50 lessons learned from writing 50 newsletters

Reading time: 18 minutes

This week marked an important milestone: I just sent the 50th edition of Maker Mind, a newsletter about mindful productivity. Countless hours of careful writing, thoughtful conversations with readers, and exploring strange rabbit holes to report back on what I learned. While I believe the best way to learn is to experiment for yourself, I wanted to share some of the key lessons I learned from sending 50 newsletters.

Maker Mind Newsletter #50 Screenshot

Whether you currently run a newsletter or are thinking of starting one, I hope you find these thoughts helpful.

1. You don’t know what you don’t know. That’s called the Dunning–Kruger effect. Newsletters are an evolving space. There is a lot of contradictory and complex information out there—it’s easy to get paralysed. Don’t try to figure it all out in one go. Only do research on a “need to learn” basis.

2. Choose a topic you care about. Building a newsletter takes time. Don’t choose a topic to write about just because it’s trendy. Trends come and go, but your interest in the topic of your newsletter should last for long enough for you to provide value to your readers.

3. Or choose several topics you care about. It can be hard to pinpoint one single topic to write about—and that’s alright. The Maker Mind newsletter is about mindful productivity, creativity, mental health, and entrepreneurship. Having several topics of interest makes it easy to always have ideas to write about.

4. Focus on the right goals. Don’t give yourself a goal of reaching a certain number of subscribers by a specific date. Instead, make a pact with yourself of sending a specific number of newsletters by a specific date. For instance: “I will write one edition every week for the next twelve weeks.” Khe Hy says that 25 editions is the magic number—which is about half a year for a weekly newsletter—and I tend to agree.

5. Set expectations. Clearly state what the frequency and content of your newsletter will be. Do this for yourself and for your readers. The best time to set expectations is when you design your subscription page. Take the time to figure out exactly what you are offering to your readers and why they should subscribe—these will constitute your North Star over the long term.

6. Be realistic with your time commitment. These expectations should include how often you will send the newsletter. Decide whether you want to send your newsletter daily, weekly, bi-monthly, or monthly. While quality daily newsletters have the highest engagement rates, it may be hard to maintain such a schedule. It’s better to send one excellent newsletter every week than one low-quality newsletter every day. Find your balance.

7. Make it easy to subscribe. Beside the subscription page, add a link to your newsletter everywhere you are interacting with your audience: on each blog post, on your social media profiles, in your email signature. Writing great content is the foundation, but do make sure to provide an easy way for people to hear more from you.

8. Make it easy to unsubscribe. Don’t hold your readers hostage. Most people expect to find a link to unsubscribe at the bottom of a newsletter. Leave it there, don’t make it unnecessarily small, and don’t use guilt-inducing vocabulary to make people feel bad about clicking the unsubscribe link. 

9. Time blocking is essential. In order to stick to your schedule, don’t just wait until you find some free time during the week. Block time to work on your newsletter. Depending on the kind of newsletter—for instance curating links, long form commentary—your time-blocking strategy may vary: 20 minutes every morning? Two hours each week? Whatever your strategy, put it in your calendar so it’s easy to stick to your schedule.

10. Embrace flexible consistency. Despite setting a realistic schedule and blocking time to work on your newsletter, life happens—and you may miss an edition of your newsletter. Don’t beat yourself up. It’s better to send the newsletter a bit late than to not send it at all. And in certain circumstances, it’s also fine to make the choice of skipping an edition. Just be transparent with your readers.

11. Don’t be afraid to pivot. This is especially true in the early days of a newsletter. While it’s better to stick to a topic or a set of topics for long enough to build an audience, it may be that these topics don’t make sense for you or your audience anymore. Maker Mind was initially called The Creative Nomad and had a much bigger emphasis on traveling the world. I decided to pivot when these topics didn’t align with my lifestyle anymore.

12. Make new friends. Writing a newsletter is one of the best ways to have 1:1 online conversations at scale. Encourage readers to reply, and build relationships with them. Some of them may even become friends!

13. Be part of an ecosystem. Running a newsletter may feel like you are building in a silo, but it doesn’t have to be. Celebrate other people’s work that’s relevant to your audience’s interests: link to other people’s content, include shout outs, or collaborate with other writers. In my case, I interview prolific creators who I think Maker Mind’s readers may enjoy learning from. Holloway does an amazing job applying this principle to their excellent newsletter, Good Work, where they invite guest writers to some editions. (here is the one I wrote)

14. Spread the word. While word of mouth is powerful, don’t only rely on your readers to share your newsletter. Do some research to understand where your audience hangs out, and share your newsletters that are relevant to your audience on these channels. In my case, I often share my articles on Hackers News, Indie Hackers, and relevant Slack and Telegram groups.

15. Respect the reader-writer contract. Subscribers give you access to their most intimate space on the Internet: their inbox. Respect their trust by delivering exactly what you promised. If it’s a weekly newsletter, don’t spam them whenever you think of something interesting to share. If you said you would not sell their email addresses to anyone, don’t partner with a sponsor who requires such information. You may have to turn down some opportunities, but respecting the reader-writer contract is crucial to keep the trust of your audience.

16. Think long term. Corollary from the previous point: avoid “quick wins” at the detriment of long term sustainability. That random but lucrative partnership you have been offered? It may be better to turn it down. That suspicious giveaway you could run to collect lots of email addresses? Don’t.

17. Be selective with sponsors. It’s exciting the first time you receive a message enquiring about sponsorship opportunities, but it’s better to not get carried away. I have turned down many sponsorship offers because it was not a good fit in terms of what the Maker Mind readers would find valuable. Be mindful of who you work with. For instance, a simple accounting software run by a privacy-focused founder sounds great, but it wouldn’t work for Maker Mind.

18. Newsletters offer an answer to the starving writer. Many writers struggle to make ends meet. While freelance journalism often means spending lots of time pitching articles and working with a team of editors for weeks before an article is published, newsletters offer a sustainable way to generate revenue, either via sponsorships or paid memberships. If you already write online, consider starting a newsletter as a way to build a sustainable revenue stream.

19. Your newsletter doesn’t have to be “just” a newsletter. While a newsletter is a product in and of itself, it is also a distribution channel for other products you may want to share with your audience. Think of ways you can create more value, such as extra content, consulting, a podcast, an ebook, a course, or maybe an app. Dan Shipper from Superorganizers is doing a great job here with micro-apps for productivity, such as Sparkle to automatically keep your file system clean.

20. Go beyond one-way broadcasts. There are several levels of interaction you can build with your newsletter. The first level, the simplest and most common, is broadcasting: you send an email to your list, and that’s it. The second level is a two-way conversation, when you invite readers to reply and you reply to them. The third level is a network, where you encourage readers to connect with each other. For example, Maker Mind has a private community with virtual meetups, discussion forums, and a matching service.

Newsletter: from broadcast to network

21. Ask for feedback. Beyond welcoming feedback, be proactive and ask your readers to share their thoughts. It doesn’t mean you should implement every single suggestion, but feedback is precious and can inform your long-term strategy.

22. Don’t feed the trolls. When you ask for feedback, you will receive some unconstructive comments, where the intention is clearly to hurt your feelings or to pick a fight. Ignore these. They’re not worth your time and your mental energy. Please note: trolling is mostly about the intention behind the comments. Sometimes your feelings may get hurt despite the best intentions—that’s not trolling, it’s just harsh but potentially useful feedback.

23. Keep it simple. A newsletter doesn’t need to have lots of bells and whistles. From design to content, keep things simple. While the typical user experience may change in the future, at the moment newsletters are mostly text-only. You want it to be easy to read whenever your subscribers decide to open a new edition. Avoid inserting too many images, or videos which may not be supported in their email client, or using an overly fancy design which may look weird in their email app. A simple user experience will help let your content shine.

24. Keep it fun. A newsletter is a sandbox—a space to playfully experiment. As long as you respect the reader-writer contract, it’s okay to try new approaches. Want to explore a new format? Maybe add a new section? Don’t feel like you have to apply a strict framework. Your readers signed up to hear from you about specific topics and with a specific frequency. There is space for creativity beyond this simple agreement.

25. Work with the garage door open. Working in public is one of the best ways to build authentic connections with your readers. Share your process, lessons, and plans. Especially for solo newsletters, readers often care about the content as much as they care about your work as a person. Keeping the garage door open creates more opportunities for meaningful discussions with your readers.

26. Keep it human. It’s okay to talk about personal stuff from time to time. When my grandma passed away, I shared the experience with the Maker Mind readers. It’s also okay not to talk about personal stuff. Again—as long as the reader-writer contract is respected, you can decide whether or not to share more personal aspects of your life with your newsletter subscribers. Whatever you decide, remember it’s a human-to-human relationship.

27. Ideas are everywhere. I used to wait until it was time to sit down and write to try and come up with ideas. Relying on flimsy inspiration didn’t work so well—I often ended up staring at a blank page. Instead, it’s much better to write down ideas as you go about your life and work. Jot down a quick note whenever you have an idea, when you read something new, or when a friend mentions something interesting. It’s easier to tap into that ever-growing list of ideas than to come up with something new on the spot.

28. Manage your impostor syndrome. Many creators suffer from impostor syndrome—the fear of being exposed as a fraud. Sometimes, you may hesitate to send a newsletter because you’re stretching yourself out of your comfort zone. Send it anyway. See yourself as a work in progress, practice just-in-time learning, ask for help when needed, and fail like a scientist.

29. Celebrate your achievements. Again, building a newsletter is a project that requires patience. There’s no real definition of what “success” looks like for a newsletter. All the more reasons to celebrate your micro-wins. Did you just send your 10th edition? Did you reach 100 subscribers? While these numbers don’t intrinsically mean anything (see next lesson), do give yourself a pat on the back. 

30. Not all numbers are made equal. Newsletter writers can get obsessed with the size of their email list. But the number of subscribers is largely a vanity number. Similar to buying fake followers on social media, it doesn’t matter if you have millions of subscribers and nobody opens your newsletter.

31. Don’t get obsessed with stats. Even open rates don’t mean much today. Many people are using apps and browser extensions that block any form of tracking, so these numbers are increasingly becoming meaningless. Focus on creating great content and engaging with your readers—these are the only meaningful goals to work towards.

32. Each subscriber is unique. Some readers will be highly engaged—replying to each edition, sharing it with their friends, sending feedback. Others will feel like anonymous ghosts. And that’s alright. Everyone engages with online content in a different way. Don’t try to push all of your audience to actively engage. Let them participate on their own terms so they get the value they seek.

33. People are busy—and their inbox is busier. Make your readers’ life as easy as possible. Include a reminder of what the newsletter is about, keep it short, include links so they can save the content to read it later. Your newsletter should be a source of value, not a burden.

34. Tools don’t matter that much. Many people spend a lot of time figuring out the perfect tool(s) to launch a newsletter. However, the highest impact action prospective newsletter writers can take is to… Just sit down and write their first newsletter. Pick a tool, put up a landing page, and send your first edition. Once you get to a certain number of subscribers—or if you want to build a proper funnel—you can spend more time figuring out the optimal tooling. 

35. It’s a marathon. Growing a newsletter takes time. If the goal is to make money online, there are many quicker, simpler ways to achieve that goal. Running a newsletter is not a get-rich-quick scheme. Be patient.

36. Each new edition is an opportunity to improve. You won’t get it right straight away, and you can’t get it right all the time. Maker Mind is currently in its third iteration in terms of content and design. It’s a learning process: make sure you listen and adapt.

37. Proofread like your life depends on it. Unlike a blog post, there is no edit button when you send a newsletter. If there’s a typo, or something that could be misread, it’s too late to fix it once it’s in your readers’ inbox. Read it once, re-read it twice, proofread it thrice.

38. But don’t sweat it if you make a mistake. Despite your best care and attention, you will make mistakes from time to time. Your readers know there is a human being behind the newsletter. If you make a mistake, you can always include a correction in the next edition.

39. Writing subject lines is an art. The single biggest factor when people decide whether or not to open your newsletter is the subject line. It’s worth spending a bit more time crafting a subject line that reflects what’s inside. I like to keep mine short and I always add a little emoji. But do experiment to see what works for your newsletter—the subject line is an art, not a science.

Newsletter subject lines - Maker Mind

40. Keep on showing up. Some weeks will be better than others. You may have one edition going viral, bringing lots of new readers, and weeks where it almost feels like talking to yourself. Ignore the ups and downs: just keep on writing and providing value without paying attention to the distracting noise of these daily fluctuations.

41. Don’t stress over unsubscribers. When it comes to newsletters, the reader-writer relationship is bidirectional. Both the writer and the reader need to keep on showing up. If a subscriber decides they no longer want to show up, that’s fine. As I mentioned before, it doesn’t matter if you have millions of subscribers and nobody opens your newsletter. See unsubscribing as a friendly way to say: “Thank you and goodbye.” (not to mention that many email service providers charge based on your number of subscribers, so as a reader unsubscribing is also a way to help the writer save money)

42. Make your newsletter privacy-friendly. Whether you are based in Europe or not, there is a lot to learn from GDPR. A reader recently shared how happy they were about the privacy-friendly experience when signing up to Maker Mind. It’s worth investing a bit of time to implement double opt-in and to make your privacy policy human-readable.

43. Ask for help. The basic skills to run a newsletter are fairly simple: sign up for an email service provider, create a landing page for people to subscribe, and consistently send your newsletter following a realistic schedule. But once your audience starts growing, you may want to explore more ways to deliver value or reach more readers. As with many crafts, things can get complex. Don’t try to do it all on your own—ask for help. Find your tribe. That’s why I created the Newsletter Geeks group on Telegram, where newsletter writers help each other figure out the best strategies to grow their newsletter. There is no need to go alone.

44. Comparing yourself to others is a waste of creative energy. It can be tempting to look at other newsletter creators and compare your results to theirs—maybe they have more subscribers, or they send their newsletter more often. While there is a lot you can learn from other creators, don’t turn it into an imaginary competition. Channel your mental energy towards creative work on your newsletter. And if you have any mental energy left, consider helping fellow newsletter writers!

45. Use your newsletter as a self-education mechanism. It can be hard to stay motivated when you want to teach yourself how to do something new. A newsletter is a great way to make yourself accountable. Want to learn how to code? Start a coding newsletter. Want to learn how to cook? Share a new recipe every week in your newsletter. The journey is more exciting when you’re learning alongside your readers.

46. Learn new skills beyond writing. While learning something new is a great excuse to run a newsletter, running a newsletter is also a great excuse to learn something new. You will naturally pick up some marketing, communication, design, and planning skills. Running a newsletter is a Swiss army knife of creativity.

47. Invite participation. Featuring your readers in your newsletter is a great way to foster a sense of community. Every time a reader sends me something interesting I think other readers will benefit from, I include it in the “Brain Candy” section of the newsletter. If one of your key goals truly is to share the most interesting content about a specific topic with your audience, make the most of the extra pairs of eyes.

48. Make space for self-reflection. Because newsletters offer such a seemingly simple recipe—pick a topic, write about it, stick to a schedule—it can be easy to get into a mindless grind, sending edition after edition without ever stopping to reflect. It’s good to pause and think from time to time: is the newsletter still aligned with my goals? Are there any adjustments I need to make? Make sure to pause and reflect.

49. Make yourself proud. Ultimately, writing a newsletter is still writing. It’s a creative process. You will make mistakes, and you will learn as you go. It’s a good sign if you look back and cringe when re-reading old editions—it means you are growing as a writer. But always strive to send work that you are proud of at the time. It’s the best way to make progress.

50. There is no magic formula. These are 50 lessons I learned from 50 editions of my own newsletter—while I believe many of them are applicable to most newsletter writers, there is no step-by-step playbook one can follow to run a successful newsletter. As with many creative projects, running a newsletter is all about experimentation. Embrace the uncertainty and have fun—it’s worth it.

I think the first and the last lessons are the most important ones. You don’t know what you don’t know, and there is no magic formula. If you are currently running a newsletter or thinking of starting one, the best way to figure it out is to experiment for yourself. If you do, please let me know!

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