One Newsletter Mistake I Wish I Could Take Back

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Everyone who writes newsletters makes mistakes. We’ve all sent the wrong email to the wrong list. We’ve all had to send an apology note to readers. We’ve all used a subject line we later regretted, or forgotten to swap out the placeholder text in an email. (Nothing like thousands of readers waking up to “REMEMBER TO INSERT CLEVER SUBJECT LINE HERE” in their inbox.) 

On the internet, there’s an edit button for pretty much everything except newsletters. That typo, that broken link, that missing image — there’s no way to take it back once you’ve hit send. 

We’ve also all made mistakes when it comes to strategy or content. We’ve chased the wrong metrics, the wrong audiences, the wrong tactics. Work in the newsletter space long enough, and you’ll try more than a few things you wish you hadn’t. (Which is, to be clear, a good thing! It’s better than not trying.)

It can hit hard to realize you’ve made a mistake until you remember — it truly does happen to everyone. So we reached out to a few of our favorite newsletter writers and operators to ask them: What’s one newsletter mistake you wish you could take back? Here’s what they told us.

Anne-Kathrin Gerstlauer
Writer, TextHacks

A mistake I’d reconsider is my paid system. I’m like, “Now that I have 100 subscribers, I need to write an issue for them each week. But does it really make sense? Should I have started the paid? Should I have asked them more specifically what they want from it?” So that is something I’m struggling with. I believed the people who said, “It’s so easy to get paid subscribers; you will get 5%.” And I did not. 

People love my newsletter, so I don’t think it’s just me. I feel like it’s because I gave away everything for free at the beginning and told people, “It’s going to be for free.” The expectations on this newsletter were so high that it made it much harder to ask for money later. 

I should have asked for money from the beginning or not at all. When I started it for free and told everybody it’s free, it was really hard later on to be like, “Now give me some money.”

Asha Dornfest
Writer, Parent of Adults

Before launching paid subscriptions, I’d put more thought into answering this question: What am I asking readers to pay for?

I always knew my newsletter would include a paid option; I wanted to be compensated for my work. But I didn’t think through my paid offering well enough to explain to readers why they should upgrade, or even fully understand it myself. Am I asking them primarily to pay for a product: additional content, access or features? Or am I asking them to pay as a way to invest in my work or show support, as with a tip or contribution? 

Had I been clearer on this in the beginning, I would have written more freely and produced better-quality work. As it happened, I flailed when talking about money (awkward) and felt ashamed for overpromising and underdelivering (unprofessional). 

Lesson learned! I’ve since clarified my paid offering, unleashing a burst of creativity and enthusiasm and more confident invitations to upgrade.

Bill Emkow
Growth Strategy Director, Bridge Michigan

The one newsletter mistake I’d take back is relying on content-to-capture Meta lead gen ads for so long. These looked like news posts — headline, image, teaser — but required users to subscribe before getting the story link. Viral stories brought super-cheap signups.

That approach grew our list from 23,000 to 137,000 over four years, leading to $1 million in annual reader revenue. But many sign-ups weren’t engaged. Engaged readers donate. Last year, we removed 32,000 inactive emails. These ads worked, but inefficiently. In 2025, we shifted to direct ads that pitch the value of our newsletters. We put more thought into the ad creative and pitch; surprisingly, those ads are cheaper than content-to-capture ads. 

Now we’re gaining readers compelled by the newsletter ad, not just a story. A new newsletter launched in April 2025 using this approach has already doubled in size, with a 70% open rate and stronger engagement than any we’ve published.

Cara Goodwin
Writer, Parenting Translator

A mistake I made early on is covering topics that were too niche in my newsletters. I think it’s helpful to think about what would be interesting to the largest percentage of your readers when choosing topics. 

Dan Oshinsky
Consultant, Inbox Collective

Once, at the New Yorker, I was finishing a newsletter on a Friday afternoon before a long holiday weekend, and I accidentally typed in it’s instead of its. The copy editors caught the error, but I forgot to fix the typo before scheduling.

Worse: The error came in a paragraph that was originally written by a senior editor of the magazine.

When I got back to the office after the holiday, we had dozens of emails from readers, most of whom said, with no exaggeration, that they weren’t sure if they could trust a newsroom that could make such a mistake. Many threatened to cancel their subscription. I was at the New Yorker through a few controversial moments, but I never personally saw our audience as angry and upset as they were after my typo.

It was a small mistake, but for some of our readers, it was a significant one. We decided not to send a correction out to the full list — plenty of readers missed the mistake or never opened the email, and it felt odd to call attention to a typo — but I did work with our team to craft an apology email, and sent it to every reader who’d written back.

Minor email mistakes like this happen all the time. Some require a big apology email, and some require smaller steps. (But remember: “Its” is the possessive one!)

Devika Bhushan
Writer, Ask Dr. Devika B.

Never be afraid to experiment and to change things up as circumstances evolve. 

In my case, I simultaneously committed to writing a regular health and well-being newsletter, launching a mental health podcast and YouTube channel, and to building a public health and mental health consulting business. I suddenly found myself being pulled in a few directions.

I quickly realized that good newsletter writing has to be fueled by imagination, energy, and passion — and that fanning these flames requires time and energy. 

Though I had initially started writing the newsletter weekly, I recognized that a weekly release wasn’t going to be successful for me in an ongoing way. I started to experiment with different cadences, lengths, and columns ranging from mental illness journeys to reader Q&As to deep dives to behavioral nudges that built on themselves week after week on topics like screen time and sleep, to photos from my time spent nomadically living in many countries, to find my groove. 

Crucially, I took breaks when my non-newsletter work picked up, and by doing this, I was able to relish the time I did spend writing. I realized that my community was with me through the seasons of life, and that I could show up as I was to the newsletter. And though the recovering perfectionist in me didn’t always agree, this meant that I could write about the topics that moved me in ways that I found fulfilling when I found myself able to do it, and I found myself understanding that this is and would be enough.

So here’s the mistake I made that I have since happily unmade: Never hold yourself to an unrealistic external set of standards about what newsletter writing has to look like, and in allowing the process and outcomes to be flexible, you will be more likely to find your joy and energy in it.

Francis Zierer
Writer, Creator Spotlight

I’ve been writing Creator Spotlight for one year at this point, and I wish I’d inserted more of myself into it earlier. It’s an interview-based newsletter; I research a creator, record an hour-long podcast with them, then write a profile piece based on the research and conversation. 

For much of the first year, to keep the focus on the guests, I tried to maintain a degree of formality in the newsletter, a neutral-observer tone, like using “we” instead of “I” to refer to myself in the piece. Later in the year, I wrote a couple of original essays not tied to any specific interview guest. These received some of the best responses of any issues all year in terms of replies to the email and shares on social media. 

Newsletters are personal! People want a singular point of view! I was too cautious, probably afraid of criticism or of being wrong. But it’s good to take these risks, to put yourself out there, to open yourself up to being wrong. It’s more engaging and creates a stronger connection with the audience. This is a core part of what it means to be a “creator”; your appeal hinges significantly on your own personality and specific point of view. 

Ignacio Pereyra
Writer, Recalculating

One mistake I wish I could take back? Waiting too long to start publishing. A full year passed after receiving an ICFJ grant before I finally launched. I spent too much time overthinking platforms, growth strategies, and technical details instead of focusing on the most important thing: creating and sharing valuable writing. I kept telling myself I needed the perfect setup before launching, but in reality, the best way to learn and improve is by doing.

At some point, I heard the phrase “Start small, but start,” and I now realize how true that is. It’s like riding a bike — you find your balance through action, not theory. You don’t need the perfect platform, the ultimate strategy, the perfect business model or a growth plan. You just need to begin by seeing any potential error as a learning step. Mistakes aren’t failures; they’re part of the learning process.

A newsletter takes shape as you engage with readers, listen to them, and adjust along the way, testing ideas. Refining as you go is far more valuable than waiting for perfection. The sooner you put your work out there, the sooner you can refine it and grow. So if you’re hesitating — don’t. Start now.

Jen A. Miller
Writer, Notes from a Hired Pen

I initially started what is now Notes from a Hired Pen as a blog on my own website, but when the newsletter trend kicked off, I moved it to TinyLetter. I figured, why not? It was free, and I never expected my newsletter to be more than just something I did for fun. 

But when Mailchimp bought it and then shut Tinyletter down, I panicked. It turned out I really liked writing my newsletter, I didn’t want to lose the archives, and I had monetized it by using it as a way to write a self-published ebook series with the same name.

I ended up doing what I should have done in the first place: I brought it back to my own website, and I now use Jetpack so that it runs as a blog and a newsletter. It’s now entirely under my control — and I was able to move over my archives. I will never have to worry about a newsletter company putting me in such a bad position again.

Jeremy Caplan
Writer, Wonder Tools

One mistake I wish I could take back is not hiring someone sooner to help with operations. 

Along with writing Wonder Tools, I host live subscriber events, create bonus online resources, syndicate my newsletter, and organize a variety of collaborations. That all requires logistics efforts beyond writing the words in the weekly newsletter. 

As part of that work, I’ve spent too many hours on logistics and little details. I should have devoted more effort early on to finding and training great people to help. I had lots of reasons for holding off on hiring, from wariness about spending lots of time training people, to concerns about handing over the keys to sensitive accounts to people I don’t know well. 

Over time, I’ve realized that these issues can be managed, and the benefits of freeing up time are important enough to merit some sacrifices. 

Julie Vick
Writer, Humor Me

One thing I wish I could re-do is my decision to add my humor writing challenge as a section to my newsletter. I set it up as a section that people could opt into because I didn’t think everyone in my audience would want to receive the emails. However, I’ve come to realize that the process for signing up for sections on Substack isn’t as straightforward as I would like it to be, and it caused some confusion. 

If I had to do it again, I think I would have just created a separate newsletter to make it easier for people to opt in or out. Going forward I’ll think about whether I want something to be a section of the existing newsletter or just a completely different newsletter altogether. I think there can be drawbacks to running multiple newsletters, but it can also have some advantages. 

Justin Kaufmann
Reporter, Axios Chicago

I love writing sarcastic, but sometimes it doesn’t read right. Once, I said, “inflation wasn’t a big deal for me because in Chicago, we already eat $20 cheeseburgers on the regular.” Instantly, my inbox flooded with people pissed at me and calling me an elite out-of-touch asshole. I just wanted to point out how ridiculous restaurant prices were already, but the way I wrote it made it seem like I only wanted $20 cheeseburgers. It was the first (and probably only) time I ever apologized for a joke.

Kevin Maguire
Writer, The New Fatherhood

They say when all you have is a hammer, everything looks like a nail. I started my newsletter after close to two decades working in the advertising industry and was instantly enamored with all the data at my fingertips — subscriber numbers, open rates, paid conversions, clickthroughs, referral patterns, forward rates, inbox placement. For the first few months of the newsletter, I was obsessed with them: How did one newsletter perform against another? What was the secret sauce to the perfect time to post? What mistakes would I make that would lead to dreaded unsubscribes?

It took me a while to realize that none of this mattered. Sure, it’s human nature to want to see numbers going up, and your lines to be going up and to the right. But it’s the effect, and not the cause. What I realized was most important was to really focus on what my newsletter was all about — who was I writing for? What problems were they facing? What did they need that they weren’t getting elsewhere? 

Two things became clear. First, there was a dearth of great writing about fatherhood. I didn’t think of myself as a writer, let alone a great one, but I believed if I put my focus purely on becoming a better writer, then it would deliver better results than focusing on any growth hacks. I bought a load of great books on writing and spent time reverse-engineering my favorite newsletters, trying to understand what made certain pieces land while others drifted past.

Secondly, I talked with many dads who all told me how isolating it can be to become a father. There are myriad social structures and societal norms that enable mums to support each other, but these things don’t exist in the realm of fatherhood. So, I decided that The New Fatherhood could become a space where dads could turn up and bring it all — the highs and the lows — to help each other out: not through metrics or measurements but through openness, vulnerability and shared experience.

Leonor Mamanna
Writer, Leave it to Leonor

I wish I hadn’t spent so much time on a newsletter-specific Instagram account. It took up so much time and seeped a lot of the joy away from the overall process and in the end, there was no reason for it. It didn’t get me a lot of subscribers, if any, and there was no additional value for existing readers. (Okay, admittedly, it looked great.) 

Lex Roman
Writer, Journalists Pay Themselves

I wish I had a paywall strategy when I launched. I started my latest project Journalists Pay Themselves in March 2024 and I didn’t launch a paid subscription until November. It’s funny because I cover how other publishers run subscriptions and paywalls but I put off my own monetization for several months and then, had to rethink how my editorial strategy and subscription strategy could work together. 

It’s not like these things aren’t flexible to some extent, but as you build your audience, they develop expectations for what you deliver. Especially with paid subscribers, they have reasons for paying you, so you can’t change it up on them too much, too fast, or you risk losing your base. 

Now, I’m working out how I want to balance “free” posts which are actually sponsor-backed and “paid” posts, and I will find a new rhythm with it, but it would definitely have been easier to think through it earlier.

Marc Pierre
Writer, Raising Myles

I am an open book. I believe the experiences we go through are meant to be shared, as none of them are truly unique. They serve as reminders or testimonies that we are not alone — that others are either enduring similar struggles or have already made it to the other side. That is how I see things through my rose-colored spectacles.

However, not everyone shares this perspective. Being vulnerable and honest comes with its challenges. Early on in my newsletter, I had to unpublish a letter I wrote when I was feeling alone and deserted. In that letter, I unintentionally hurt my family members and my wife. While that was never my intention, intention does not matter when you hurt people.

I have learned that not everything needs to be shared in the letters I write for my son for the world to see — I get to control the lens. 

I am grateful to have learned this lesson when I had only 300 subscribers, and not 3,000. Now, when I have doubts about clicking the publish button, I run it by my chief editor of staff — my wife.

Nick Hageman
Co-founder, KC Daily

I’ve made a lot of mistakes writing KC Daily, but this one may be the biggest.

I got a head start writing KC Daily for Monday after the Super Bowl on Friday. I wrote the subject line and preview text assuming the Chiefs were going to win.

The Chiefs did not win.

Late Sunday night, after the game, I finished writing and updating Monday’s newsletter. I deleted any reference to the Chiefs winning, double-checking the entire email. One small problem: I forgot to sync the change I made to the email preview text. It read: “If you’re reading this, the Chiefs are World Champions!”

I may be the reason the Chiefs lost Super Bowl LIX.

Sonia Weiser
Writer, Opportunities of the Week

I didn’t take the time to set up a real business and consequently for the entire time I was running the newsletter, it was through a very rudimentary set of systems. That made it incredibly challenging to adapt to a growing audience and streamline certain processes like payments. 

I wish I had preemptively treated the newsletter like a viable income stream and regulated everything from the jump.

Rameel Sheikh
Writer, The Bottleneck

Pricing psychology is everything. When I first launched a premium version of The Bottleneck, I assumed that because the free version was growing fast, people would naturally want to pay for an upgraded version. I focused too much on the value I saw rather than what subscribers actually needed to justify the purchase. I priced it based on gut instinct, not research. It flopped. 

Looking back, I should have applied the same operational mindset I preach — run small tests, gather data, and iterate. Now, every monetization experiment starts with deep audience insight. If I’d done that earlier, I would have saved months of effort and a lot of unnecessary second-guessing.

Wesley Verhoeve
Writer, Process

One mistake I wish I could take back is not thoroughly researching the technical limitations of the platform I use to publish my newsletter before launching a paid tier. While the platform works well for many use cases, it turned out to be less flexible than I anticipated when I wanted to offer additional features for paying subscribers, specifically adding perks only accessible to yearly subscribers. Since then, I’ve had to get creative, MacGyver-ing my way to a solution that’s only just okay.

Looking back, I wish I’d spent more time exploring the platform’s full capabilities (and limitations) so I could have built a smoother, more scalable solution from the start. It’s something I’ve learned the hard way, and it’s definitely influenced how I approach new projects now.