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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The same thing has taken place with paying for your groceries. You used to need to line up at a check out counter and have a clerk scan items for you and add up the total bill.  

Then, a new product hit the market: the self checkout kiosk. As a customer, it enabled you to scan your own groceries and pay for them. 

These self checkout kiosks required fewer clerks, less space, and were simple enough for most people to use. Grocers that installed these kiosks also set the clerks up to train and educate customers who felt confused or intimidated. 

At first, self checkout sounded ridiculous. “I’m going to do the extra work of scanning my own groceries? No, thank you.” If you had a couple of items, and the regular checkout had a long line, maybe you’d try it. Then, as time went on, you got more comfortable with checking out yourself—and you might’ve ever preferred it. 

Serving yourself was faster, you could take responsibility for any mistakes you made, and you didn’t need to make small talk with anyone. 

Scale used to be a fuzzy concept for me. When I was tasked with scaling distribution for Figma’s Story Studio team, I wasn’t sure how to think about it. Then, I noticed how grocery stores had scaled the selection and checkout processes, and it all clicked for me.

My customers (my co-workers) had an incentive: they were already writing articles, and they wanted to make sure each one reached more of the right readers. They were also extremely busy, so the solution needed to be very simple and low effort for them. A product I made was a list of channels, which looked like a menu—but this was too complicated on its own. In order to make it more convenient, I also introduced a service, a bi-weekly distribution workshop, which would help my customers execute on ideation and promotional tasks.

If you’re wondering how to make a greater impact, or if you’re ever tasked with scaling something, it helps to consider how to help someone serve themselves—or at least get much closer to it. You’ll need to introduce products and services that they feel comfortable using, and educate them on the possibilities and how to use it. It takes a lot of thought, intention, and energy, and it’s totally worth it.

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Out of all of these possibilities, a recording artist needs to decide which one tracklist represents what they want to say. They do this by using an organizing principle. 

For example, choosing to end the album on a sad song might tell a tragic story, whereas ending the album on an upbeat note might convey a redemption story. The same songs, arranged differently, will send a different message. Which message does the artist want to send?

When you’re talking about music, and someone asks, “Who is your top five?” you need to order your favorite artists into a list, the simplest way to apply an organizing principle. When you do this, you’re using an organizing principle based on the reasons you like an artist. When they respond with their top five, they’re also using an organizing principle—according to their values and philosophies. Together, you are getting to know each others’ values through your organizing principles. 

Anywhere you experience a sense of order, you are feeling someone’s organizing principle. You can see organizing principles everywhere, including in cities, art exhibits, books, films, laboratories. 

Wes Anderson likes to anchor his films in organizing principles from other media. For example, he arranged the stories in The French Dispatch with the organizing principles of a magazine. I find thinking metaphorically in terms of articles, magazines, and a table of contents to be very helpful. 

This blog post has nine paragraphs. What made me arrange this paragraph to be here? Why is this sentence third in this paragraph? You need an organizing principle to answer these questions well. Sometimes, even with a clear organizing principle, the arrangement might only work after a few tries. 

An organizing principle is successful when it makes the work say what you wanted it to say. It can sometimes feel incredibly abstract. Virgil Abloh describes “tourist vs. purist” as one of his organizing principles.

When you’re consistent with your organizing principles, you’ll develop a signature. If someone else can recognize your work or imitate you, you’ve done a good job.

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If we agree that’s the core loop of a business, then it makes sense to keep as many customers as satisfied as possible.

That means delivering the product or service as intended, and constantly improving or refining it. It means being reliable and earning trust. It means delivering whatever’s in the scope of your project, even if it’s taking longer than anticipated, and that means eating into margins. It means dedicating time and energy to make sure the service or product is delivered, even if the customer is wrong or another service provider failed them. 

It also means cultivating these stories into team and company lore. Here’s one from Figma:

Coda was Figma’s first paid customer. The story goes after Figma’s and Coda’s teams met for a meeting, presumably to make sure Figma was set up properly, Coda emailed Figma to say the fonts broke and that they’d need to try again in several months. Figma’s CTO turned around and drove back to the Coda office to help them troubleshoot the problem (which turned out to be a networking error, not a Figma problem). Figma didn’t just make a great product; it demonstrated a clear commitment to its customers.

These stories from the past will help guide you and your team’s behavior in the future.

Thanks to Peter Kang for the reminder.

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In other words, if you’re making something new, planning too far ahead will likely just get you stuck. Claire’s approach feels like textbook effectual reasoning. She describes an example using Figma’s annual conference, Config:

We had talked about doing a conference for years, but we were overwhelmed. So step one was to commit and book a venue. (Too small, it turned out—thousands applied, forcing us to change venues two months out.) Then we had to figure out our speakers. What to do… aha source from the community. And too many people applied, who should attend? Make the application annoying enough to filter for the truly excited. From those choices, our strategy became clear: for the community, by the community. But if we’d waited to get it perfect on paper, it never would’ve happened.

This feels right to me. You commit to a goal, then you use whatever resources you have to make it happen. Strategy emerges as you bump into the constraints. 

When I was tasked with figuring out distribution for Figma’s Story Studio, I felt really confused at first. I knew how to do this at an article level, of course—but how could I scale it? What did that even mean? I asked around, and nobody was sure. 

I first tried figuring this out on my own. I wrote documentation that nobody else wanted to read. I tried finding a place for it in our other group meetings. I added a checklist to our article templates. Nothing really stuck.

Eventually, the breakthrough came in the form of a bi-weekly Distribution Workshop meeting that I set with the team. Once those 30 minutes were on the calendar, I had to commit to making the most of our group time. 

I showed up with articles selected and outlining different channels we could promote through. We eventually made the meeting better—let’s invite recurring guests, let’s post thought starters for what we could do with each channel, and let’s use most of the time to generate ideas. I would drive and triage all action steps after. 

Committing to kicking off that meeting, and promoting two articles every couple of weeks, made things happen.

The momentum that comes from committing and focusing on one challenge at a time—the one that’s in front of you—keeps you from worrying about the dozens of challenges that might happen.

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This quantity was a really helpful anchor for when I start applying to jobs. Fadeke had started up a spreadsheet to help her keep track of her progress, so I did that too with Airtable.

I looked for jobs pretty much full-time. In 2 months, I applied to 18 jobs. I did four first round interviews. Two of these opportunities became more serious prospects. One of the companies couldn’t hire me as soon as they had thought, and so I ended up doing a contract with them so I could just start working with the team.

I went through six rounds of interviews with the other opportunity, and I got an offer to join. That was Figma.

So my approach turned out to be, pick a few opportunities, and go all-in. In hindsight, I think this worked because I didn’t apply to that  many jobs—not in spite of it. Because I applied to relatively few jobs, I prioritized very carefully and intentionally. Every couple of days, I looked for new opportunities and put them into Airtable. I caught up with friends and acquaintances.

I often put at least a couple of hours of effort into a job application. I researched the company and let the recruiter or leader know where I saw the opportunity to contribute. I prioritized the opportunities where I could find someone to refer me to the company. If I couldn’t, I would apply and reach out to the person who I thought was hiring. One of the hiring managers told me she got over a thousand job applications and I was the only one who emailed her. That’s how low the bar is.

I also practised my interviews thoroughly. The recruiter would let me know as I progressed what the interviews would be about, and I made guesses as to what questions I would be asked and prepared very thorough talking points. I prepared questions to ask each person who interviewed me and had a look at their profiles to see if we had anything in common.

I rehearsed each answer while I recorded myself, and I listened to how I sounded and refined my answers accordingly. I prepared for each interview and I spent a lot of time doing the take-home assignments.

None of this would’ve been possible if I applied to over 50 jobs in that time span. I wouldn’t be able to put intention into each application. Quantity would not have worked in my favour, because I wouldn’t have improved the quality of each job application. 

This is the type of principle that my friend Michael Karnjanaprakorn is talking about in his latest post, which is about how to get a job at startups. There’s some great specific advice there, and I think the general principle is picking a few opportunities and going all in. The key is feeling out how much is enough. Too few and timing may not work out, but too many and you won’t stand out.

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When Windows Longhorn was out in beta, I spent many afternoons trying to get it to work too—even partitioning my hard drive to figure it out. My cousin was very savvy with computers, but he never understood why the interface mattered so much to me. I started dabbling with trying to install Mac OS X on my PC—known as a hackintosh—but I gave up when I realized that I didn’t want my computer breaking every time I got an update. It wasn’t worth it. I liked the simplicity of the Mac.

I couldn’t explain this very well (and, clearly, I still struggle to). I enjoyed finding high-resolution album art for my favorite songs. Well-designed software just feels good to use.

I recently came across an mp3 file I wanted to listen to, so I started searching for a music player on iOS. I came across Doppler and gave it a try. I really, really, like how simple it is. It’s the complete antithesis to Spotify, Apple Music, and the era of streaming.

When a song ends, I don’t have to worry about another random song coming up. There’s just silence.

All of a sudden, I have started listening to a lot more MP3 files. I had a reason to listen to that audiobook I’d bought a few months ago, as well as my old Prologue interviews. I’m not sure this habit will stick, but I’m noticing how my behavior has changed very quickly as a result of this software.

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Rather than worrying about how you come off, focus on being intentional instead. You want to know—and articulate—what you’re looking for and, just as important, what you’re not looking for. 

In terms of actually reaching out, here are some things I did when I was job hunting:

1. The classic referral

Find the job post and work backwards from there (e.g., is there somebody I know (1st connection) or somebody who knows somebody I know (2nd connection) on LinkedIn who works at the company?).

If I knew the 1st connection, I’d reach out and ask if they were comfortable referring me to the company.

2. The forwardable email

If it was a 2nd connection, I’d reach out with a forwardable email and ask if they’d be able to forward an email and make an intro if they received a positive response.

3. Job hunting as an occasion

I made time to catch up with good friends. It felt energizing to get the moral support, with the added bonus that sometimes they knew people working at companies looking to hire. For example I would eventually get a job offer from Figma and that was because a good friend’s partner worked there and was glad to refer me. I hadn’t even heard of the opportunity before we talked.

4. The weak ties

I also made time to catch up with people I didn’t know that well. Since I spent most of my career running an independent editorial studio, this mostly consisted of past clients or prospects. There’s a classic piece of research that suggests that people who you don’t know well probably are exposed to a very different network to you, and will come across very different opportunities. The conversation would be an opportunity for us to catch up, and I’d talk about being open to job opportunities. I particularly reached out to people who I’d noticed just started new jobs, since the job hunting process was still fresh on their minds.

You could probably abstract these a level higher and apply the principles towards reaching out to your network for all sorts of opportunities. 

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To do this, you might find it helpful to channel a creative vision through a clear structure. 

One example: at Figma, I was involved in a transmedia project covering speculative AI (a big topic!) that spanned multiple channels including a gallery installation, a set of interviews, and a press campaign. When my manager Amber saw me wrestling with the complexity, she made a really helpful suggestion: what would this look like if it was just an article?

The structure of the article made it possible to answer the simple questions:

• What would the headline be?
• Who would you interview for this article?
• What is the thesis?
• What is the lede? 
• What are the sections? 

The idea was for me to bring the answers to these questions back to the transmedia project, with much clearer next steps.

While the project didn’t work out, I often find myself coming back to Amber’s advice. 

Since I’m a writer, I chose an article format to help clarify the vision. If you were a recording artist, you could choose the structure of a song.

The more familiar you are with the structure you choose, the more concrete your vision will become.

As writer and community builder Lindsay Jean Thomson says in Creative Doing, “Your creativity needs enough structure to support your freedom, but not so much that your freedom feels stifled.” 

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• New Material, a show where Hamza and I discuss creativity and productivity, through a business and hip-hop perspective. 
• Three Thought Starters, a newsletter that replaced my old one. It’s currently on hiatus.
• Marketing initiatives for my book Creative Doing, including its first brick and mortar appearance at BookCulture’s Long Island City and Columbia University branches, as well as its first BookBub campaign, and its first Hacker News appearance. 

I worked at Figma as a content strategist (I wrapped up my gig there in June), here are three projects:

• I started a distribution workshop practice at Figma, which looked like bi-weekly meetings to make it easier for the Story Studio and its collaborators (e.g., social, partners, email, comms, etc.) to launch and promote upcoming articles. I also wrote up a full menu of tactics and would kick off each session with ideas to help energize the conversation. There’s a lot more worth writing on this one. One of the more wide-reaching launches was this post on databases, which earned a hat tip from my coworker Samantha Steele.
• One of my final projects at Figma was to work on its zine, The Prompt. I did this interview with Ovetta Sampson on the topic of minimum viable data. Lots of double checking and proofing efforts as well for the print version.
• A handful of other articles with Figma: I interviewed Peter Yang and co-wrote this one under his name, as well as summarizing an interview with David Hoang. I also wrote this feature for the Jira for Figma launch.

I joined FGX as its director of marketing, here are three projects:

• One of my first projects at FGX involved the launch campaign for the FGX Platform, which we announced through this post, LinkedIn, and emails to customers. I kicked off the drafts, made recommendations on strategy, and worked closely with James Wong to polish all of this.
• I refreshed a couple of strategic, product-centric, blog posts, such as this one comparing FGX’s services to those of a hub-and-spoke network. 
• I also started a social media practice, a monthly email digest, and an executive communications strategy and production process. 

I didn’t count all of the blog posts that I published here (including my 1000th!), which I’m absolutely delighted by. There were also some really important personal practices I shipped, including a meditation practice and journaling. I got to do a fair amount of travelling, including my honeymoon with my partner which was really special to me. 

Still, I get the nagging feeling some things are missing. I’ll add any I missed as they come boomeranging back to my mind. 

Happy new year! 

You can find a list of some of my earlier projects here:

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