I mentioned a few months ago that I was tentatively excited to build out a little creative project that was definitively NOT a forever project. At the time, I didn’t want to share my vision too much because I was hoping that keeping it close to my chest would allow myself time to vibe with it, and maybe just not do it at all.

🥁 The project was: a sort of travel log of our recent trip to Japan, in the format of an email newsletter (yes, I started a Substack lol).

I stole used the general guide from Craig Mod’s post on pop-up newsletters and set a few ground rules for myself:

  • Post every day of the trip before I go to sleep
  • Post in the form of an email newsletter that friends can subscribe to
  • I only get three photos: a view, a vibe and a food (but as much text as I want)
  • Once the trip is over, that’s it, the newsletter is done and the subscriber list is deleted 💥

And damn it, I’m hooked.

It was even better than I expected.

Something to look forward to every day

I came to relish having a little bit of time at the end of every day (or in one case, the next morning), where I’d look back at all the photos I’d taken, thought about what had happened, and work out which could fit each of criteria. A nice way to unwind and savour the day.

I often suffer from travel FOMO and the urge to keep powering through fifty billion activities on a holiday. This practice helped take the edge off a bit, and I think I ended up benefiting from it on this trip.

The benefits of the email newsletter format

I had a hunch that I would like writing an email newsletter. Something that I didn’t expect (and I think that Buttondown nails this really well) is how much more I enjoyed this than basically any other format I’ve done in the past.

It was super calming writing in such a basic way - you only get so much customisation you can do, basically what’s in Markdown. I got really into the flow of writing this way, and it prevented things from spiralling out of control and getting super long.

It was satisfying receiving the emails myself, and watching the list of posts grow day by day, adding up to a corpus of photos and thoughts and memories that I can go back to in the future.

I didn’t get sucked into social media and the endless scrolling feeds - I pretty much stayed logged out of my Instagram account and got a really good break out of it.

The privacy of email newsletters meant that it felt intimate and that I could say a bit more than I would feel comfortable saying publicly. Something about knowing that what I was writing wasn’t going to be crawled by Google and maybe stumbled upon in the future and judged harshly.

Writing an email newsletter was small enough that mistakes weren’t a HUGE drama, and could easily get resolved. Very early on, I had issues with Buttondown’s confirmation email not working (basically a mistake on my end) and while I was figuring that out, I just…sent my friends the email in a giant BCC lol.

People seemed to enjoy it

I have to say - I expected no one to subscribe. I didn’t look at the list on the first day I sent emails out, and when I finally did (because I needed to troubleshoot something), I was really touched 🥺

And I got quite a few friends write to me about how THEY enjoyed it too! I was also a bit worried it would seem snooty or insufferable, but that wasn’t the case. One or two did make jokes about me starting a Substack though 😂 but that was fine!

A bit more on the software (Buttondown)

I used to work for an email marketing company, so maybe I have more thoughts on email software than most.

For me, it was no question that I’d use software to build and send emails for this pop-up newsletter. I don’t want to have to worry about deliverability or messing around with HTML while I’m travelling.

My first instinct was to use Tinyletter, which my friend Rory used yonks ago, for a little Pokemon newsletter. To my dismay, it no longer exists 😢

I signed up for Buttondown after that, on Craig’s recommendation (he uses my former employer’s software, but doesn’t recommend it for newbies to the scene, and I tend to agree). I really loved it in the end - it was perfect for what I needed.

When I was having issues with Buttondown and waiting for responses from support, I trialed EmailOctopus and Substack (ugh).

I found EmailOctopus to be too similar to Campaign Monitor, in that it’s very oriented around campaigns (email marketing), and much more clunky for my use case. I didn’t REALLY care about the design of the emails I was writing, as I was planning to send out one a day for ~22 days!

And as for Substack - I just didn’t want all the surrounding infrastructure that Substack brings to the table. I didn’t want comments, I especially didn’t want hosting of my emails, and I didn’t want randos stumbling upon my very first experimental email newsletter. I found myself lost in the settings when I started and quickly knew it wasn’t for me.

Wrapping up

I really wanted to share this in the hope of inspiring others to also give this a go. I really cannot recommend starting a pop-up newsletter enough. I suppose if enough people do it, maybe we’ll get sick of them - I doubt it though. They really are the best newsletters.