you commit to.

July 22, 2024

Advice from an Old Head

I came across this advice on Instagram that I thought I’d share:

Credits to @kareemCredits to @kareem

Here are a few thoughts:

  1. Ambition is contagious. I always feel energized after talking with my ambitious friends.

  2. I’m going to add this post it note to my wall too. I tend to overthink things which prevents me from doing the work.

  3. This is a theme for me this year.

  4. How does one build this pain tolerance? This is a blog post for another day. Fundamentally, your motivation has to come from a pure and honest place.

  5. Serendipity doesn’t happen in isolation. This is the case for job opportunities, projects, and meeting someone special.

  6. Finding mentors is overrated. Finding peers and mentees is underrated.

Aside: I thought this Insta post came was from the basketball GOAT and one of my role models, Kareem Abdul Jabbar, because he’s the Kareem I know on a first name basis. It wasn’t until I linked the post after editing this piece that I realized it was not KAJ.

July 21, 2024

Everything You Need to Know About Caring for Your Clothes

In Japanese culture, there is a belief that all objects, animate or inanimate, possess a spirit. This reverence extends even to the most ordinary items.

Similarly, I view my clothes not merely as transactional garments, but as objects with a spirit that deserve care and nurturing. In the age of fast fashion, we often treat our clothes as disposable. Instead of properly maintaining them and repairing them when necessary, we discard them and buy new ones. This is a wasteful approach. I encourage people to adopt a more mindful approach to their clothing. Buy less, but invest in higher-quality pieces.

Take care of your clothes and they’ll take care of you. Over time your clothes will age gracefully, fostering a deeper attachment. By nurturing our clothing, we can honor the spirit within each garment.

Here are a few tips for taking care of your clothes:

Washing

Storing

Maintaining

July 20, 2024

The Taste and Skill Gap in Fashion

An idea that I’ve wrote about a few times is the gap between taste and skill. As a creative, this gap always exists; it’s part of what motivates us to get better but also frustrating because taste and skill are asymptotic. Your skill will never be as good as your taste.

Fashion taste can evolve quickly these days. We’re constantly exposed to fashion through social media and other daily influences. What’s frustrating about fashion os that your styling skills are only as good as your wardrobe. Without the right pieces, you won’t be able to fully execute the looks you envision.

Fashion enthusiasts are driven by a constant desire for new clothes. As their tastes evolve, they may seek to improve their styling, but the underlying motivation is the pursuit of acquiring novel garments.

July 19, 2024

10 Things I Learned About My Personal Style This Year

In a previous blog post, I wrote that building a wardrobe takes 5-7 years. This is because it takes time to develop a personal style, and then to find pieces that match that style.

Developing a personal style is a process of trial and error. I may think I know my style, but then realize I don’t like certain pieces I’ve bought. Or I’ll try on something that isn’t my typical style, but I end up liking how it looks on me.

This year, I’ve learned a lot about my personal style. Here are 10 learnings:

  1. Three words I’d use to describe my style are subtle, elevated, and contrasting.
  2. I’ve worn slim-fit pants for years, but after trying different styles, I’ve found that regular-fit pants with a high waist are my favorite.
  3. I prefer relaxed-fit button-ups, oversized sweaters, and slim-fit t-shirts for tops.
  4. Collared shirts > T-shirts.
  5. I don’t need to stick to my size”. I would always buy tops in a mens small but since sizing isn’t standardized in the industry some pieces look better on me in a size medium or large.
  6. Boots, Loafers, Derbies > Sneakers.
  7. Indigo is my favorite color.
  8. Much of my style inspiration comes from Japanese fashion. Many of my favorite brands are based in Japan like Kapital, Momotaro, and BEAMS.
  9. My style most closely aligns with Drew Joiner. He’s also my favourite fashion creator right now.
  10. The story of a brand and a piece is just as important to me as the aesthetics.
July 18, 2024

Living a Rich Life Outside of Work

My friend who recently visited New York City remarked that everyone seems to have a side hustle. We all have our regular jobs, but we also write, paint, or DJ in our free time.

I was talking with my friend, J, and after knowing her for nearly a year she asks me, So James, what do you for a living?”

I have a few close friends whose jobs I’m unaware of.

I don’t actively avoid discussing work with my friends. We live rich lives outside of work and the topic of work just doesn’t come up.

July 17, 2024

Make Space to Miss It

Two months ago, I was going through a tough breakup and I had an OTWC event that I was hosting on the upcoming Sunday. Despite my personal struggles, I wanted to put on a good show for the community members who had already signed up to attend.

And I’m glad I did, that event was a reminder of why I host the OTWC. During this session, I wrote one of my favorite pieces of the year - a short personal piece describing the emotions I was feeling at the time. I was also surrounded by the love and empathy of the community, something I was grateful for at the time.

Organizing the OTWC isn’t easy. I often doubt if I’m built” for this. Yes, it’s stressful, it’s time-consuming, and I’m often anxious about our next event. Yet, I find so much joy in organizing the events, serving the community, and meeting other writers. The joy far outweighs the pain.

We’ve been on pause for the past few weeks and it’s during our breaks that I’m reminded how much this community means to me. I wouldn’t trade it for anything.

July 16, 2024

OTWC is Back to Weekly

This is a cross post from OTWCs Substack

For nearly two years, we hosted weekly writing events in the city.

Earlier this year, we made some big changes, one of them being the transition from weekly to monthly events.

During that time, one thing became clear: the weekly cadence is an essential ingredient that makes OTWC special.

Sometimes, giving space allows you to appreciate what you miss.

It’s time to bring back what works.

Starting on Sunday July 28th, OTWC is back to hosting our weekly writing sessions.

Join us every Sunday morning throughout the rest of the Summer.

RSVP for our Season 3 Kickoff here.

Hope to see you there!

July 15, 2024

How I Got into Fashion

Back in elementary school, the popular trend was big, bulky, and colorful G-shock watches. For my birthday, my parents got me one. It was a black G-shock that was bigger than my pre-teen wrist with red accents loaded with features I didn’t need like the moon phase and tide graph. I loved it.

I broke necks the first day I wore it at school. One of the popular kids asked if he can borrow it for a period. My status instantly elevated to that of one of the cool” kids. As a status-conscious, insecure, teenage boy, this is when I started associating dress with status. I wore that watch daily for the rest of the school year. And this mindset continued throughout high school and early university.

My university had strong engineering and computer science programs so naturally I gravitated towards a career in technology. One unique characteristic of the tech industry was the lack of a formal dress code. Many of the most prominent figures in tech famously flexed their minimalist wardrobes. Steve Jobs with his signature Issey Miyake black turtleneck, medium wash Levi’s 501 jeans, and gray New Balance 992. Or Mark Zuckerberg with his daily uniform of a tee and jeans which he says reduces his cognitive load in the morning. Tech was seen as anti-elite. You couldn’t judge someone by how they dressed because they could be building the next big unicorn.

Embracing the tech uniform gave me permission to not care about what I was wearing. I thought it was refreshing. I thought this was how it should be. No one else around me cared either. I traded much of my wardrobe for plain basics - white sneakers, t-shirts, and pants.

I started to dress and look like everyone else.


My style remained largely unchanged in my late teens and early twenties.

Then in early 2020, I had a conversation with a friend that became the catalyst for my fashion journey. I was back in my hometown and I bumped into an old high school friend at the gym. We haven’t talked since senior year of high school and the first thing he says to me is, James, you look exactly the same.”

The last time we talked, I was 16, I was still a kid. I was 22 now. Internally, I grew so much. Externally, I looked the same. My friend likely assumed that because I looked the same, I was the same.

My friend’s comment made me realize there was a disconnect between my self-perception and how I expressed myself through how I dressed. Ever since that day, I became hyperaware of this gap.


In the Summer of 2022, I was celebrating my one-year anniversary in NYC. I’ve been working full-time now for a year now so I had some disposable income. It was then that I decided that the timing was perfect.

During that Summer, I became a student of fashion. I donated 90% of my wardrobe and built it up from scratch. I bought textbooks, courses, and discussed this with my friends in the industry. Living in New York City, one of the world’s fashion hubs, I was constantly inspired by the outfits I observed on the subway, in coffee shops, and while walking throughout the city. I viewed every clothing store as a classroom and engaged the sales associates as if they were professors, asking them questions to expand my fashion knowledge. Every day I was learning something new.

Fashion is a cultural language that I was becoming fluent in. It’s an art that everyone participates in every day. What you wear reflects who you are and the best part is you can choose to be whoever or whatever you want. You can use your clothing as a canvas to express yourself — show different styles, tell a story, or represent your personality.

My style is my story. It’s a reflection of who I was, who I am, and who I want to be. In the past, I was an engineering student, a musician, a breakdancer, a Torontonian. Currently, I’m a Technologist, a Writer, a Filipino-Canadian, a New Yorker. To craft a stylish wardrobe means to infuse my story into the different pieces, I want to honor my roots, and dress like the person I want to become.

July 14, 2024

Make Your Writing Sing

I’m often asked what makes great writing.

One overlooked aspect is rhythm. It’s making your words sing in a way that engages the reader.

The above example from Gary Provost illustrates this beautifully.

July 13, 2024

You Don’t Need to Read

In a 2015 interview, Kendrick Lamar was asked if he reads a lot. Here’s his response:

Naw-uh… I’d rather be interacting with a person than gathering up information from somewhere else. [I’d rather] speak to a person with wisdom that’s been here before me.

Kendrick Lamar was the first hip hop artist to win a Pulitzer. Given his complex lyrics and the subject matters he raps about, I assumed Kendrick was an avid reader. It turns out that’s not the case.

If you live an interesting life and surround yourself with interesting people, you don’t need to read. Personal experience is enough.

July 12, 2024

Blue Collar and White Collar

Blue chambray shirtBlue chambray shirt

The term blue collar refers to manual laborers while white collar refers to knowledge workers. But where do these terms come from?

Blue collar refers to the blue-colored denim or chambray shirts commonly worn by factory, construction, and other types of manual labors. These shirts were durable, easy to maintain, and the blue collar concealed dirt and grime.

White collar comes from the white dress shirts worn by professionals who work in an office environment.

July 11, 2024

Just Spend 5 Minutes

Want to write more? Spend 5 minutes tomorrow writing on your notes app.

Want to read more? Instead of looking at your phone while waiting in line, crack open a book and read for 5 minutes.

Whatever habit you want to build. Whatever skill you want to learn.

Just spend 5 minutes.

It all adds up.

July 10, 2024

Fall Down Seven Times, Get Up Eight

Failing is a natural part of any dream worth pursuing. Part of the fulfillment and joy of the journey is pushing yourself beyond what you are capable of. But that also means you’ll fail. And you’ll fail a lot.

Nana korobi, ya oki is a Japanese proverb that translates to fall 7 times, get up 8. It embodies the spirit of perseverance, persistence, and resilience necessary for any journey.

I fell a few times this year. One I’m still getting back up from. But from these failures I learned where I need to grow, I learned humility, and I learned more about myself.

July 9, 2024

What to do when the party is dead”?

My friend, Ethan, told me a story worth sharing:

During my last night in Rio de Janeiro, I planned on meeting up with some hostel friends at a nightclub. I arrived past midnight, and they were already there. They were complaining about the vibes and atmosphere at the club. My friend told me that it was dead in here.”

Feeling inspired in the moment I gave a pep talk; If the party is dead, you have two choices: complain about it or turn it up.”

Prior to entering the club, I was present, I was grateful, and I was ready for an amazing evening. The fact that the club was dead” did not stop me. I went on the dance floor, I felt the music, and I moved how I felt like. I didn’t consume alcohol to get drunk, but to feel energy and excitement. I was living in the moment. I was in a state of euphoria and I wanted to share my energy with those around me. Eventually, my friends joined me, strangers joined in, and we all danced together. The club came to life. It felt like a dream.

I had one of the best nights of my life, we all did. To become the life of the party wasn’t my aim. My only aim was to be present, engaged, and share my energy with those around me. Becoming the life of the party was just a side effect.
July 8, 2024

On Repeating Outfits

From the Lizzie McGuire movieFrom the Lizzie McGuire movie

If I’m going to a function, and I know that at least one person has seen my fit before, the above dialogue plays in my head. In the fashion world, an outfit repeater is almost seen as a criminal offense. Then I realize I don’t give a fuck. No one else cares too if you’re wearing the same outfit twice.

Outfit repeater” is a result of the social media age and fast fashion. You don’t want to be seen on social media wearing the same outfit and fast fashion has made it easier than ever to have the trendiest, newest piece, for next to nothing.

The irony is that some of the most stylish people wear the same outfit daily. To have a daily uniform is the apex of having a signature style. It shows self awareness and confidence in their own style. Rick Owens, Bill Cunningham, and Karl Lagerfeld more or less have worn the same outfit for years, yet no one calls them an outfit repeater.

I too have little desire to have a large wardrobe. I prefer a smaller wardrobe with high-quality pieces that I wear for years. This means that I do repeat outfits and I’m proud to do so.

July 7, 2024

Menswear is Functional, Womenswear is Form

Many menswear garments today are historically rooted in function. For example, denim jeans were made for the gold miners in San Francisco. Or chore jackets featured many pockets for French labourers.

Traditional womenswear, on the other hand, seemed to focus on form. Think of dresses, high heels, and skirts.

This is another example of how clothing is a mirror of the cultural zeitgeist and how gendered clothing reinforces stereotypes.

July 6, 2024

Less Goals, More Experiments

Whether it be writing, recruiting for a job, or getting ripped, I’ve proved to myself that I can repeatedly set goals and accomplish them. Each time I achieve a challenging goal, it boosts my confidence and reinforces my belief that I can accomplish any goal I set for myself.

This year, my focus has been on my creative goals, but I’ve tended to overthink and lack execution. What’s difficult about setting goals for my creative life is that there’s a multitude of paths I can take. There’s no right answer. Instead of focusing on goals, I’m shifting my mindset to an experimental approach. This means less overthinking, less goal-setting, and more trying out different ideas to see what works best.

July 5, 2024

On Having a Niche

One of the biggest conflicts in my creative life has been whether to niche down or not. Every playbook on how to grow an audience says that you need to focus on a niche to grow. My beef with this idea is that having a niche feels unnatural. We’re complex, multifaceted beings with a variety of interests. Why limit yourself to a niche?

I’ve seen it happen time and time again. A creator niching down and feeling stuck because they pigeonholed themselves. They become a victim of their own success.

But now I understand that I needed a mental reframing. I wrote a post the other day on newness vs nuance that has been living in my head rent-free. Beginners find novelty in newness, while masters find novelty in nuance. Writers like Matt Levine, Ryan Holiday, and Arnold Schwarzenegger have daily newsletters they’ve been writing for years about one topic. Matt Levine writes about finance, Ryan Holiday about stoicism, and Arnold Schwarzenegger about health and fitness. Especially if you’re genuinely curious about the topic, you can go infinitely deep into it and not run out of ideas to discuss. That’s how you focus on a niche in an authentic way.

July 4, 2024

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