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How I Write & Publish a Weekly Newsletter

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I often receive questions about how I run the Monday Mailer, my weekly newsletter about shipping side projects, productivity, and doing your best work. Readers ask what my writing process is like, and which software tools I use. While I firmly believe tools aren’t all that important — you can make something great, no matter the means— I thought I’d write some of it up for anyone interested.


I publish my newsletter every Monday, and the occasional article during the rest of the week. I also contribute guest posts to other sites, from time to time. I manage all of my writing tasks through Trello. My writing board has a lot of lists on it — 17 in total. They cover everything from the latest newsletter drafts, to guest posts I’m writing, to tracking where I’m publishing & promoting my work. Here’s a quick rundown:

  • Ideas: Whenever I think of something that might make for a good article, I throw it in here. I try not to edit these thoughts too early — if it’s rattling around in my brain, it goes on the list. There’s somewhere in the neighborhood of 60 cards, so far.
  • On Deck: Cards from the “Ideas” list I’m hoping to work on next.
  • Process: Lists that cover every step in my writing & editing process: Outline, 1st Draft, 2nd Draft, 3rd Draft, and Edited.
  • Published: Lists for every place I regularly post my articles: Mailing List, Medium, and LinkedIn.
  • Promoted: Lists for every site I usually use for promoting my work: Hacker News, Designer News, Reddit, and more.
  • Pitched: A single list for keeping track of which publications I’ve submitted to, along with the article and current status.

Phew! My Trello board is probably getting a bit out of hand. But I have so much going on every week; I need an external brain to keep everything organized. Okay, let’s dive into my writing process.


Like many writers, I take an iterative approach. Each round builds on the last. Here’s what it looks like, roughly:

  1. Fire up Ulysses and write a quick and dirty outline. I spew my thoughts onto the page. Every little thought that pops into my head gets written down. I don’t edit or change anything at this stage — it’s all about getting my brain warmed up. If there’s something I need to research, I jot it down as well. Then, I walk away for a while.
  2. Come back, throw the outline on the left side of my screen, and open a new document on the right. I start by expanding on the bullet points in the outline. Again, I’m not too worried about details at this point. I write until I have something mostly resembling sentences and paragraphs. Then, I walk away for a bit.
  3. Put the last draft on the left side of the screen, and a new document on the right. Noticing a pattern, yet? Now it’s time for the real work. On this pass, I work on refining my ideas. I ask myself a few questions: Are things coming across clearly? Am I writing in a way that feels authentic to my personality? Are there any obvious problems? I fix anything I find and then — you guessed it — walk away for a bit.
  4. For this last pass, I run the article through Grammarly. I shell out for the Premium plan every month. It isn’t perfect, but it usually catches a few things I missed in the last draft. Worth every penny, considering the amount of writing I do each month.

I try to dedicate a couple hours to writing every morning. Some articles take a few days — or weeks — to complete; others I can knock off in a few hours. Doing a little bit every day means I always have something I can publish. It also means I’m sometimes a week or two ahead of schedule, which is useful for those moments life throws a curveball my way.


The Monday Mailer has 1,168 subscribers as of this writing. I use Mailchimp’s Send Time Optimization tool to send new articles at an ideal time for the majority of my readers. It usually lands somewhere between 9–10am EST.

After I schedule the week’s newsletter, I add the article to my blog. I used to enjoy fiddling around with hosting my website, but I use Squarespace and enjoy the simplicity it offers. Again, worth every penny. I schedule the blog post to publish two weeks after it goes out to the mailing list. I do the same for the Medium version.

Squarespace automatically tweets a link to the post, once it’s live.

A few people have suggested LinkedIn as a good place to share new articles, so I’ve been giving that a try, as well.


My favorite social network is my mailing list. I set time aside all week to respond to emails from my readers. I’m lucky — they’re never short on feedback and suggestions.

Since the public version of the article is scheduled ahead of time, I can mostly forget about it until it goes live. Once it does, I spend a good chunk of time monitoring the comments, as well as social media, for comments and reaction. I make sure to thank everyone who shares my work. Everyone I can find, at least.


That’s it! It’s a relatively simple process. But it’s one I can repeat consistently, week over week. And that’s the most important part.