running my newsletter

I got a couple of questions about my newsletter recently, so I thought I’d write up how I’m thinking about it these days.
You can subscribe to the newsletter in question here.

why’d I start a newsletter?
Super pragmatically: I started running the email marketing product at Mailchimp and had to know it intimately. 

But even if they’re not your literal job, there are other great things about newsletters: 

  • Good way to stay in touch with farflung friends 
  • People generally no longer visit blogs directly 
  • I saw some marketing advice that stuck with me: the only 3 ways you can reach your audience directly are through email address, phone number, and physical address. Any other way, you’re relying on other entities to allow you to get through. Having seen favorite creators really struggle with algorithm changes, that stuck with me 
  • Unsubscribe buttons are great! Gives me confidence that I can email directly without bugging people. 

What’s in my newsletter? Why’s it different than the stuff on my website?
I feel weird about archives and how most stuff on the internet is archived by default. I try to keep posts on my site only as long as I agree with them and remove them once I disagree. That’s why I’ve generally hidden timestamps on my site, and my tweets auto-delete after a few months.

Each issue of my newsletter is writing that’s specific/exclusive to the newsletter. They are not archived, so you’ll only ever see the ones sent while you were subscribed. This lets me write about more ephemeral pieces of my life: who and where I was, what I felt, etc. 

All of the above is kind of strange and I’ve gotten pushback on this! 

Some people have told me they won’t subscribe unless they can preview an issue. (I’ve bowed to pressure and put one issue up, to try out how it feels.) 

Others have said that they didn’t subscribe because they assumed it’d just be a rehash of everything on my site. I’m thinking through how to signal this more clearly.

I ignore most stats. I don’t optimize for open rate. Sometimes I look at which links were clicked most to gauge what interests people. 

I try not to sweat unsubscribes. I’ve had 4 unsubscribes over the last 2 years and 200+ subscribers. I’d prefer to ignore these entirely, but they are a helpful cue of who maybe wants a bit less of me. 

This is a very friends and fam newsletter. I write it to be great for someone knows me but maybe hasn’t caught up with me for a few months. 

I feel like I can be more open since I’m writing to a closed audience, on personal stuff like how I’m feeling at work. I think people would also be interested in hearing more about stuff like dating, but I feel squeamish about that.

Given how intimate I want it to be, it’s a little unusual that anyone can sign up. Out of 200+ subscribers, I’d estimate ~15% are people I’ve never met. I welcome that – if anyone wants to come along for the ride, by all means! I’m not trying to aggressively grow, but I would want anyone who wants to keep in touch with me or learn more about me to subscribe. 

In my dream world, all of my friends would have a monthly/quarterly newsletter! I think it’s wild that we stay in touch through random dribs and drabs on social media, and I like being intentional about what I’m sharing about my life. 

Newsletters come out each season: every 3 months. I block off time in my calendar as a target publish date.
2 weeks before the issue comes out, I start a note in Simplenote jotting down ideas. 
A few days before publish, I’m certain I have absolutely nothing to say! 
I push through, write a bunch, read over it the next day, and cut a bunch (about ⅓ every time. I felt bad that my most recent one was longer than my normal ~1000 word issue. Snackable newsletters are the best!) 
I assemble it (and jot down feedback/suggestions for the Mailchimp team 🙂 ), check it on phone and different email clients, check all the links a million times, then hit send and try not refresh obsessively awaiting responses. 

All of this takes me probably 6-8 hours (slow writer and editor!).

how I feel about the content these days
Something tough I’ve noticed is, given my long drafting process, I edit out things that I don’t find interesting that day, and repeat over multiple days. This leads to only the most serious, lofty topics surviving. It hides how goofy I am a lot of the time! 

I also tend to hedge and write a bunch of different sections/lists per issue. 

I’d love to 1) send out some lighter issues; 2) try including different formats and types of media; and 3) write more single-topic issues. Maybe this year! 

how I feel about cadence these days 
I started out my newsletter as an ad hoc thing, where I’d only write if I had something important to share. I wanted to leave people always wanting more. 

Now that I moved it to being on a schedule, I do prioritize it way more and have ended up making issues I never would’ve if I kept waiting for inspiration. 

I’ve been reading lots of daily blogs and weekly newsletters and have been thinking about how different the expectations are. Lower production value, lower substance bar, way more sense of chumminess… I absolutely can’t commit to something that frequent, but I’ve been wondering what if recently.

audience reception
Getting replies makes all the effort abundantly worth it! Everything from fast replies that just say “let’s call soon!” to long, thoughtful replies way more beautiful than my original letter. Sometimes I get a response months later about how something in that issue stayed with someone. 

If you liked an issue, definitely occasionally hit reply and let me know! Every time I hit send, I’m like “why on earth did I just do that??” Since I started a newsletter and saw how much work goes into one, I’ve made it a point to respond occasionally to smaller newsletters and sometimes bigger ones to say thanks!

advice before starting a newsletter

  • Know what you want to get out of it! Staying in touch with friends vs just wanting a forcing function to write vs trying to get a book deal are super different games with different ways of knowing if you’re being successful.
  • Have a plan for at least your first ~2 newsletters. 26% of podcasts only ever had 1 episode published, and I’m certain it’s way higher for newsletters.
  • Cadence: I deeply recommend monthly or even less frequently unless you have a ton of time or a really lightweight format. 
  • Don’t sweat picking a newsletter service too much. The main difference is going to be how it feels using the product, and to a lesser extent, how much it costs and what % of emails get successfully delivered (these are unlikely to come into play if you’re doing this as a casual project like I am). 

Hope this helped! Happy to chat more on newsletters whenever: hi@

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