On February 14, 2022, I started playing a game. I could win by writing a blog post every day for 100 days. 

Before the game, writing had felt like a chore on good days and torturous on bad days. I struggled to find my way out of the mindset of “content creation.” I started the game of writing every day to change this. Since there was no way I could possibly publish something good every day, maybe I could say more nice things to myself and learn to be satisfied with publishing something. I could learn to allow the good work to come out, and not to force it. I wanted to practice the craft of writing, and learn to love the process.

As it turns out, the game was more fun and rewarding than I could have imagined. I didn’t want to stop—so I didn’t. 1,000 days later, I’m still playing. I’ll explain how the game works—but before I do that, I need to tell you a story to help frame it:

The most fun game in Japan

It’s the year 2000. Nintendo’s game sales had completely fallen off, and nobody except game designer Shigeru Miyamoto seemed to understand why. In Nintendo Magic, Osamu Inoue writes:

On the train, [Miyamoto] saw kids sending text messages to each other constantly. They were clearly enjoying themselves. As he watched them tap out rapid-fire missives on their phones’ keypads as though they were playing a game, he felt a terrible jealousy.

Later he would sarcastically say to some of Nintendo’s software team, “Sending text messages is way more fun for them than any game we make. If we made a game where you have to type a certain message as fast as possible and competed nationwide, that’d probably be the most fun game in Japan.”

Framing text messaging as a game is equal parts fascinating and unusual. It’s not the same as a board game like Catan, which ends the moment somebody scores 10 points and wins. Or a game of basketball, which ends with whoever has the higher score after regulation time (or over time) claiming victory. Text messaging isn’t even like a puzzle, which you win when you complete it. These types of games are called finite games, where the goal is to win and stop playing. 

But text messaging is different. You can’t really claim victory and stop playing through a text message, anymore than you can “win” a conversation that way. In this sense, text messaging is much more like an infinite game: one where you play in order to keep playing.

In other words, one way to see it is you win at text messaging when you get to continue text messaging someone. You win when the recipient responds and you get another chance to keep playing.

You play by deepening the relationship in some way, whether that is through more texts, a video call or in-person meet up. You play when you try to make a loved one feel good. You play when you send an important message. You play when you tell a joke. 

Blogging as an infinite game

If Miyamoto can frame text messaging as a game, I want to frame writing on a blog every day as a similar, infinite, game too. There are some important reasons for this:

• Make blogging fun again: Social media is much faster, wider-reaching, and has gamified elements that make it more dopaminergic than blogging. This is mainly why it has survived more widely than blogging. Blogging every day has its own fun though—it’s quieter, rewards you for developing your authentic voice (not engagement farming), and when you publish a post you feel energized (and not drained like social media).
• Separate blogging from self-promotion: You can flaunt some cool results from blogging, of course—but at the end of the day, that’s not the point. The second getting results becomes the point, you’re no longer playing the game of blogging—you are playing the game of self-promotion, which is a completely different game. The second you change, edit, or compromise your voice in a bid to increase reach or engagement, you’re also playing self-promotion.
• Encourage more people to join the game: When my friend Michael started writing at his blog for 100 days, I found myself checking his blog every day, excited to read his work and possibly to respond to it as well. It was very energizing for my practice. I really hope more people write every day—because it will give me energy to play the game of blogging for longer as well. Perhaps more people would try this if they had a set of rules that worked for them.

Winning is simple: you only win when you keep writing at your blog. When you don’t run out of things to say. When you notice something interesting, fresh, and new every day. When you put down your disguises and need for engagement, and express yourself in your voice. When you’re writing for the hell of it, and not to achieve some sort of external result.

Here are the rules that I have intuitively developed to write at this blog every day for 1,000 days:

Rule 1: Write and publish one post at your blog every day. (Loophole: If you miss a day, write two the next day. Make an earnest effort to catch up, and don’t beat yourself up if you fall further behind. Avoid falling past a backlog of 10 posts. As long as you keep going, and eventually catch up, you’re still playing.)

Rule 2: Every narrative you tell yourself gives you more energy to keep writing posts—not to drain that energy away. (e.g., If you tell yourself the statement, “My blog needs to make more money,” and you feel that energizes you, then by all means. But if that statement drains you of energy, then try a different statement.)

Rule 3: Each post is so energizing to write that you would have written it even if nobody else saw it.

Rule 4: Each post must contain five original sentences that you typed by hand minimum. Anything more is nice, but not necessary.

Rule 5: Every time you publish or schedule a new post, you win.

Rule 6: Every post must have 0% AI generated or edited text.

Rule 7: Every time a positive outcome happens (e.g., a post hits the front page of Hacker News, gets picked up by a newsletter, or gains momentum at another platform), you file it away in a happiness folder.

I hope these rules can be a starting point for you to develop your own rules as you consider starting your own game of blogging.

What’s next?

Well, I will probably buy myself a glass of champagne to celebrate. And then I will continue to write here, every day. 

Writing at this blog started as, and remains, one of my favorite parts of each day. I do have one gripe: hopefully it gets easier. My ideal time to write is in the mornings, but I have lost count of the nights that I have cradled my head, staring at the laptop screen and struggling through a post. Seth Godin, who is well on his way to writing 10,000 blog posts, has called the first 1,000 posts the most difficult.

This blog has sustained my creative energy through many different life transitions. Professionally, I shifted from working independently on Wonder Shuttle to joining Figma as a content strategist, and then starting a new gig with FGX as its director of marketing. I have moved from Hong Kong, to Toronto, to New York City while writing this. I have gotten married. 

While it certainly has not been easy, showing up to this blog every day has been one of the most rewarding things I’ve ever done for myself. I think you’ll find it can do the same for you. 

If you want to celebrate with me, the best way you can do that is to write a blog post for yourself and starting to play the game.