I’ve reached out to some wonderful creators, both with a well-established crowd of followers and the ones who are only at the beginning of their newsletter journeys. The goal was to learn the secrets of publishing stellar content on a regular basis — all while avoiding creative burnout.
In this article, I’ll share with you my findings, everything I learned from five amazing newsletter writers.
Let’s meet our guests, shall we? (They’ve been nothing but sweet, give them a follow, subscribe to their newsletters as a way to say thank you! The newsletter and Twitter links are included at the end as well 😉)
Here’s Tyler McCall, the creator of Lincoln Hawk Fan Club, a newsletter about “Gossip Girl". Tyler does deep dives into each episode of this iconic show. You can say "hi" to her on Instagram and Twitter. Tyler's posts are just as iconic as the show itself.
Gary Suarez is a legend of music journalism. He describes Cabbages as a “hip-hop newsletter focused on music discovery, with a particular slant towards independent artists and self-released work.” Quality material, every single time! Here’s his Twitter.
Next up is Josh Spiegel, an expert on everything Disney. In his own words, alongside the commentary on The Walt Disney Company, his newsletter That Still, Small Voice includes “the goofy thing [...]: March Madness-style 64-seed brackets all themed to various aspects of Disney.” As per Josh, it’s “the only Disney newsletter that you'll ever need.” And we agree. Catch up with the latest news on his Twitter.
I also had the pleasure to chat with Kayleigh Donaldson. Her newsletter, The Gossip Reading Club, is the place where you can read stellar in-depth pieces on “how our understanding of fame, art, politics, etc, has been widely influenced by celebrity gossip.” “Every issue focuses on a specific [...] interview, a profile, or notable piece of celebrity coverage.” Kayleigh invites “others to join in with their opinions.” You can do it on her Twitter as well!
It was especially exciting for me to talk with Grace Robertson, the creator whose newsletter is an absolute gem for all the football/soccer fans (like me. Go, Chelsea 💙). Grace on Football is “primarily but not exclusively focused on the Premier League. In her newsletter, statistical and tactical analysis are mixed with a bit of a sense of the cultural context of what’s happening.” Such a delight to read for any fan of this beautiful game. Grace is also active on Twitter, no major game or social issue will be left out!
So what did we talk about?
Let’s start with all things frequency and content planning.
The wide range of topics, different cadence, and history of newsletter publications — despite such representation, it was a surprising discovery for me that in the end, the content calendar is not that important for a quality newsletter. As in, if you’re running a personal newsletter on your own. However, a content calendar is everything for teams of writers or businesses.
A content calendar is not a must if you know what you’re writing about.
In Tyler’s case, the newsletter follows the show’s structure. She uses “the episode as a launching pad” since she’s “so familiar with the show”. Gary is in a somewhat similar place, he keeps “a rudimentary content calendar just to keep track of artist interview scheduling and album releases”. And yet, so much is coming out within “hip-hop and rap music in the streaming economy” so there’s no other way but to “be flexible.”
In the same content calendar-less boat is Josh, however, he does have “a long (very long) list of future bracket ideas that eventually drives some of the content.” Kayleigh, like Josh, has a wealth of knowledge about the topic she writes about. For this reason, she keeps “a notebook for all of work ideas, reviews, notes, etc”, where she plans each newsletter. Grace allows the industry to define her creative process. In her own words, she’s been “fortunate in that regard to write about a subject where there’s always something new happening, [...] so there has been more to write about than time allows.”
Even if you don’t have a strict calendar for your content, keeping tabs on possible topics and materials is a must. You need to have material in store. As Gary shared with us, “[a content calendar] helps to bank some content for those weeks where life or work make it impossible to create.” Kayleigh is an adept of preparing materials in advance: “I typically do a lot of issues ahead of time, or at least early drafts of them. Then, a few days before publication, I go over and fine-tune things or offer more heavy rewrites.”
Your future self will be grateful!
And still, content calendar or not, newsletter consistency is something to not be neglected.
All 5 creators agree that consistency is everything. “But so is flexibility,” points out Kayleigh. “It's good to have your lane and you can't restrict yourself to just that. I always want to make myself open to change and suggestions from readers since it's their time I'm hogging with my newsletter.”
It’s an excellent point. You cannot forget that you, indeed, fight for your readers’ time and attention. Josh is very realistic on this: “it's incredibly easy for people to forget your newsletter is out there if you're not regularly reminding them.” Gary agrees: “Even if you're not charging people for access, you're asking for their time and attention. If you can't get at least one thing in people's inboxes every week, you may want to rethink doing a newsletter.” Josh joins this narrative, in his opinion, “your writing may be excellent, but if it's not being delivered frequently enough, you're not likely to lure in a wider audience over time.”
If the weekly schedule is not working for you it’s absolutely okay! Start publishing, the process will help you define your ideal pace.
Grace summed it up perfectly, saying that while “it’s great to surprise [your readers] at times and spice things up,” it's not going to work unless there’s “a baseline reliability.”
Now we know that a calendar is not a must for consistent quality content. Let’s talk about the balance now. The one between quality and quantity.
In the course of these brief chats with creators, it became apparent that cadence provides more for your newsletter than just structure and schedule.
A wisely chosen pace helps you maintain the joy of writing while keeping your subscribers satisfied and entertained.
Tyler suggests remembering your individual style of work, in what conditions you perform the best. Her newsletter stands out as it follows the already existing sequence of the show’s episodes. And yet Tyler is still in the search of her perfect publication cadence: “I consider bumping up to two issues a week, because the series is quite long and I'm eager to get through it, but I also know my writing isn't as strong when I crank out a lot of stuff at once so I'm keeping it to just one a week. I take notes of everything I'm thinking when I watch the episode and I filter it out when writing so it's not just crammed full of throwaway things.” Notice how mindful Tyler is about her strengths and weaknesses as a writer. I can only applaud it.
How do I find this sweet spot between quality and quantity? Gary is just as brutally honest as Tyler: “Trial and error. You have to do the work, writing and self-editing and publishing and so on. The first newsletter I dropped in January of last year doesn't look exactly like the one I sent in January of this year. It's only by committing to it that I learned and adapted to the format.”
Love what you do, work on it carefully. As every newsletter creator, Josh strives to make “not the kind of email you see every day from this or that company that you automatically just delete from your inbox or send to the archive”. To stand out, he makes sure that everything he’s writing is something he works on carefully, “so that whoever's subscribing not only reads it, but wants to read it.”
Remember how Kayleigh said she prepares a lot of issues in advance? Even then, before publishing, she “fine-tunes things” or “offers more heavy rewrites”. Here’s what she says about the quality of her content: “I need that space in-between the work and hitting send to let things settle. Otherwise, I just end up looking at the thing I wrote and immediately deeming it terrible. Sometimes, ideas need a few days to breathe, especially on something so high-low stakes as celebrity culture and gossip.” Another honest answer, I admire this courage and transparency!
Grace reminds us that flexibility is crucial. When asked about maintaining the quality of her newsletter, her response was “I think in that regard it’s important not to get too rigid. [...] There have been times when I’ve felt like I need to get something out I’m not 100% happy with, but for the most part I try to favour quality.”
You’re a human, do not forget it, be forgiving to yourself.
Speaking of being human.
Staying on top of your newsletter game, meticulously proofreading and fact-checking your writing can be and is exhausting.
Consistency is key, yes. It’s also true that skipping issues of your newsletter is normal.
For most creators, newsletters retain a hobby status, stay a side hustle. Just like for Tyler and her full-time writing job, she wanted “[newsletter] to feel fun and not like a chore. I get to watch my favorite show and discuss it with other people who love it too. By pacing myself, I'm able to feel excited about working on my newsletter every week.” As of the day this article is published, Tyler hits a send button weekly. She remains excited and hopeful: “knock on wood! — I haven't skipped a day yet! Fingers crossed I can keep that up.”
The writing process should bring you joy, even if you have to push yourself at times. Here’s Gary talking about his own journey with discovering his perfect workflow: “the Sunday newsletter at one point was enormous, and I realized I was asking too much of the readers and of myself, really.” Another wise piece of advice from Gary: “you need to start with an idea that you think you can reasonably sustain for 52 weeks. Otherwise, you're setting yourself up for burnout.”
Stay realistic and forgiving to yourself. Writing on a regular basis is a tough job. Josh shared with us how burnout is, sadly, a part of the creative process. “It's a speed bump [...], and while it's never pleasant to mount, you pass it by over time (hopefully over very little time) and move onto the next exciting challenge.”
Kayleigh understands what newsletter creators have to come through psychologically. She referred to burnout as “a freelancer’s curse.” Kayleigh’s mindfulness is outstanding. She honestly admitted having “a habit of getting lofty ideas and planning amazing things, only to abandon them before they ever come to fruition.”
Incredibly relatable remarks. There’s a silver lining despite such obstacles. Yes, it may be scary to have your “newsletter out there and being read by hundreds of people.” But it’s important to remember that what you do has value to subscribers which makes it worth continuing with.
I should thank Grace as well for being so open about her own writing process. Here’s what she said: “I try to hit two articles a week and I’d be the first to admit I’ve been slacking recently, though that tends to happen in the build up to bigger projects for subscribers, so hopefully they feel as though they’ll get their money’s worth in the long run.” With such a tight and demanding schedule she remains optimistic: “It’s entirely possible I’ll feel differently in a year, but I think I’ve managed to avoid [burnout] so far.” Stepping out from what she’s been working on helps her stay energetic and inspired. “I know it’s not ideal if you’re on Twitter all the time, but it’s a big internet. You’ll find something else to read.”
Even well-established creators have their struggles! It’s perfectly human to get tired, feel the lack of inspiration, and be riddled with self-doubt.
I’ll leave you with words of reassurance from Gary: “[...] unless you're charging a high subscription rate, your readers will be forgiving of your growing pains and stick around for the ride.”
Do you feel encouraged to finally start that newsletter you’ve been thinking about?
To wrap up this article, we have some tips from our wonderful guests on how to stay consistent when you just start.
When possible, do not leave writing until the last minute. I myself am guilty of this. Tyler plans her week, “finding space to try and get ahead of myself has been helpful.” This saves her from panicking on a Sunday night “about not having the issue for Monday done.”
Gary, too, supports the idea of planning your week ahead. “Give yourself the breathing room to go back and edit before deploying. There are going to be times where that's not feasible, but set out for an unchaotic norm so that the chaotic weeks are exceptions.”
Basically, “don’t cram.” This applies to life in general.
Grace supports the notion of taking it easier and finding the rhythm on the go. “Just don’t stress yourself out too much about going in hard. If you’re militant about publishing all the time, you’re probably just gonna crash and give up on it when it gets too hard.” No newsletter worth straining your mental and physical wellbeing.
However, if you are looking for a more structured and disciplined approach, Josh can motivate you like no other! “You almost have to force yourself to write every day. [...] If I stopped posting, no one would be to blame except me. If you want to start up a newsletter, you have to prepare yourself for the reality that it's a long haul. No one's holding you back from writing it except you.” Know you can do it. And do it.
There’s no universal solution. It takes time but the journey of self-discovery will pay off, “so don't be afraid to find your own pace and style of work.” It’s Kayleigh and her supportive piece of advice. You are not alone. “Don't be afraid to ask for help from other writers or even your readers. There's a refreshingly personal aspect to newsletters that allows for that quality.”
If you’re reading this article, then know that you are good enough and ready for writing.
Don’t forget to enjoy the ride!
Show these creators some love and appreciation, follow them! Without these talented writers, this article would not have been possible.
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