Success happens when they decide to come over and stand at your window for a little bit. You discuss what you both see.

Then, maybe you go over to their window, and talk some more. That can also be a moment of success. What’s most important is that the learning takes place.

An excerpt from my new newsletter, Leading Thinker.

The post Success happens when you teach someone how you think appeared first on Herbert Lui.

To a vinyl collector, this is absurd, and perhaps even heresy. What would a person do with a vinyl record if they don’t plan on playing it?

Participating in music isn’t just about listening to the songs. It’s about connection. When an artist releases music or performs, they make a statement, and in the process they may create an experience that changes a person’s life.

Anyone can access the music today; that’s abundant. Vinyl offers a rare chance to own a tangible, lasting, piece of work to represent that moment; that’s scarce, and tends to become more valuable with time.

Not like a piece of fine art, whether a vinyl gets played until it’s worn out, or remains unopened and framed on the wall, is up to the buyer.

P.S., I recently found out the first thing some visitors want to do after arriving at a Canadian airport is buy an iced cappuccino from Tim Horton’s. No wonder there’s a branded store.

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“No, it’s going. It’s not working,” he replied. That distinction resonated with me. 

Many times, projects and practices won’t produce the results you seek right away. You will need to get it going before you can expect it to start working.

The post Sometimes, it goes before it works appeared first on Herbert Lui.

The thing we all have in common is that we decided that working out at the gym will be the solution to our problems. Now, we just need to actually work out, at a clean place and fair price.

A trainer working at the gym doesn’t need to be an expert at letting off steam, or improving self esteem. They don’t promise you that you’re going to find a partner. They just need to help you work out and achieve your fitness goals.

When you’re looking for ways to start a business, your customers will have all sorts of professional and personal problems. 

If you feel confused, one useful starting point can be to ask yourself what your version of the gym is. What’s the solution that people have decided on? Position yourself accordingly.

The post Shaping a solution appeared first on Herbert Lui.

All that said, we’re not sure what a music website’s role is in 2026 and beyond, but we feel like it’s a necessary piece for Pigeons & Planes to be the brand we want it to be. We’ve always aimed to be a platform where artists could dig deep and tell their stories, where writers could share opinions and start important conversations, where fans could get the context needed to form real, lasting connections with music and a better understanding of the artists they love. A lot of that has been replaced by the immediate payoff of social media dopamine hits but after a while, it doesn’t hit the same.

In other words, knowing the problem, and not waiting for a solution—but actively building towards one. Trusting that you’ll find it along the way.

A person—or group—who writes at a website can get stronger with time, as the library grows, whereas that seems to be the opposite in the case of social media. A website offers a strong foundation, whereas social media is shaky.

The half-life of a social media post is much shorter than the half-life of a publication article. (In other words, consider this question: a month after you post, do you think more people will see your website article or your social media post?) 

Unless you’re extremely organized, it will take effort for you to find your own best social media posts, because paywalls and non-descriptive URLs prevent search engines from indexing it. Imagine how that feels for your readers, who say something like, “I saw a great tweet the other day,” and summarize it without being able to find it again. With a website, you could easily search for your own keywords and dig it up. I have written 1,000+ posts at this blog, and I have never had a difficult time with this.

Depth, as Jacob writes, is another; social media is not conducive to encouraging a reader to focus, whereas you can design your website to be clearer and less stimulating. Compression, by definition, removes depth. 

Because it draws fewer readers right away, a website also allows its creators to take a bit more creative risk—to be more spontaneous and random, too—which creates openings for deeper connections. As J. Cole writes at his blog, “I been wanting a lil blog for years. Somewhere to post random shit I fuck with where the audience is way smaller than it is on the social media platforms.”

It’s great to see a team come back to a website after betting on social media. And even if Pigeons & Planes doesn’t know what the role of a music website will be in the future, I have a feeling that nobody else does either, which creates the unique opportunity for them to help define it.

The post Social media just doesn’t hit like a website does appeared first on Herbert Lui.

Indeed. Hacker News feels like one of the last places on the internet with a semblance of sanity and reality, thanks to its devoted community and many mechanisms devised to catch spam. In many ways, it’s the gold standard, especially in the technical community. 

I signed up for Hacker News five years ago, and I’ve been really enjoying participating. I often submit posts from this blog that hit the front page, and many on behalf of friends as well (because I like their writing, not because they asked). 

I wanted to write this because I know many people are interested in hitting the front page, and I wanted to share some lessons learned and suggest some useful ways for thinking about it. 

The main purpose of this post is to encourage people to spend less time gaming the system, and more time writing articles worthy of hitting the front page. Here are a few of the lessons I have learned along the way:

1. Write articles that deserve to hit the Hacker News front page

The front page of Hacker News is a great place to be, for all sorts of reasons (awareness, clout, etc). There is a great sense of validation that comes from your smart friends saying, “Wow, are you on the front page of HN?!” 

With the audience at Hacker News—people who enjoy hacking—some degree of hacking Hacker News is to be expected. There are even people who write about how they try to game the front page (here are some examples).

Still, to me, the most surefire way to hit the front page of Hacker News is to make something that deserves it. This is necessary, but not sufficient. The XKCD comic, “Constructive,” best describes this in spirit. Nobody will be mad about learning something new and useful, even if you hacked your way to the front page.

What’s a good definition of worthy? My approach is relatively intuitive; I read or skim something, and if I like it, I post it. If I like something I wrote, I post it. I’m aware this topic deserves its own post and I’ll need to write it another time. Here’s a useful starting point though. 

2. Ask for an initial boost, occasionally

When you submit a post, it’s a well known secret that getting several friends to upvote it will improve its odds of hitting the front page. If you want to try this, aiming for 15 people in 30 minutes can work. Try asking people who regularly use Hacker News. 

There are many tricks to this, which you can research on your own (this is a good starting point!), but at the end of the day, this is only an initial boost: in my experience, if the post doesn’t deserve to hit the front page, it will get flagged and removed, or it will drop off very quickly. Worse yet, your post loses trust and may get your account or URL flagged. So, if you must do this, do it only when you feel a strong conviction about an article.

The final destination of submitting to Hacker News is not needing to do it for self promotional purposes. GitLab’s policy is a good example of this, “Never submit GitLab content to Hacker News. Submission gets more credibility if a non-GitLab Hacker News community member posts it, we should focus on making our posts interesting instead of on submitting it.” (See the first rule!)

A skeptic might suggest that GitLab only got to this place by originally self posting, even occasionally, enough that the community follows them and posts independently. (That’s probably why there’s a rule!) This level of focus on writing is something to aspire to, but not very useful for companies and people who don’t have a following yet. 

Something to keep in mind: if your URL is constantly hitting the front page, that doesn’t look very organic. For example, look at the submissions from GitLab; many posts only have 2 to 3 votes, and most did not hit the front page.

Again: Do this very sparingly, if ever. For example, even though I submit my own posts from this blog, I never ask for upvotes. That’s because I want to see which ideas genuinely resonate with the community.

3. For every post about yourself, submit nine good posts from other people

If you’re going to promote your own work, do it only after you’ve submitted nine other posts. Simon Willison gets away with posting his own stuff often, but he seems to be the exception. This is a useful rule for not being too self promotional at Hacker News.

I submit some incredible articles and most do not hit the front page. This is very sobering. It takes the right time and right place. So hitting the front page isn’t always a reflection of your work. 

This sets a reasonable expectation for your submissions. It also develops your intuitive sense of what the community likes, and deserves to hit the front page—as well as how many deserving posts don’t, just because it wasn’t the right time.

4. Give your submission a second chance

Hacker News has a second chance pool, which gives good submissions a second chance to hit the front page. Again, this only works if your article deserves to hit the front page.

Another way to give your post a second chance is to submit it to other forums where the Hacker News community hangs out. For example, if your post hits the front page of the r/programming Subreddit, readers who liked it may submit it to HN, which in effect creates multiple submissions on your behalf. 

This happened to me when I submitted a Figma post to r/programming, and it felt like receiving multiple lottery tickets instead of just one—which improved our odds of hitting the front page.

5. Write good comments, and turn them into posts

Once, I saw a post related to my book’s topic hit the front page of Hacker News. I wrote a comment which resonated, so I suggested that my publishers excerpt the relevant parts of my book into a post. My publisher did that, submitted to Hacker news, and that submission hit the front page. 

I actually think you can take this further: submit an already existing article related to a topic you want to write about, and if that blows up, then use it as an occasion to research what the community thinks as well as write useful comments. Take stock of the most resonant ones and turn those into posts.

Those are the lessons! It’s pretty difficult to game the system, so I have given up trying; instead, this is the advice I offer. I hope that you realize that you’ll need to at least pretend to be a participant at Hacker News. My now not-so-secret hope is you pretend your way into actually becoming a good member of the community in the process.

The post Five lessons for whispering into the Hacker News front page appeared first on Herbert Lui.

Spending energy in this process—finding a story, developing a thesis, pitching it, giving it shape, infusing it with experience and expertise, writing it, editing it, publishing it, promoting it—effectively creating assets that connect the author to the reader, has been such a delight and privilege to work in.

As I’ve tossed my work samples back and forth with prospective clients, I realized this was a good opportunity to publish, not send. Here are a few of the stories I’ve worked on, as well as some of the people and teams I worked with:

2012: A few years after the iPhone introduced apps, I joined Xtreme Labs to help tell stories about mobile apps and product development. When I first signed up, I was still a student at Western, and I clearly remember waking up at 4 or 5am to catch the two-hour morning train from London, Ontario into Toronto. I felt surprised at how many people made this commute.

2013: A prologue takes place at the beginning of a novel, before the first chapter. When I initiated a video interview series with my friends, the questions we explored all took place before our guest artist found success. In hindsight, I was trying to answer the question: How does a person take a leap of faith? I was also looking for permission to take the leap myself. My friends and I filmed the first episode of Prologue with Ryan Lewis at Osheaga. This project would span several years, and we filmed episodes with MC Jin, Casey Veggies, Bishop Nehru, Ty Dolla $ign, and Post Malone. After our episode with Ferg, he said, “That was the best interview I ever did.” A big shout out to the team at Alfredo Films for filming these interviews, which were often arranged at the last minute.

2014: If 97% of all albums sold fewer than 1,000 copies, what could an artist do to make a sustainable living? Ryan Leslie decided to answer this question, starting by building direct relationships with his fans. In order to buy his new album, Black Mozart, you’d need to text him. This infrastructure was supported by Superphone, which was then known as Disruptive Multimedia. This was an apprenticeship where I worked as a marketing strategist, doing publicity, as well as building and writing the first company website. Learning Ryan’s approach would go on to inform how I approached my career as an author. This year, I also joined Gawker Media as a writer in-house for Lifehacker. I found one of my favorite stories near the end of my time there, about how to create your own luck.

2015: Ye was still known as Kanye, and his story had taken on an unbelievable new crescendo; he had just become a dad and husband, and signed a new deal with Adidas that would eventually make him a billionaire. Still, while he was seen as one of the best artists in the world, he was also seen as incredibly polarizing. I’d watched many of his interviews and found his creative insights very useful, so my friends and I published The World According to Kanye. As the years went on, and Ye’s story took twists and tragic turns, I realized he indeed was a teacher—one who practiced the creative process very well, but also showed his students what to avoid in their lives.

2016: I spent a fair part of the previous year and this one working at Connected, then known as Connected Lab, as a fractional marketing leader. The story of mobile app development expanded into the Internet of Things. Amongst many content and publishing initiatives, my team and I organized Canada’s first Amazon Alexa hackathon with over 100 developers (which was covered in The Globe and Mail). 

2017: One of the intersections I’d spent a lot of time at was between technology, business, creativity, and entrepreneurship. I joined Shopify as a deputy editor for Shopify Plus, where I helped tell stories involving ecommerce, entrepreneurship, and enterprises. At the time, the Shopify brand was still pigeonholed as a dropshipping brand for small businesses, which competitors were eager to exploit. I got to work with Tommy Walker, who helped articulate what I felt but didn’t know how to say yet: content marketing and stories were intertwined. He made a document called The Code, which conveyed how he wanted to tell stories for Shopify Plus. I edited every article published between November 2016 and July 2018, wrote regularly (including onboarding content like “5 Things to Do the Moment You Upgrade to Shopify Plus“), and edited case studies, industry reports, and customer product emails that helped show enterprise customers how they could use Shopify Plus. Another document made an impact on me, by general manager Loren Padelford, entitled “Burning down the enterprise.” It conveyed the vibe and approach of Shopify Plus. 

2018: Shopify was a big place, and I took on a separate, concurrent, project to work with the product team to launch a new publication. Shopify needed to hire a lot of product managers, needed a stronger employer brand, and had a lot of stories to tell. I did a workshop with Shopify’s product team, and worked with them on stories exploring the making of Shopify Pay and Shopify Flow. 

2019: Account software was often the backbone of a business’s operations. The thing that caught my attention were the entrepreneurs who were often customers. At QuickBooks, my first real-ish full-time job, I joined as the editor in chief for QuickBooks Enterprise products, where I built and managed a freelance writing program and created product campaign assets including landing pages (example), PPC content, ebooks (#1, #2, #3), and case studies (example). Many years later, I joined a small business that used QuickBooks Enterprise and saw just how integral it was to the finances of the business.

2020: Every year before this, I harbored a quiet ambition to write a New York Times bestselling book. Whatever my approach was, it wasn’t working. I was close to turning 30 without writing any book—let alone one that hit the bestseller list—and I didn’t want to let that happen. So I radically simplified my approach. From March onwards, I spent this year doing absolutely no marketing work, and I wrote and published a book entitled There Is No Right Way to Do This. I wrote about creative blocks because I struggled with it, and because I felt like I had to write it. Of all the copies I sold, many of them were bought by my friends—people who were really fans. This was inspired by Ryan’s approach.

2021: What if a full-time job could support my writing, and ease up the financial pressure? This was a question I was considering when I joined WorkOS, where I helped tell the story of how tech startups could go upmarket. This was a very specific story, one that I was uniquely positioned to discuss from the Shopify Plus and QuickBooks Enterprise experiences. To me, it seemed like a matter of a business’s survival, so it was an important story to tell; it was possible that enterprise customers could make a lot of steady money that supported the business’s riskier product bets. (Independent of this, the story of how meditation app Headspace sold to businesses caught my eye, and I wrote it for Marker.) I researched, produced, and launched WorkOS’s podcast Crossing the Enterprise Chasm. I also worked with many of the tech team members on their stories, including what makes a good changelog.

2022: I spent most of this year living in Hong Kong, where I worked with Holloway to edit the manuscript of There Is No Right Way to Do This and publish a new book, Creative Doing. I sent a digital copy to all my original customers via email. I wrote a lot more about this process here, and here. The only thing I’ll add: I love books as a format, because they can survive without much ongoing maintenance. During the editing phase, I started writing every day as well. I first heard about Seth Godin doing it a few years before; I’d tried this a few times and failed, and I was inspired by Lindsay Jean Thomson and #The100DayProject to try again. 

2023: I moved to New York City and joined Figma as a content strategist on the Story Studio team. I wrote several stories, including this piece on designer-developer handoff to accompany the Figma/Jira product launch, which involved interviewing tech leaders at IKEA, Condé Nast, Turo, and others. I also ghostwrote “How AI will influence creative tools: A conversation with Replit’s David Hoang,” exploring AI’s impact on design and creative workflows. One of my favorite pieces was with Ovetta Sampson, who I interviewed about minimum viable data. As part of Figma’s expansion into developer audiences, I worked as the ghostwriter and lead editor on “What codegen is (actually) good for,” authored by an engineering manager and developer advocate, intended to change how technical leaders thought about codegen. This post hit the front page of Hacker News and sparked a discussion. I became the unofficial in-house Hacker News whisperer on the marketing team, and I helped several other technical posts that reached HN’s front page, including this post from Figma’s databases team, and the authoring staff engineer publicly shouted me out. 

2024: I joined FGX as the marketing director. I wrote the launch announcement, “Introducing the FGX Platform,” explaining complex enterprise logistics features in a compelling, accessible way that supported their enterprise sales motion, and leading to re-engagement from dormant major clients representing six figures in revenue.

2025: I mostly hunkered down on projects I’ll be sharing very soon.

There are so many other stories—big and small—that I didn’t get to include in this timeline structure, and many people I need to link to. I plan on updating this post and adding them as they bubble up in my mind.

The post 10 years of stories appeared first on Herbert Lui.

Or you might have hired some marketing firms in the past—SEM, publicity, social media, etc.—but you haven’t invested in your own website beyond a homepage yet.

Meanwhile, as you build up your lead pipeline, or your past customers are referring you, your prospective customers are asking:

What product or service do you offer? Is it for me?

What proof do you have that your product or service works?

Why should I give you a shot? Who are you and your team? 

What services are you capable of? Which do you want to highlight? 

What’s the ballpark price I can expect to pay?

What’s a good reason I should trust you? What can you teach me that I don’t know already?

These questions are on your customer’s mind, and phone calls are not a scalable solution. Media—in the form of blog posts, whitepapers, videos, podcasts, articles, etc.—are. They’re most effective when they’re organized in one place, in a section of your website like a blog or resource center. You could organize it into a book as well. 

If you’ve done publicity and social media and podcasts here and there, taking a couple of hours to collect them all and list them out at your website (or republishing there) is worth it.

(I recently initiated a foundational content project for Obello, which I discuss more here.)

The post Foundational content appeared first on Herbert Lui.

Projects like Creative Doing, pretty much all my writing online (including Medium), Prologue, The World According to Kanye, Chamath Archive, Revision, etc., were all made possible by my business writing work. In other words, my business writing cross-subsidized all of these creative projects. The lack of financial pressure felt very liberating for each of these projects; however, my next focus is to structure these projects so they can sustain themselves. (I believe I discussed this with Chris Do at The Futur.)

The gatekeepers—publishers, etc.—don’t offer as much distribution support as they used to. They also lost control of their audiences; now, in order to work with them, you need to bring the audience. (The good publishers still offer credibility, production efforts, publicity, etc.)

There were personal reasons, too. I was initially constrained by not knowing the first thing about pitching traditional publishers or distributors, and I hadn’t met any agents, and I could just publish my work on the internet, so it felt easier for me to do it myself—which I did.

In this season of exploration, I’m returning to independently working with companies. Some of my recent projects that have gone live:

• The team at Obello hired me to help them set up their writing and marketing foundation. Tangibly, the project included a blog post to develop thought leadership, a blog post to support their launch from closed beta to general availability, an email to their product waitlist, and the first part of their whitepaper. From a strategy perspective, I delivered through processes beyond AI’s current abilities: identify and decide which deliverables would have a high impact, ask good questions and share creative research to elicit interesting ideas, and edit drafts for development and structure.
• The team at Greptile hired me to salvage an initial draft of a blog post they weren’t sure what to do with. That turned into this post, which sparked a lot of discussion at Hacker News. I’m now working with them on the next post. (I have very limited capacity to work on a per-post basis.)

I’ve always felt enthusiastic about technology (my first blog as a teenager was about tech!), so I’m glad to continue this practice. On the independent front, I’ve worked with organizations like Shopify (here’s a case study, and a deep dive), Flipp (case study), and the City of Toronto (case study). On the full-time front, I’ve worked with Figma (lots of blog posts here), FGX, WorkOS, and Intuit.

The post A return to my business writing practice appeared first on Herbert Lui.

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.

The post Reflecting on my failure to write a NYT bestselling book appeared first on Herbert Lui.