Reflections from Olive Tree Writing Club Season 5 Kickoff
I’m so grateful for this community. Through it, I’ve met some of my closest friends, people who continue to inspire me every day. This group is part of what made New York feel like home, giving me not only a sense of belonging but also a sense of purpose.
One of the reasons I moved to New York in the first place was to find a writing community like this. Little did I know that I’d start one myself. I had no plans of becoming a community organizer—just a desire to solve my own problem.
Yesterday’s kickoff was a beautiful mix of old and new faces—some friends who’ve been with us since 2022, others who joined last year, and new folks just finding their place. That’s what I love about this group: it’s always evolving, yet it feels so grounded.
I’ve written about this before, but I’m drawn to the kind of people who enjoy writing. This group not only lets me see my writing friends every week but also makes it easy to meet new ones. I can’t imagine what my life would look like without it.
Recently, a friend told me, “You’re building a writing community in one of the greatest writing cities in the world. That’s impressive—and you’ve kept it going for two and a half years.” He’s right. It’s not easy to commit to something and see it through especially in NYC. There were a few times when I thought we were going to shut it down. But I’m so glad we didn’t.
Tackle Your Fear Incrementally
If you’re scared to do something, take it step by step.
For example, I meet many people who are scared to write online.
Instead, start small—create a private Substack with no one on it. Post there to get comfortable with the habit of sharing. Once that feels manageable, start sharing your Substack with close friends. Maybe commit to posting weekly. Then you can make your Substack public but you don’t have to announce it to everyone yet. Once you get comfortable there, then share one of your pieces on Instagram so that your wider network knows about your work.
You don’t have to dive straight into the deep end. Break it into manageable steps and build your confidence along the way.
A friend recently asked me if I found it hard to get dressed in the morning. When I first got into fashion, the answer would have been a resounding yes. I’d spend way too much time agonizing over the perfect pants to match a shirt, the right color combinations, and the ideal accessories.
Now, getting dressed is much simpler. Part of the change is that I prefer a small, curated wardrobe of high-quality pieces that I care for and intend to keep for years.
Another reason is that I’ve embraced the idea of a uniform. By “uniform,” I don’t mean wearing the exact same outfit every day. Instead, it’s about having a reliable outfit template—a guiding structure that makes choosing what to wear effortless.
In Fall 2024, I experimented with Black Ivy style. And while I enjoyed how I felt wearing more formal pieces such as trousers, collared shirts, and ties, I found it impractical and uncomfortable at times.
For Winter 2025, my uniform is inspired by the Japanese City Boy Style. It blends Ivy League aesthetics with relaxed, comfortable fits. When I saw this photo of the Clinch Boots founder, Minoru, in boots, wide pants, and a chambray shirt, it resonated. I decided to adapt his template with pieces from my own wardrobe.
My Winter 2025 wardrobe is:
- Black leather boots
- Straight or wide fit pants
- Oversized button up
Starting a (kinda) New Job
Back in 2023, my manager and Chief Product Officer mentioned the possibility of a Growth team launching in 2024. During my 1:1s with both of them, I asked how I could position myself for that role. They offered advice, shared resources, and I started working on small side projects to prepare. However, to my disappointment, the role didn’t materialize when 2024 arrived.
Fast forward to the end of 2024, during the tail end of planning for 2025, I was notified that my team would be pivoting hard toward Growth. The Growth team was happening after all—just a year later than expected.
Now, I find myself starting my company’s Growth function. It feels like stepping into a brand-new role—a fresh start. The success of this team hinges on my leadership and judgement. This is biggest professional challenge I’ve had in my career so far.
But career challenges aren’t new to me. My career has been defined by navigating tough situations, and each time, I’ve come out on top. This will be no different.
To Some You’re Interesting, To Others You’re Not
It was freshman year of high school. I was walking down the hall when I saw one of the new friends I’d made that week. I waved to her, but I overheard her friend whisper, “You know him? He’s pretty boring.”
For an insecure high school teenager, those words hit hard.
Now? If someone said that about me, I wouldn’t care.
To some people, I’m boring.
But since then, I’ve found my friends, my community, my people. To them, I’m the most interesting person in the room.
And I’ve come to accept that to others, I might always be boring. And that’s okay.
What truly matters is that the people who matter to me think I’m anything but boring.
Social media isn’t inherently bad—it’s a tool. However, it’s important that the tool works for you instead of against you.
This year, I want to be intentional with my social media use.
Here’s my purpose for the social platforms I use:
- Twitter: A learning diary and public notes app
- Instagram: Fit checks and moodboards
- Substack: Distribution and email list
Keep a Work Journal
If you’re like me and have a stressful job, it’s crucial to take time to reflect on your emotions and check in with yourself. Stress can pile up quickly, and without regular reflection, it’s easy to lose touch with how you’re feeling.
My friend Aamir wrote a blog recently that resonated with me: Our emotions are partners, not problems. They’re trying to tell us something. Maybe you’re avoiding a hard conversation. Maybe your anxious about a certain email. Whatever the case, your emotions are partners, not problems.
Journaling has become my way of having a conversation with those emotions. It’s where I listen, reflect, and unpack what I’m feeling. It doesn’t have to be perfect or even consistent every day—it’s just a space to check in.
If you’re feeling overwhelmed or disconnected, try starting a work journal. It could be the small change that makes a big difference.
ChatGPT Helps Me Write 10x Faster
Even though I write daily, my Apple note draft folder has over 1,000 ideas from the past five years.
My biggest bottleneck right now is writing velocity. I’m a slow writer. I can crank out a mediocre first draft quickly—but editing takes me forever.
That’s where ChatGPT comes in. I’m not even exaggerating when I say ChatGPT has increased my writing velocity by 10x. For example, take this blog post: I started by speaking a rough draft into my Notes app. That messy, unfiltered version is my “shitty first draft.” Then, I run it through ChatGPT to clean it up. After that, I tweak it for voice and flow. ChatGPT ensures the content is logical, while I handle the nuance—maybe rearranging a few sections or making the tone more personal.
At first, I felt a bit icky using AI to assist my writing. But I’ve reframed it: ChatGPT is like a partner. These are still my ideas—ChatGPT just polishes them, and I add my voice to make it truly mine.
Don’t Think, Just Do
At the start of an Olive Tree Writing Club session, my friend K recorded a few videos of our group. She spent about five minutes on her phone, then put it away and started writing.
At the end of the session, I checked my phone and saw that she’d posted a full reel hyping up our writing club.
This reel would’ve taken me three hours to make.
First, I’d overthink what to record. Then, I’d take a few videos, probably needing some warm-up shots. Editing would be another hurdle—since I’m not used to reels, I’d have to figure out the process. And throughout it all, I’d be battling anxiety: feeling self-conscious, worrying about putting myself out there, and dealing with my inner critic.
But K did it in less than ten minutes.
It reminded me of how I used to feel about writing daily posts or hosting OTWC events. Both used to make me anxious, but now they’re second nature—like brushing my teeth or taking a shower. I just do them without overthinking.
The people we admire often seem effortless at the things we want to do. But their ease comes from repetition. The friction fades over time, the more you do the thing.
Writing, hosting events, going to the gym—it all gets easier the more you show up.
Right now, there’s friction for me when it comes to taking fit checks or posting on Twitter. But I’m doing it more often, and I can already feel that resistance starting to fade. Soon, I’ll just do the thing, without overthinking it.
As I reflected on 2024, I realized that every major goal I set for myself over the past ten years, I’ve achieved. Getting into my dream school, landing internships and full-time roles, graduating from university, getting fit, eating right, prioritizing mental health, writing every day, solo traveling, moving to NYC, starting a writing community, and diving into men’s fashion—the list goes on.
However, a small handful of goals have eluded me. The first is romantic relationships. The second is growing an audience. Romantic relationships are a story for another day.
Growing an audience is one of my main goals this year. It’s been on my radar for years, but I’ve never made significant progress. One reason is that higher priorities like academics and my career often took precedence. Now that I’ve checked many of those off my list, growing an audience has become my focus.
Another challenge was not having a specific niche. Growing an audience 101 says you need a niche, and it’s true—it makes everything easier. I now have a clear niche in menswear, a topic I’m interested in and enjoy sharing with others.
Putting myself out there has also been a hurdle. It’s not something that comes naturally to me, and I’ve had to overcome personal narratives that held me back. The work I’ve done with the Olive Tree Writing Club has helped me push past these barriers.
When it comes to Twitter specifically, I know the tactics. Over the past five years, I’ve built a strong foundation, and I’ve started tweeting daily. Surprisingly, I’ve been enjoying it.
One major mental shift has been treating Twitter like a notes app. Right now, my thoughts are consumed by menswear, so I simply tweet them without worrying about how they’ll perform. This approach has made the process fun, whereas in the past, Twitter felt like a slog.
I’m playing the long game here, and I’m excited to see where it takes me.
I started writing on January 1, 2020—five years ago. At the time, I didn’t know any other writers.
That changed when my friend Rishi, now an OTWC member, started a group chat in early 2020 with five friends who shared an interest in writing. This group edited my work, held me accountable, and gave me the confidence I needed early on. Through this shared journey, our bond grew, and our conversations expanded far beyond writing.
When I moved to NYC, I wanted to recreate that same energy and find an in-person writing community. When I couldn’t find one that felt right, I decided to start my own with a few friends.
Two and a half years after starting OTWC, I’ve met hundreds of writers in the city. Many of my closest friends in NYC have come through this community, and their drive for writing inspires me every day.
Whether you have a New Year’s writing goal, want to grow your audience, or are working on a book, I want you to experience the same magic I felt. The Olive Tree Writing Club is your community—a place to keep you accountable, look over your work, and get inspired.
For anyone in NYC, we’ll be kicking off the new season of the Olive Tree Writing Club on Jan 12th @ 10am! RSVP here.
What I Love About My Job
This morning, I took some time for a deeper reflection on my career and where it’s heading.
A few days ago, I wrote about wanting to see my career not as a list of jobs I’ve held, but as a series of projects I’ve worked on.
Currently, I’m a Product Manager at a construction tech company. I like to think of Product Management as the art of creating products that people love and that drive business value. In many ways, this process is at the heart of what makes a business successful.
At work, I’m learning how to build a technology-driven business—an invaluable skill because technology can intersect with any passion or interest I have. Every day, I’m gaining knowledge and experience that will help me create my own projects in the future. And the best part? I’m getting paid to learn.
This perspective helps me see the bigger picture and stay motivated. It’s important to remind yourself why you’re doing what you’re doing and remind yourself often. Your “why” might be you believe in the mission of the company, perhaps your role is an outlet for self expression, or this job can be the means to support your family.
Whatever it is, having a sense of purpose makes all the difference. Without it, work can easily start to feel like a grind.
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.
Growing With Purpose
I recently came across a quote from Mark Twain: “Most people die at 27, but we bury them at 72.” During our school years, we’re given a structure that encourages growth by default—there’s always a next step, a challenge to tackle.
But once you enter the “real world,” life becomes a choose-your-own-adventure. Growth is no longer automatic; it has to be intentional. It’s up to you to decide where and how to grow.
This is why so many of my peers around my age experience a quarter-life crisis. It’s a crisis of meaning. Many of my peers have reached a point where they have everything they thought they wanted or needed, yet feel unfulfilled. Growth is essential to avoid this stagnation, but it has to happen in areas that truly matter to you.
By default, the world pushes us to grow in areas like money or career. And for some, that’s exactly what they want, which is great. But for others, pursuing those goals feels empty because they aren’t aligned with their true values.
As we head into 2025, it’s worth reflecting: What areas of your life do you want to grow in that are authentic to you?
Attract, Don’t Chase
During my teens, I began reading and working out. By my senior year of high school, I was always carrying a book, reading wherever I could. Around the same time, I started working out, laying the foundation for discipline and confidence.
In my early college days, I immersed myself in self-improvement. Fortunately, my curiosity aligned with my career aspirations, which naturally made me career-focused. Reading equipped me with the tools for self-education, and working out instilled the discipline to follow through.
I also began prioritizing nutrition—experimenting with intermittent fasting and counting calories to better understand what I was putting into my body.
I introduced meditation and morning journaling into my routine. Writing became a daily habit, and I worked to refine that skill.
Since then, I’ve attracted an abundance of goodwill into my life. I’ve built a high-level circle of smart, kind, and ambitious friends. Opportunities and meaningful connections continue to come my way—not because I chased them, but because I became the kind of person who naturally attracts them.
The goal was never about chasing. It was about becoming who I wanted to be:
Someone I’d want to hire.
Someone I’d want to be friends with.
Someone I’d want to date.
Focus on yourself first, and the rest will follow.
On Daily Affirmations
For the past few years, I’ve been using the same daily affirmation, and its power lies in programming my self-talk. Self-talk shapes your reality, and the best part is—you have control over it. You might as well use it to your advantage.
The end of the year is a perfect time to reflect and come up with a new daily affirmation.
What’s your goal for the upcoming year?
Do you want to be more creative?
Attract someone into your life?
Achieve something specific?
Create an affirmation around that goal and repeat it to yourself every morning. I do this as part of my Five-Minute Journal—it’s the first thing I see and say to start my day.
For the new year, my affirmation will be about continually pushing my relationship with fear. Inspired by Dune, my current affirmation is the Litany Against Fear:
I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain.
What I Like About Oversized Clothing
The other day, I wrote about oversized clothing and whether I actually like it or if it’s just a trend.
More and more, I find myself naturally gravitating toward oversized silhouettes.
In one sentence: for me oversized clothing is sprezzatura—effortless style.
Beyond aesthetics, oversized clothes are comfortable. The extra volume provides greater mobility and breathability.
They also naturally project a casual vibe. One thing I love is the tension created when traditionally formal pieces are given an oversized fit. For example, an oversized button-up shirt—usually associated with a preppy look—feels more relaxed and laid-back when oversized. The same goes for trousers: a formal wool trouser takes on a casual, relaxed vibe when it has n oversized fit. Dressed-up garments with an oversized fit strike the perfect balance between looking polished and showing you’re not taking yourself too seriously.
Write Everywhere
Thanks to my daily writing habit, I’ve started writing everywhere.
My phone has become a mobile typewriter, and I’m constantly in the drafts section of Apple Notes.
I write on the subway, in the car, on planes, or even while standing in line. When I’m out on walks, I’ll often use the speech-to-text function to capture my thoughts.
When I meet people who are just starting to write, I remind them that there’s no excuse not to. Writing is easier than ever these days.
On CP24
CP24 packs all this information in one screen.
I was at Osmow’s today, enjoying the classic Toronto meal: Chicken on the Rocks.
On the TV was CP24. Anyone from the Greater Toronto Area instantly recognizes CP24—a news channel that crams weather and traffic updates, breaking news, sports scores, and stock tickers all onto one screen.
In Toronto, CP24 is the go-to default. If there’s a TV with nothing specific to play, it gets set to CP24.
Growing up, my dentist always had CP24 on in the waiting room. My barbers played it in the shop. At home, it was the background soundtrack of mornings as my parents got ready for work and we kids for school. There’s nothing quite like it. In New York City, for example, there’s no equivalent—a channel everyone knows and defaults to.
Clothes Have Power
Art is a transfer of energy. When we engage with art—whether it’s a painting, a film, or a book—we experience the emotions conveyed through the strokes of a paintbrush, the way a scene is shot, or the rhythm of the words. This transfer of energy is what makes art resonate with us and ultimately what makes art art.
This applies to clothes as well. I can feel the power, the aura, behind a piece of clothing. There’s an energy behind the design, the care of the craftsperson who made it, or the life it carried with a previous owner. A garment carries these experiences, and wearing it allows you to carry that energy forward.
But the energy in clothing can also carry the inverse. If a piece was created with ill intent—through unethical labor practices or careless design—that energy lingers, too. There’s something about those garments that speaks of their origins, even if subtly.
I like to say that clothes have a soul. Care for them, raise them thoughtfully, and they’ll carry you with care. Clothes are more than fabric; they’re stories we wear, energies we feel, and companions in our life.
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