Today marks the day that I’ve been sending a newsletter for 52 weeks straight. 

(Okay, well, if we’re being honest it’s been 52 newsletters in 53 weeks because there was one week where I got sick and felt crappy and decided that wellbeing was more important than sending a newsletter… but still, I’ve sent 52 freaking newsletter emails out and that’s pretty rad.)

And in sending a newsletter every week for 52/53 weeks, I’ve learned a whole lot. Not just about the technicalities of writing a newsletter (like making sure your subject lines are interesting AF or why having a newsletter outline is ridiculously helpful), but also why it’s dang important to not put so much damn pressure on yourself and to remember that you’re just a human being writing to other weird and wonderful human beings. 

And I’ve boiled all of my biggest takeaways from sending 52 newsletters down into 26 brilliant and insightful (hopefully) lessons for you to enjoy. 😘

(P.S. I should have included a lesson about finding the right email service provider because I first started out by TRYING to use Mailchimp which immediately made me cry. So if you want an email service provider that’s easy as hell to use and makes really pretty emails and has awesome analytics, check out Flodesk! And you can use my affiliate link to get 50% off an entire year. Feel free to thank me later.)

26 Lessons from Sending a Year’s Worth of Newsletters 

1. Share about yourself 

This may or may not seem like the most obvious “duh” thing in the world, but something I’ve learned over and over again as an entrepreneur is that people are hungry for personal stuff. Don’t be afraid to include the details of your life, the stuff you’re up to, or the ridiculous memories you have of your parents growing up—it helps build such an honest and real connection. And using stuff from your own life experiences gives you an endless bank of stories to pull from… 

2. ANYTHING can be a newsletter 

You can turn any semi-interesting life occurrence into a juicy newsletter that’s not only a great story but also contains a valuable lesson. 

• Spilling a gross amount of tuna salad in your backpack on the first day of high school? → A lesson on the importance of first impressions 
• Your dad accidentally throwing his wallet away and having to dig through a gas station trash can for it? → The importance of trusting your intuition and never giving up
• Getting a flat? → The frustration you feel when a biz investment you made doesn’t go the way you wanted it to

If you ain’t got any newsletter ideas, start paying attention to anything remotely out of the ordinary in your life. I promise you, you’ve got good stories unfolding all around you. 

3. Write to one person and make that one person your best friend 

If you have a hella professional business and are all about being buttoned up and formal, then you probs don’t want to take this advice. But if you ended up on my blog (The Copy with Spice Blog, just in case you actually weren’t sure where you were), I’m guessing that’s not your style. So my advice for you my dearest, loveliest human… keep your writing casual and conversational. 

And if it helps, just imagine you’ve called your best friend up and are telling them this hilarious story about something that just happened to you. Because that’s the type of relationship you want to build with your subscribers—one that feels intimate, fun, and full of the kind of tea you only spill to your best friends.   

4. Always write down all of your newsletter ideas—quality or not

Any time anything remotely interesting happens to me that I think could be a creative newsletter idea, I write it down in my Notes app. 

I also usually forget to include enough context so when I come back to the note later on, I find myself staring at something that says “itty bitty titty committee” and realize that I have no idea what I was talking about or how this could possibly be turned into a newsletter worth sending. BUT. When I do it right and I write down a good enough description that I can come back to and remember the brilliant idea, it’s ridiculously helpful. 

Pro tip: if you’re using the Notes app, write “newsletter idea” somewhere in your description so you could later search for “newsletter idea” in your Notes app rather than be forced to look through each and every note you’ve ever left to yourself.

5. Think about what you want your content to be about ahead of time 

Okay, I swear, I’m not a procrastinator but for some reason when it comes to sending my newsletter, I write it last minute almost every week. An approach I strongly DON’T recommend. However, the only reason this ends up being usually okay for me is because by the time I’m actually sitting down to write my newsletter, I’ve already been thinking about it for at least a few days ahead of time. 

I almost always know what next week’s newsletter is gonna be about (and if you’ve got a launch coming up, you’d want to be far more strategic than that) and I’ve found that having a week to think about it means I’ve got my ideas pretty well sorted before I sit down to write. Which helps me when it’s 7 pm on a Wednesday night and I’m scrambling to finish my newsletter for Thursday morning, yet again.

6. Limit the amount of time you give yourself for writing your weekly newsletter 

A task will fill to fit the amount of space you hold for it. It’s actually a law. Parkinson’s Law to be precise. And it’s so damn true. If I give myself 4 hours to write my newsletter, it’s gonna take 4 hours. If I set a timer and do my damndest to write it in 1 hour, it’s gonna be wayyyyy closer to that. So don’t give yourself a ridiculous amount of time unless you want writing your newsletter to take a ridiculous amount of time. 

7. Stories win every time 

Recently, I asked my lovely subscribers about their fave newsletters and every single one of them mentioned the story—not the takeaway, not the lesson, not the actionable advice, but the story. And that’s because stories stick like song lyrics in your head. Stories are fun to read and hear. They are easy to relate with. And they’ll be the thing people remember after time has passed so make sure you’re using them. 

8. Writing a great short story takes a few key ingredients 

Writing a great short story takes practice, butttt a few things that help with telling stories in your newsletter are:

1. Start your newsletter off with the exciting action (for example: “I was sliding off the road”) 
2. But give enough background/buildup so that your readers give a crap about what’s happening and to help the pacing of the story (for example: after they know the car was sliding out of control, build the suspense for a little longer by answering where you were, why you were on that highway, what was going on just seconds before)
3. Don’t leave people hanging forever, let them know what happened (for example: let them know you didn’t crash the car so they aren’t left wondering)

And if you want, you can relate that whole story to a lesson. 

9. Consistency is powerful 

One time, one of my favorite people in the world (shout out Han) sent me a text that the very first thing she had gotten up and done that Thursday morning was read my newsletter. Besides making me ridiculously happy, her text also made me realize that consistency is powerful. Because when you pick a day of the week (and a time of the day to try and stick to), you can start creating anticipation. And when you can create weekly anticipation, you’re building a powerful relationship with somebody because they’re looking forward to when you pop up next. 

So if you’re gonna send a newsletter. Pick a day and a time and stick to it. And to make that easier on yourself…

10. Make sure you’ve got an outline to make sending a weekly newsletter a whole lot easier

I change up the bulk of my newsletter all the time. Sometimes it’s 3 tips. Sometimes it’s a sneaky lesson wrapped into the story. But I always have the name of my newsletter, a funny little blurb that hints at what the topic of the newsletter will be, and 2-3 “flavors of the week” that are either helpful resources, funny TikToks, recommended podcast episodes, books I’m reading, or whatever else. Like this…

And having this outline has helped me so much with not having to create my newsletter from scratch every week AND with sending a newsletter that looks familiar to everyone who reads it!

11. Think about the things you’re able to talk about a lot

This one relates back to consistency, too, because like I said, consistency is powerful. And that’s true about your newsletter topics as well. It’s like in a good book when the same characters pop up and do that same silly thing that they’ve done before (like Neville in Harry Potter losing sh*t), it makes you—as a reader—feel like you know these characters damn well. And you can absolutely do that with your newsletter content too. 

I’m an anxiety girlie. I’ve got some wonderfully wacky parents. And I’ve got a sense of self-deprecating humor which appears in me sharing embarrassing stories about myself. And all of those things show up over and over again in my newsletter. As long as the stories are slightly different and entertaining, people will be delighted by the familiarity. 

12. Don’t be afraid to experiment

Listen, I’ve been sending a newsletter for 52 weeks (+ the one week I took off), and during that time I’ve tested out a whole lot. I’ve written longer newsletters. I’ve included personal stories. I’ve done more business advice-style stuff. I’ve changed the name of my newsletter. I’ve changed the day I send my newsletter. Long story short, I’ve done a whole lot of experimenting. 

And that experimenting has been awesome because it’s helped me figure out what I like which is really important to figure out if you’re planning on sending a newsletter out each and every week.

13. Remember that every newsletter you send doesn’t have to be perfect

Maybe you’re not a chronic perfectionist who worries that each and every thing she does must be a flawless expression to prove her worth to the world, but… I am. Or at least I was. And that pressure made writing my newsletter miserable at times. 

Some weeks are gonna be better than others. Sometimes people will unsubscribe. Some people aren’t gonna like the way you write or the things you talk about. That’s okay. Keep showing up and know that the people who adore you aren’t gonna leave if this week’s newsletter wasn’t as fabulous as the last. 

14. There is such a thing as sending a newsletter with TOO much value

And no, I don’t mean that in a giving-away-free-content way because giving away free value is amazing. I’m all for that. But, when you’re trying to jam-pack each and every email you send so that it’s the most value-packed newsletter in the world and you’re worried that if it’s not the bestest newsletter in the world, people will unsubscribe, you’ll become penniless, and the global economy will likely fail… see #13. 

One tip, one laugh, one “huh, I hadn’t thought of it like that” is enough. You don’t need to offer your subscribers an entire world of info in a mere few hundred-word newsletter.

15. Always treat your newsletter subscribers like VIPs

Fun fact, I actually wrote an entire newsletter on this very idea. (And if you haven’t read it, you should, because it’s funny and informative. The balance I always aim to strike. )

Buttttt…. If I had to summarize the idea for you in a speedy, fast manner it would be this: your subscribers are like dear friends who adore you, who adore what you have to say, and who actually listen to you when you talk. You better treat them with the respect they deserve by giving them inside deals, first access to spots/waitlists/whatever, and sharing with them your personal secrets. 

They’re oh-so-special and absolutely deserve to be treated that way. 

16. People love when you include receipts

And part of treating your subscribers like VIPs is giving them the inside scoop on you and the foolish mistakes you’ve made like me buying an RV and trying to renovate it. And if you’ve got a personal story that you also happen to have photo evidence for… include it. It will make your story that much better.

17. Use first names sparingly 

Yes, using someone’s first name is an awesome way to make a newsletter subscriber feel like “hey! That’s me!” But if you use their first name too much it starts to feel… wrong. 

“Listen, Alethea. There’s something I’ve got to get off my chest” = fine.

“Listen, Alethea. There’s something, Alethea, I’ve got to get off my chest, Alethea” = serial killer creepy. Use the [First Name] option mindfully to avoid scaring off your subscribers.

18. Break text up 

People are often reading your newsletter on their email app on their phone and that means that a 4-sentence paragraph can look like a 24-sentence paragraph. So make sure to be generous with hitting the enter button AND breaking up sentences into bite-size pieces. You’re not sending a newsletter that’s an experimental piece of literature, so make sure it’s actually easy to read. 

19. Read it out aloud and add some italics to keep it interesting

17 paragraphs of stiff and robotic sentences can get hella boring. But 17 pieces of hilarious, conversational writing can leave your readers hungry for more. The best way to make sure your email is more like the latter is to read your newsletter out loud and notice the places where you emphasize a word. If you draw out a word like butttttt, throw in some more ts to the end of it. Screw grammar. Write the way you would if you were having a conversation. 

20. Give your newsletter subject lines the attention they deserve

Yeah, you might feel like it makes the most sense to spend 95 percent of your time writing your newsletter and then 5 seconds on your subject line, but what’s important to remember is that if people aren’t intrigued enough to open your newsletter, they aren’t gonna read all of that beautiful stuff you wrote. 

Some of the subject lines with the best open rates that I’ve had have been:

• Welp, THAT definitely horrified some older folks
• The worst investment I ever made
• Don’t dump your BF on your period 

Feel free to copy the style and make it your own. 😘 

21. Tell everyone about your newsletter until you’re blue in the face

Just about every week I tell people to sign up for my newsletter on Instagram. And even though I’ve said it one bajillion times. And I feel certain that there can’t be a single person on earth who follows me and hasn’t heard about my newsletter, every week I’m proven wrong. So go out there and tell people to subscribe (and remember that no one is paying as much attention to how many times you promote yourself as you think they are).

22. Get as many people to unsubscribe as possible 

Fran, from The Passions Collective, told me something brilliant that totally changed my mindset about unsubscribes which was that unsubscribes are freaking awesome. Because if someone doesn’t like what you have to say in your newsletter they sure as sh*t aren’t gonna like working with you. So instead of sulking in the corner about being rejected, celebrate the unsubscribes. They’re just helping you narrow down your list to the cream of the crop peeps.

23. Don’t be nervous about sending a promotional newsletter (or not sending promotional ones either)

When people sign up for your email list, they know at some point you’re gonna sell them something, so don’t feel weird about telling people about your services/sales/products and promotions. And if those people don’t like it and unsubscribe, read: above. But also, you don’t have to sell. In my newsletter, I keep it chill. Sometimes I promote my offers sometimes I don’t. And despite ACTIVELY selling or not, I do get clients from my email list. So you do you, boo. 

24. Screw the shoulds, write the way you want to 

THERE’S NO RULEBOOK FOR WHAT YOU HAVE TO WRITE ABOUT. 

*Takes a sip of water and a deep breath*

Okay, but seriously, you don’t have to write about things you don’t want to. One time Jen from TONIC, who writes a hilarious and ridiculously long newsletter, said if she had to write about website templates each and every week she wouldn’t keep sending a newsletter, at all. So let this be your reminder that no matter what industry you’re in, there’s no topic you have to stick to.

25. And don’t feel like every time you send a newsletter it has to follow the same outline

Remember that whole thing I said about having a newsletter outline in #10? Well, there’s something else I want to add. Even if your newsletter has an outline, you can still change the structure up based on what you want to share. It doesn’t have to be three tips or a funny intro that always leads into a blog post. If that’s what you want to do because that excites you, hell yeah. 

But you don’t have to. You’re free to do whatever the hell you want. 

26. Last, but not least, you might surprise yourself when it comes to what you like

I didn’t LOVE sending a weekly newsletter when I started. In fact, when I’d hear other people talk about how email marketing had become their fav thing ever I was like… HOW?! But now…it truly is. 

I love getting to spend the week looking for newsletter-worthy events happening around me and getting to share ridiculous stories and thoughts with those on my email list. My subscribers have become precious and adored family members—I cherish each and every one of them.

So if you’re gonna try sending a weekly newsletter, try it out for a while because it might just become your favorite thing too. 

Bottom line?

This blog post was absurdly long, but hopefully absurdly helpful in thinking about sending a weekly newsletter of your own! And if not, I hope it was, at the very least, entertaining. Thank god, I didn’t try to go for 52 lessons, huh?

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