Brian Gilham

Engineering leader, husband, and father

newsletter

Growing Without Schooling →

What if school, in fact, isn’t the best place for your kids to learn? What if you didn’t try to replicate school at home? What if you had the opportunity, now, to try something else? What if we saw this time as a radical opportunity to let our kids learn and explore their interests unfettered by the demands of the classroom? What would happen if you stopped worrying about teaching them and gave your kids the time, space, and materials to lead their own learning? What would happen if you let them in on your working life, let them see you working, involved them more deeply in the work of keeping up a house and a home life?

We’re only three (almost four!) weeks into raising The Kid, but I find myself thinking about this stuff a lot.


If you’ve been following me for a few years, you might remember when I wrote the Monday Mailer — an email newsletter about productivity, side projects, and feelings. I’m really proud of some of those articles. Some of them make me cringe. Regardless, you can now find the archives here.


Monday Mailer Survey 2016

Two weeks ago, I wrote to the Monday Mailer and asked if my readers would do me a favour and fill out a quick survey. People spend so much time and energy trying to figure out what their audience wants — I figured I’d just ask them. 130 people were kind enough to take 6 minutes (on average!) out of their busy schedules and fill it out. Their answers will help me create great content for the newsletter & podcast in the year to come.

Two weeks ago, I wrote to the Monday Mailer and asked if my readers would do me a favour and fill out a quick survey. People spend so much time and energy trying to figure out what their audience wants — I figured I’d just ask them. 130 people were kind enough to take 6 minutes (on average!) out of their busy schedules and fill it out. Their answers will help me create great content for the newsletter & podcast in the year to come.

I thought it would be interesting to share some of the results.

Job Titles

84% of respondents identified as a software developer. Of those who didn’t, the most popular job titles were variations on:

  • Product Manager
  • Student
  • Teacher
  • Writer
  • Soldier

Side Projects

68% are working on a side project of some kind, with 58% planning to monetize it. 8% of those who responded have already monetized a side project.

When I asked the other 32% what was holding them back from working on a side project, they said:

  • A lack of time/too busy
  • Not having any ideas
  • No motivation
  • Feeling burnt out
  • Having trouble deciding what to work on

Challenges

Asked what the biggest challenge they were facing in their work was, most people said:

  • Time management/balancing goals & timelines
  • Maintaining motivation
  • Producing good work consistently
  • Staying focused
  • Suffering from imposter syndrome

Learning

Most respondents want to learn more about:

  • Marketing & building an audience
  • Team management & leadership
  • Monetizing their work
  • Learning design skills
  • Improving their time management skills

Elsewhere

When asked about other sites, authors, and podcasts they liked, the most popular answers were:


How I Write & Publish a Weekly Newsletter

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. Planning I publish my newsletter every Monday, and the occasional article during the rest of the week.

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.

Planning

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.

Writing

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.

Publishing

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.

Interacting

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.

Fin

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.