May 20, 2022

Blogging Streaks & Freaks

Again and again and again

I’ve been writing at least one blog post a week for the last 10 weeks. This idea of streaks is completely inspired by Matt Webb who would totally be on the cover of Blogging Weekly (if such a magazine existed).

Matt Webb’s current streak is 112 weeks so I’m only…checks notes…about 100 weeks behind.

Inspired by Matt’s 15 rules for blogging I thought I’d write up some notes. These aren’t rules, they’re more like provocations…? I think you can blog any way you like. But maybe these could be useful:

1. Keep a drafts folder

If you want to write more blog posts you have to start more blog posts. I have a drafts folder with over 50 blog posts in various stages of completion. Some of these are only a few sentences, or only a headline. This post about things I failed to get done at Google has sat in my drafts folder since 2019, waiting for me to have enough courage and separation from Google to post it without having a nervous breakdown.

I’m always surprised how often I have the right headline and the wrong post, or the right post with the wrong headline. Then when inspiration strikes I have some raw materials I can remix, cut up and dust off. Having posts in drafts is like having dry kindling, waiting to be lit up by the right spark.

2. Inquiry over insight

Personally, I much prefer to read blog posts that open up a line of thinking rather than close it down. Trying to “solve” things or provide the “definitive” anything is a recipe for bland content. If you’re writing, consider opening up the questions - I like to write blog posts where the reader comes away with more questions than they started with!

A good recipe for this is to share your personal expertise or perspective, resisting the urge to suggest anyone else should follow you. This might seem unnatural for people who are trained to project confidence. But these personal stories and personal perspectives are, I think, part of what makes independent writing so powerful - don’t tell people what to do, just show them how you think.

3. The unit of measurement is the conversation

Analytics. Ugh. The only good measurement of blogging is how many conversations did you have off the back of it? Sometimes a blog post with only a few hundred page views will trigger lengthy twitter DM conversations, or a podcast appearance, or a coffee meeting. This is my north star for blog posts - will it trigger a conversation?

Related:

4. Write for an audience of one

If you’re stuck - write a blog post that you want a specific person to read. This is a writing tip from Steinbeck:

Forget your generalized audience. In the first place, the nameless, faceless audience will scare you to death and in the second place, unlike the theater, it doesn’t exist. In writing, your audience is one single reader. I have found that sometimes it helps to pick out one person—a real person you know, or an imagined person and write to that one.

If you want someone to find a post interesting, write it for that one person.

An obvious extension of this is that you should always have at least one person that you’re excited to send your latest post to. If there isn’t a single, specific person that you’re excited to email or text your post to, then chances are no one will find it interesting…

5. Make it distinctive

In a sea of generic, bland content you need to stand out. The best way to do this is to lean into your quirks, your weirdness, your strangeness, your passions. In short, don’t hide the blogpunk. Focus on writing in your own tone and voice - not in someone else’s. If you like doodling in your notebook then include some photos of your notebook! If you like quoting poetry, then quote poetry! Make it yours first and foremost.

I wrote more about this idea in my post small-b blogging.


I’m not sure how long this streak will last. But I’m enjoying it so far.

Anyway, if you’re blogging using Jekyll/Github Pages then you can copy the weekly streak code here. It’s my own code, not well documented and likely has bugs. You have been warned. But maybe it’ll encourage you to blog a little more and that, I think, is a good thing.


This blog is written by Tom Critchlow, an independent strategy consultant living and working in Brooklyn, NY. If you like what you read please leave a comment below in disqus or sign up for my Tinyletter.