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Three quick tips for sending weekly newsletters

Kristian Freeman
Kristian Freeman

Bytesized Weekly, my weekly newsletter for software developers, is just about to hit issue #30. It's been a strange year, so I haven't quite reached a 100% success rate on sending every week, but I have learned a lot about sending weekly newsletters and how to stay consistent.

In this blog post, I'll cover a few tips that I've discovered that make it really easy to send a weekly newsletter.

Note that while my newsletter is focused on sending a few links that I find interesting every week, not all of these tips are necessarily related to that style of newsletter, so you can take them and apply them to whatever you're publishing.

Tip #1: Solicit (and process) feedback

One of the most effective things you can do to generate new content, and make sure that what you are sending is valuable, is to solicit feedback.

This can be really simple: set your newsletter's "From" address to a real email, and check it!

Every issue of Bytesized Weekly is sent from my real email, so every week, I receive a few emails in response to whatever I just sent out. Often, that's in the form of "thanks, this is cool!", which is great (though not totally actionable) feedback.

Other times, I get really important information: last week I discovered via a subscriber that emails from Bytesized Weekly were going into their spam folder!

That sort of feedback is super critical and if you don't have a simple way to receive info like that (for instance, if you point people to a multi-step contact form on your website), many subscribers simply won't take the time to fill it out, because it's too much work.

For newsletters where you share cool links like mine, this is also a goldmine of potential content. Simply ask people at the end of the email if they've seen anything cool recently!

A lot of my favorite instances of links in my weekly newsletter have been really nascent projects developed by subscribers of my list, that I've been able to share with my list.

In addition, this style of generating content for your emails can also give them a sense of continuity – if I share a resource about teaching developers design skills, a subscriber may reach out and say "Here's another great resource on that topic", and then in the following week, I can share that resource as a continuation of what I shared the week before. It's a great loop to get into, because it helps your subscribers feel connected to the content, and it also makes your job a lot easier.

Tip #2: Bookmarks are your friend

It's Monday night, and your weekly newsletter is due to be sent tomorrow morning, bright and early so your subscribers can read it with their morning coffee. The bad news: you have nothing planned. What do you write about?

This was a shockingly common occurrence for me as I started writing my weekly newsletter.

While there were weeks with a clear theme or an idea that I had been kicking around all week, many times I found myself staring at ConvertKit's blank editor page on a Monday night with no idea what to talk about.

This tip may be most applicable to link-style newsletters like mine, but it can be an extremely powerful tool to just bookmark things you find interesting throughout the week.

If you're like me, you're reading a ton of articles every week and by the night you're writing your newsletter, you've probably forgotten many of them. Keeping bookmarks of things you know will be interesting for the newsletter throughout the week makes it super easy to pull up a list of items to choose from when it's time to write, and it saves you from the dread of staring at a blank screen with no idea how to start.

Even if you aren't writing a link-style newsletter, this approach can be really useful. There's a great chance that whatever you've been reading this week has influenced what you're thinking about, and keeping a list of the articles you've been reading could make for a really effective newsletter issue where you tie those articles together and add your own spin.

For most people, this can be as simple as using your browser's bookmark feature, but if you want to bookmark between devices or tag your bookmarks by concept, Pocket is a great free option, although it's more oriented for reading bookmarks, whereas Pinboard is a very cool (albeit paid) option focused primarily on bookmarking.

Tip #3: Share your greatest hits

For most Mailing List Hackers out there, the sign of a successful newsletter is one where people are opening and reading your emails, but also that your list itself is growing.

For Bytesized Weekly, I started my ConvertKit account by importing around 700 "warm" subscribers to my list, and recently, hit 4000 subscribers. This means that at best, roughly 20% of my list has seen any of my previous content or any previous newsletter.

If you're creating your own content to show to your newsletter, this presents an awesome opportunity to recycle content, by showing new subscribers (and reminding older subscribers about) the "greatest hits" of what you've made in the past.

These “back by popular demand” articles are valuable to build credibility as well. You’re not just showing up with an email or two that you’ve written in the last week: you have a treasure trove of content to share, and you care enough to catch people up and make sure you’re consistently providing value.

For my projects, this means that a YouTube video or a series of tutorials that I wrote a year ago, as long as it's still relevant, is a perfect thing to show in a new newsletter.

Don't overdo it – I'd caution against an entire newsletter with year-old content, but an item a week is totally reasonable and to many people in your list, will feel entirely new.

With my remote software conferences Byteconf, I pick a conference talk from the past few years of events and share it as one of the last items in the newsletter. It's often not the most-clicked link in the newsletter, but it also serves as a reminder of the longevity of the project and gives some credibility that if someone is just joining, they're signing on to a fairly long-lived project (aka “your treasure trove”) and will continue to get value from it in the future.


These are just a few tips to make it easier to produce a weekly newsletter – what tips do you have? Join us in our Mailing List Hackers community and let us know how long you've been writing your newsletter, or if you're just thinking of starting one, share it with us so we can subscribe and cheer you on!

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Kristian Freeman

I'm a programmer and writer — I also founded Mailing List Hackers! I love to teach, write, and make stuff online.