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How to make your holiday issues shine

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Hi there,
As we approach the end of 2021, we’re officially entering newsletter roundup season. If you’re looking for inspiration to fill your end-of-year issues, you’ve come to the right place.
Below, I’ll lay out some different formatting options, plus some great examples. Let’s dive in.
Why send an end-of-year issue?
Firstly, let’s take a look at why you might want to change up your regular format to send an end-of-year special:
  • You can pick a format that can be prepared in advance, then take some time off. I mentioned how important taking a writing break can be in last week’s issue — and I’ll be taking my own advice in coming weeks with two special issues of The Week in Newsletters that I’m working on right now.
  • Even if you’re not taking a break, switching up your content or structure can lead to helpful realizations. Your readers might really enjoy an element of your holiday issue, and you could choose to continue it into the New Year.
  • Looking back over the year gone by can be a great opportunity to zoom out and think more broadly about your subject. What trends can you see? Can you incorporate any of them into next year’s strategy?
  • You may wish to use this moment to engage with other writers, or to join a conversation surrounding your subject on social media. Maybe send a Tweet asking people to add their predictions for the next year. You’ll get a broader perspective on what’s to come, plus the added bonus of engaging with your newsletter community.
Now we’ve looked at why you might send an end-of-year issue, I’ve got some great examples for you.
Check out the next section for inspiration. 👇
Types of holiday specials
Year-end roundup
This is a format you’ve likely seen in your inbox before — think “What 2021 taught us about [insert your topic here]”. It’s versatile, it works just as well for independent newsletters as it does for organizations, and can fit nicely with whatever you want to write about.
2020 was a particularly fertile crop of year-end roundups as our collective pandemic experience made strangers’ day-to-day lives more relatable than ever before.
One of my favorites was the December 30th issue of Tedium by Ernie Smith — a long read that dissected the year in his typical essay-format style.
I enjoyed this issue preview on the Tedium website because it appeals to our shared experience of being utterly baffled by the year that just passed:
If you tend to write short rather than long, you could go for a scannable issue, broken up into a list.
For example, Ann Friedman’s compiles a yearly “12 days of GIFmas” for the Ann Friedman Weekly, where she curates key events through the year and presents them in the form of a GIF (plus a link for context, sometimes). Honestly, it’s a joy every year and a reason to subscribe to her newsletter all by itself:
But Ann broke that tradition in 2020 with a stunning year-end issue compiled from survey responses from her readers on how they spent the first year of the pandemic. It’s tender, revealing, joyful, sad — and an excellent example of how a community can lift a newsletter.
A predictions issue
You could use the end of the year as a chance to look ahead at what might be in the works for your industry or area of interest in 2022.
A great example of this is the Nieman Lab, which puts together an annual predictions issue for the year ahead in journalism, tapping the great minds of journalism and media. The issue is comprised of key quotes and points from industry experts, and readers can click through to read the predictions in full:
The Week in Newsletters did predictions issues for 2020 and 2021 — the feedback we got was fantastic, and we’ll be doing something similar in the weeks ahead.
A promotional issue/membership drive
Promotion is absolutely vital as an independent writer. I really liked freelance journalist Jewel Wicker’s 2020 year-in-review for her newsletter As Told To, in which she included links to her top-five bylines of the year:
It’s a smart way to drive traffic back to your most popular content (you could do the same with newsletter issues, for example).
On another note, tech writer Martin SFP Bryant uses the holidays as a way to promote paid subscriptions to his Tech Revolution newsletter. For the last few years, issues over the holiday period have all been sent to paying members only:
Martin uses the introduction of his last free issue of the year to encourage free subscribers to convert:
Wrapping up
If you do intend to send issues of your newsletter over the holiday period (and I’ll take this chance again to give you permission to take a break instead), I hope the examples above have given you some inspiration. I’d love to hear about your plans for the weeks ahead — you can find me by hitting reply!
And one last thing — I’ll be working less over the holidays and New Year so I may be slow to get back to you, but I still love reading your messages and will reply when I can.
In the meantime, I wish you a very happy holidays, and I’ll see you soon.
Best,
Anna
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