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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:
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:
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.