In the release notes, you’ll find a 10-page original manga, hand drawn by graphic designer Melanie Schmidt. She writes, “Every line was refined digitally before I switched to analogue for the shading, because apparently I enjoy making my life unnecessarily difficult.”

Going beyond requirements is a gamble. While it can feel tough in the moment, you’ll at least have a three dimensional business card you can point to. And sometimes, like this time, it really works. 

Remember, as Hank Green says, “You aren’t just working on the thing you’re making right now, you’re also working on everything you will ever make in the future.” The reward for doing this work well is more of this type of work.

If you’re a manager, giving your team the freedom to be extra creative is a very simple way to make them feel fulfilled and to get some extra attention for the business.

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A lot of other stuff went on though, and here’s one of the stories (I recently shared at LinkedIn as well):

Three years ago at Config 2023, Figma had just hit the front page of Hacker News with 500+ upvotes. My boss’s boss found me and asked, ‘How did we do it?’ I blurted out,

“I don’t know!” The blog post my coworker wrote was great, and my mind went to how much care our team put into it, so I added, “The content was really good!”

Everyone cheered. I felt strange about it, accepting credit when I felt I had little influence on the impact. Then again, this wasn’t the first time it happened.

A month before Config, I submitted one of Figma’s earlier blog posts to Reddit. Someone cross-posted it to Hacker News, and those few clicks turned into tens of thousands of pageviews, ending up the 4th most popular Figma post of 2023. That success led us to try hitting the front page with Config’s Dev Mode launch.

Over the next year at Figma, I paid close attention to better understand how these lucky outcomes happened. I worked with our team to hit the front page of Hacker News 7 more times. More recently for my client, Greptile, I’ve ghostwritten 3 blog posts that have also hit the front page.

One way to think about luck: It’s what we call positive outcomes when we don’t understand the causes.

If someone were to ask me again, I know now the honest answer is we wrote a clear, useful, blog post and shared it with people who needed it. The distribution side is its own craft as well, which I’ll write about more in the future.

Organic growth feels like luck because there’s less you directly control. What you can do is influence the conditions. The biggest constraint on that influence is the quality of the writing itself.

You can execute on content distribution (e.g., submit something to HN, post it to r/programming, or email it to readers) and none of that matters if the writing isn’t at least useful to the people reading it.

I now work with content and growth managers at AI dev tool companies on exactly this problem: writing executive content, ebooks, reports, product announcements, blog posts, and helping the work find the audience that it deserves.

That’s what led me to set up this distribution workstream. There’s a lot more to write about, including how I think about distribution these days (including finding spaces to discuss ideas, and selling 5,000+ copies of Creative Doing).

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TL;DR: When you start a new blog or publication, your metrics will disappoint you. That disappointment leads to doubt, and often kills a content practice before it has a proper chance to make an impact. A more useful signal in the first few months is author satisfaction, and it’s something you can actually pay attention to.

I write about content strategy, and I’ve helped companies like Figma, Shopify, and QuickBooks build it. This piece is about an early part that usually gets overlooked:

In my first few weeks of high school, my gym teacher took our class outside. Amidst a backdrop of changing fall colors, he paired us off to practice throwing and catching footballs. 

My partner threw a football that didn’t make it to me. I ran to catch it. It bounced up off the ground at an awkward angle, in the strange way that footballs do, and the sharp end hit me right between the legs. I’d been punched in the stomach before and had the wind knocked out of me, I’d also been hit in the forehead with a volleyball pole, but this felt way worse. I got up and pretended I was fine, to avoid drawing attention, but in the back of my mind, I wondered if I’d need to go to the hospital. (No, it wore off, and I was fine.)

Early into kicking off a content practice, clicking into your metrics feels exactly like that. You publish twelve blog posts in a couple of months, and you click into Google Analytics, and the low numbers make you feel shook. You put on a brave face, but you wonder, is this project actually going to work? Is it worth my time to continue prioritizing this?

Pageviews are a common dimension of success. It’s a signal that people are actually reading the content. (I say “reading,” but you can substitute “viewing” for videos or “listening” for podcasts.) It’s easy to understand and measure. More pageviews are generally better. Going viral is “good.” 

But early on, even a leading indicator like pageviews, or a lagging direct measure like sign ups, aren’t signaling the underlying progress you’re making. 

There are many reasons people in companies decide to establish themselves as leading thinkers. For starters, it’s good for business. When you have a reputation, prospects trust you and you can close deals faster. You stay top of mind with them, so your business is on their consideration list when they’re in the market. The list goes on… (Easier to recruit people, creates a halo effect for your future products, a more reliable marketing channel for you, not so reliant on paid ads or platforms, getting publicity is easier, etc.)

David Heinemeier Hanson is a leading thinker. Known more widely as DHH, he’s the CTO of Basecamp and co-author of several books. A few years ago, he started a new blog. After writing a few essays, he started checking his metrics, and realized almost nobody was reading. He decided to stop. He says, “In the beginning, it’s always disappointing.” This period of disappointment is more often the case than not, even with prominent leading thinkers like DHH. He says:

“The only way to get through that is this authentic yearning to just talk about what you’re doing. That’s the other thing that I found makes it so much easier, is if you stop setting the goalpost of, “I’m doing this because I’ve got to promote the business [or] because I’ve got to grow it. I’m just going to talk about what interests me. I’m going to write to me… as though I was a reader, and if I was watching someone else, this is what I would want to know. Then it’s a lot easier. It’s like a journal. You stop caring so much about those specific outcomes, and suddenly it starts feeling like there’s a human on the other side and that is probably the only way you’re going to connect to anyone these days if you’re not shoving it down their throat with ads.”

As a result of this shift, DHH shifted his focus away from metrics and towards the writing process. He wrote hundreds of posts in the years since, and finally reached a number of people he feels good about. 

DHH uses the words, “authentic yearning,” to describe what I would call author satisfaction. Tyler Cowen, who writes every day at the most popular economics blog in the world, describes it in a different way, “If I keep on doing it, I figure I’ll get somewhere with my writing and most other people don’t find it that fun. So, it’s a competitive advantage just to be choosing things you’re intrinsically interested in.”

This experience of satisfaction feels different to DHH and Tyler, and it’ll probably feel different to you as well. It isn’t as clear, tangible, or easy to measure as quantitative metrics like pageviews or sign ups. But I think it’s much more useful as a gauge of early success, as well as a signpost for whether you’re heading in the right direction or not. 

With practice, you feel a clearer sense of what satisfaction means to you. I recently interviewed a co-founder of a company with seed funding for a blog post. In our first meeting together after I sent him the draft, he said, “Wow, Herbert, you made me sound so smart!” That, to me, can also be how satisfaction sounds like. He even volunteered to cross-post the article to LinkedIn.

Satisfaction is tricky to measure; it’s more useful to evaluate it. Measurement is about getting specific dimensions, like pageviews and sign ups. Evaluation is about finding the value of something; appraising it. While metrics may provide you with dimensions to inform your judgment, they don’t replace it. Startup advisor Shreyas Doshi describes it like this, using the analogy of parenting: you don’t have metrics to tell whether you’re becoming a parent, but you can tell you are by evaluating it.

Similarly, if you’re a growth manager working with your team members on content, you need to evaluate how the authors feel after they publish their work. Here are some aspects to consider:

• Process: Do they enjoy writing it themselves, or do they prefer working with a ghostwriter? 
• Expression: Did they say what they wanted to say? Do they feel like they represented themselves and the team well?
• Further actions: Are they volunteering to share the post link to their network? Do they show interest in publishing again? Are they sending you more ideas and drafts?

And of course, you can ask yourself these questions as well as you write your own material.

Success in content strategy rarely shows up in the form of clearly defined metrics. It’s more useful, and reliable, to start with keeping author satisfaction in mind. 

In the previous edition, I suggested that content strategy success is the sum total of teaching someone how you think. When I think of my favorite teachers, they didn’t just try to go through the motions; they aimed to transform their students, which evoked a sense of satisfaction in themselves. They related to students using their own lives, or selected reading material they felt enthusiastic about. That’s the type of satisfaction you can measure success with.

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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.

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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.

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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.

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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.

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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.

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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.

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