Over a decade ago, I attended a charity gala at The Spoke Club in Toronto. I was wearing a tailored suit, having a great time with friends, and, after a couple of glasses of bubbly, feeling celebratory. My career was off to a strong start. My articles went viral at Medium and were picked up by the press. I interviewed one of the most popular artists of the year. I’d started my own editorial studio and worked with tech companies. This was just the beginning, I told my good friend, “I’m going to become a New York Times bestselling author before 30.” His eyes widened. We toasted to it. I felt like I was winning.

While that attitude might’ve helped me find early momentum, it didn’t sustain it. The articles stopped going viral at Medium, for all sorts of reasons. I grew discouraged and nearly stopped writing. My editorial studio needed a lot of work in order to maintain. The years passed by quickly, and while I started and sputtered, I never wrote a book. Not even an initial draft.

I put together a couple of outlines; one for a book entitled the Distraction Drug, another about creative sprints through constraints. I even accumulated a half-hearted set of drafts of a memoir that I didn’t have enough experience or skill to write yet. None of these activities were the same as writing an actual book, though, and while I wrote articles to build my audience, I didn’t get busy writing a book. Instead, I looked for shortcuts, like trying to find a way to ghostwrite with someone famous, so I had a better chance at hitting the bestseller list. I also indulged in distractions, dabbling in different creative projects. I earned money so I could travel, and live on my own. I have written, and cut, hundreds of words describing these experiences in detail, because they felt tangential to this post; perhaps another time, perhaps in the memoir.

In late 2018, as I was about to turn 27, I signed a contract to work an 18-month temp full-time gig that paid me too much money to say no to. I would write and edit for a brand, and start up a couple of writing teams on its behalf. When I shared my salary with some friends, some said cheers, others were in disbelief. I, once again, felt like I was winning. I felt grateful to the person who made me the offer, a friend and previous client. As the months went by, I realized the work wasn’t what I wanted to do. It was a good, respectable, job; yet the perks—salary, prestige, the work itself—didn’t give me energy.

At the same time, my writing had slowed to a crawl. I was barely publishing anything. I felt like writing made no sense. I’d thought myself into a rut, where I felt torn between chasing what I thought the market wanted, and what I still wanted to write, and I struggled to find an overlap. I also felt discouraged at the loss of momentum, as Medium sent less traffic to my posts; I felt like things were hard. In hindsight, I didn’t even know what hard meant. I was being impatient.

At the end of the gig, and the onset of the pandemic, I decided I wasn’t going to take on any paid freelance or full-time work. I was going to try to make it as an independent creator. After a couple of months of floundering, and a nudge from my parents, I decided to write a book; not the one I’d always wanted to write, but just any book. Whatever I was doing wasn’t helping me write the book, so I just stopped chasing the feeling of winning and focused on the work.

When I was writing it, full-time, I was 28 and under no illusion that I was winning. There was not a hair of a chance it was going to make the New York Times bestseller list. I had no agent, nor did I have a deal with a prestigious publisher that offered me an advance payment as I’d dreamed it would. I was just going to put the book together and sell the PDF online. So that’s what I did, and There Is No Right Way to Do This came together just after I turned 29.

At best, the book was a very minor success. Even though publishing the book was a relatively major career milestone, and a reputable publisher made me an offer to work together, I felt even less like I was winning than before I’d published it. There were many nights when my sleep fragmented hours before the sun rose, and I threw myself into the trance of ambition and started to work; but the book’s business model required a lot of readers, more than I had, in order to replace my income. 

At that point, I wondered if I hadn’t bet on myself enough. How could I win if I didn’t fully commit? The narrative, to me, was that history was full of great people who endured years, even decades, of poverty in order to make time to dedicate to their craft. That’s what it took to win. None of those years must have felt like winning, not to them; they wouldn’t have known how it would turn out. 

I considered selling my modest stock portfolio and buying more time to sell more books, and evolve the business model. But this went against every instinct I learned in business school, and perhaps even every instinct I was born with. My parents had endured poverty in their childhood, and their parents before them. It took two generations, but they made it out. Selling my stocks felt like selling my future; such an aggressive pursuit of being a writer meant, to me, like I was throwing all of their hard work away. 

Even if I succeeded, some New York Times bestselling authors are broke; that never felt worth it to me. I realized, maybe I’d defined winning the wrong way, and my feelings about it were deceiving me.

Meanwhile, I continued to feel even less like winning—almost, while putting on a brave face, resigning myself to losing—and I eventually took on another full-time job. It helped alleviate the financial pressure, and while I didn’t feel a meaningful sense of success or prestige, I felt free to write more often. As I said in an article for Mic, “I thought succeeding as an author meant doing it full-time, or at least without a full-time job, and I was totally wrong.” 

In 2022, that book turned into Creative Doing, which I got to revise and edit while I lived in Hong Kong. After I published it, I got to discuss it with a lot of interesting people. Readers enjoyed the book, and worked through their creative blocks. I felt like I was, finally, taken seriously as a writer. My former employer put it up on its book wall. So, while I still failed to make the NYT bestseller list, my writing helped me connect with people at a deeper level. These aren’t small consolation prizes; they continue to resonate with me, years later, in ways the money I earn from my other work does not. I wonder if setting such high expectations of myself was that wise to begin with; if I could go back, I’d tell myself that just writing a book that I was genuinely interested in would have been more than enough.

With hindsight, I can see a little more clearly that my drive to win—my ambition—was an instinctive reaction to constantly being talked out of doing what I wanted. I wrote this earlier: my parents and grandparents grew up with very little. Survival was the goal, and opportunity—a chance to work hard and prove yourself, and the anxiety that came with it—was a luxury. Dreams, betting on yourself, and cultivating a healthy sense of pride, were lessons I could only learn later in my life, outside of the four walls in which I grew up. Aiming to appear on a coveted list was just a lesson along the way, the first of many.

Still, sometimes, I wake up at 4AM, and my mental chatter stirs up the feeling of inadequacy; my mind tells me, in fancy, smart, words, that I’m a loser. The thought that comes to me is a realization that, “It’s too late for me to win.” This feels honest. I wonder if I’d focused harder in my 20s, if I’d worked harder, or if I’d written more and built up a bigger audience—maybe things would be different. Maybe I could write, and earn around what I earn at my job now. I know people who do it, so I know it’s not impossible. And I, sometimes, spend hours working through statements like this.

Usually, I write one statement out, like, literally, “It’s too late for me to win,” as if it were a math equation in my private journal. Then, I start working through four questions, which I found through Byron Katie’s book Loving What Is, which I’ve reworded slightly:

• Is it true? 
• Is there a way to know if it’s true? 
• How do I feel when I believe this statement? 
• How do I feel when I let it go? 

In one of these entries, from a few months ago, I realized that while it’s taken longer for me to win, there was no way to know if it was true if it was, in fact, too late for me. There are plenty of people who did great things later in their lives. I realized when I believed it, I felt stupid and discouraged to the point of giving up. I got upset with myself. Then, I approached my work with aggression and thrash. 

When I let the statement go, though, I don’t feel stupid anymore. The tension lifts, and I can relax. I trust the process more, and I feel like whatever I’m doing is the right thing. I remember I’m taking steps to success. 

After responding to the four questions, I flip the statement around a few times, usually turning a word into its opposite. Then I start turning the statement, “It’s too late for me to win,” around, to see how the new one feels.

“It’s perfectly on time for me to win,” I start. That one doesn’t feel quite right. Rather than focus on the timing, I choose to flip another word; the word, “Win,” is the next candidate.

“It’s too late for me to lose,” I try again. Huh. This one feels right, because I haven’t lost yet. I am still, very happily, writing every day. I wrote a book and published it; one that’s now sold thousands of copies. I have built a skill for promoting it, including helping it get into an actual bookstore, which meant I could do it again without anybody else’s help. I don’t feel like I’m losing, I feel momentum. I realize, also, there’s no definition for losing—that it’s a feeling—and, by extension, there’s no definition of winning, either. This whole time, it was just a feeling.

I define losing: it means quitting writing and giving up. It means self-destructing. It means not showing up, not writing from the heart, letting a ghostwriter or generative AI write for me. Even though I’ve sought out full-time employment, I am still doing all of that, so I’m not losing. Could that mean I’m winning? Have I been winning this whole time? Why hasn’t it felt like it?

My original statement, “It’s too late for me to win,” has lost its grip on me. “It’s too late for me to lose,” is the new statement in my mind, and it’s very useful. I feel energized to do one more turnaround:

“It’s too early for me to win. I am early.” This one resonates just as much as, “It’s too late for me to lose.” It reminds me that images of success from other people—the feeling of winning—doesn’t define what success means to me. What sounds more realistic: that success happens early to more people, or late to more people? I’d wager the latter, similar to how the average age of a successful startup founder is 45. With this story, it feels easier to trust myself; to use what I’ve been given or earned, to focus on me, and to feel a sense of gratitude.

The best time to write this post would have been after I wrote a NYT bestselling book, because that’s what winners seem to do. They write about their losses after they win, and it makes the victory even sweeter. I still haven’t achieved that yet; I’ve shifted my focus away from the feeling of winning. 

Instead, I want to focus my whole self into the actual writing process. I’ve learned to trust this process, and know that good things will happen as long as I keep working at it. I don’t know what those things will be, and I’m totally okay with that. Making a good friend’s list of favorite books this year is very satisfying; so is being linked to by another book or blog post. Hitting the front page of Hacker News is always fun. These outcomes aren’t the point, they emerge as long as I continue to write. When the sense of inadequacy rears its fangs at me, I know how to respond now; not with aggression, but with introspection and a sense of soothing, and a reminder that as long as I’m writing, I’m winning; lists be damned.

If my 25-year-old self read this, he’d think I was quitting. Then again, he didn’t know much about the world, or about creating a life. He’d just moved out of his parent’s house, he wasn’t married yet, nor had he lived in Hong Kong or New York City. He hadn’t yet learned to accept himself, he’d only recently learned how to dream, and his self worth became tied to achieving his goals. His ambition was the only fuel he knew how to use. As I look back at the young man I used to be, I feel grateful for a chance to tell a new story, one that hasn’t squashed the fun out of the writing process and, more broadly, out of life.

I love writing, and I take the privilege of writing here every day seriously. I love books, and I want to write dozens of them, with my own hands because that’s kinda the point. I’ve shaped this game of writing intentionally, to be softer—something I can’t fail at, where winning means I get to play again. In a strange way, I’ve developed both a practice and a sense of resilience—that I don’t need money, prestige, or good things, to happen in order for me to write—as well as a sense of precursive faith. I trust myself; that if I keep writing, good things will happen.

Afterword: When I was searching for this near complete draft, to make yet another final change, I came across a second document with this same title. I realized that I’d outlined this post before, in 2023. Same introduction, same transition, same bit on Creative Doing—which was the conclusion. Isn’t that amazing? My brain had not only outlined this article before, but made so much sense of it, or subconsciously remembered it, that I typed it out fresh, again. Writing is, truly, marvelous.

It was just as pleasing to me to notice that I hadn’t lived out those journal entries yet, or asked myself the four questions yet, so of course I couldn’t include that part of the process. I’m glad I could share that, and I hope it offers you some relief as it did to me. I’m sure that in another three years, I will have more to say about this topic. The story continues.

This post started because my friend Hamza encouraged me on our podcast New Material to share an entry from my private journal.