How to publish a weekly newsletter in 4 hours or less (Building a Second Brain case study)

A quick conversation with other newsletter creators reveal that most of them spend about 5-8 hours on their weekly newsletters each week.

Thanks to Building a Second Brain, I’ve cut that time down to 4 pain-free hours maximum.

Here are a couple of notes on my process before we get into the walkthoughs:

I like to split each part up into different days. I tend to start my Monday newsletter on Friday mornings, Saturday mornings, or Sunday mornings. Specifically, curating and outlining are ideally done on Friday morning, and the actual writing done on Saturday morning or Monday morning.

My weekly newsletter is the culmination of my weekly review. I bake the curation process of my newsletter into my weekly review checklist. It’s a way for me to regularly practice going through the Building a Second Brain process:

  • When I curate, I progressively summarize the resources I might want to share.
  • When I write about the resources, I get into Level 4 and 5 of progressive summarization — sharing my thoughts and remixing them into my newsletter.
  • When I work on my newsletter, I practice slow-cooking, project planning, and project completion every week. I accelerate the feedback loop of my second brain system. I achieve unconscious competence in using my second brain faster.


Finally, like my previous Building a Second Brain post,the actual walkthroughs are in the videos. This article will just fill in the details.

Part 1: Headache-Free Curation (~30 min. - 1.5 hours)

Evernote is where 90% of my newsletter curation happens because that’s where most of my resources are stored. But some weeks, I capture tools or action items in my Things 3 project for that newsletter. So I make sure to check that, too.

A step that I didn’t show in the video is what I do after I put my notes outline together. Before I add them to the Markdown template, I progressively summarize notes I want to share. I read through each note in my outline, bold items that catch my eye, and highlight items that are already bolded to emphasize them even more.

By doing this step, I only progressively summarize the notes that I already find interesting. I don’t waste any time on notes that I wouldn’t even consider adding to my newsletter.

Instead of moving notes over to the newsletter project folder, I add a table of contents note. This way, the resource notes stay in their topical containers, and are more easily searchable and reusable for future projects.

Finally, when I paste the Markdown outline to Ulysses, I don’t stop the session there. I like to fix the links and make sure they’re all in Markdown formatting. Maybe write the first paragraph or a few points under each recommendation. This greases the wheels and makes it easier for me to just write in the next session.

Part 2: Pain-Free Writing and Editing (~2 hours)

It’s all downhill after the thorough setup in the first section. All the logic — my resources, links, quotes, and recommendations — are ready to be turned into language.

(Tip: I type “TK” for parts I need to fill in with photos or a link. Many writers and bloggers use “TK” to mark up document edits because it’s rare to find those two letters together. On ConvertKit, I do a search for all the “TK” bits in my writing, which usually mean to add a link or drag in a photo from Ulysses. Ironically “ConvertKit”, the name of my email service provider, is one of the few words that has it.)

I really like writing in Ulysses because it removes many of the barriers between writing and publishing:

  • Writing in Markdown means my fingers don’t have to leave my keyboard.
  • Copying the Markdown as HTML (without annoying spanstyles!) means I don’t need a render window. All my formatting appears in ConvertKit exactly how I visualized it in Ulysses.

After editing, I’m usually good to go and I hit “Publish”.

In-Depth: How to Edit Quickly (but Suprisingly Thoroughly)

This is how I’ve edited every academic essay, research paper, article, newsletter, and email for the past 5-8 years. Hat tip to Cal Newport.

  1. Read for arguments. I read through my writing and try to spot any janky transitions and vague language. I do this on Ulysses because this pass creates the most changes in the document. After this pass, I export my Markdown to HTML and paste it into ConvertKit’s HTML editor.
  2. Read it through, out loud. Pasting clean HTML means I don’t have to worry about formatting the email in ConvertKit. I can focus on editing my work in a fresh environment, increasing the chance I’ll spot typos. And yes, I silently mouth each word when I do this edit — this really tests for rhythm and flow, regardless of grammatical correctness.
  3. Just read. I send myself a test email on desktop, mobile, or tablet and I read to experience my work the way my reader would. If I spot any mistakes, I make a note and change after I finish reading.

Even with my 500 - 1,000 word emails, this editing process takes 10 - 30 minutes and catches 99% of mistakes.

Part 3: How to deal with recurring projects in Building a Second Brain and P.A.R.A.

TL;DW I have an Area for each specific recurring project. I create a new project each occurrence of that recurring project.This was probably the biggest undocumented BASB/PARA problem that I’m proud to solve.

I don’t run through a comprehensive project completion checklist yet. I’m working on it. For now, the only thing I do after a project is start the next project as soon as I finish a one to maintain momentum (a.k.a. daisy-chaining or chainsmoking. H/T Austin Kleon).

Finally, I want to emphasize that the Evernote project for each newsletter only gets created after the Things 3 project is created. This rule respects my Things dashboard as my master projects list where all the other software’s project lists are synced to.

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