How to kill a newsletter

Plan Your Next: Letter No. 18

Well, hello there, old friend.

Is it hard to believe that 609 days have passed since I last graced your inbox? I sure as hell do. I thought about it every Sunday.

Before sitting down to write today, I looked up the last article I wrote to jog my memory. As it turns out, writing a transition about Tim Ferriss and micro-dosing is much easier than trying to stitch together 20 months of silence.

Before I start to talk about the near demise of this newsletter, there were many people who reached out to support me after I cooled off. Thank you. One friend mentioned, “Keep writing Nate, even if I don’t take anything away from it.” A true friend. I’ll be sure to use that testimonial in my marketing materials later. (:

I don't want to spend too much time circling high above 10,000 feet thinking about all of the missed conversations we should have had. Because I truly miss that aspect. But I miss writing this newsletter, even if it’s just for me.

So what the hell happened?


⏳ Tl;dr

A quick interruption for those who forgot who I am, or those that are new. I’m Nate, a designer writing a weekly newsletter about being mindful of what’s next for us. We chat about shared interests in reading, careers, productivity, design, and travel. Remember doing that?

Future newsletters will be focused in the same way, except much shorter. This letter is the exception to that rule. The bulk of my writing is now happening on my new site. In fact, I wrote three new articles that I’d love for you to check out!

With that out of the way, let’s talk about how to kill a newsletter.


Step 1: Think you’re above the chaos

There’s a flicker of panic when you know a routine of yours is about to get disrupted. Maybe it’s reading, writing, or working out. This happens often enough, so you probably have a good idea of how you're going to respond. It's different for everyone, but usually, we see it coming.

I handle most types of distractions fairly well. But, coming back from a trip, moving apartments, injuring myself, a looming pandemic, or when our car decides to break down, the next couple of domino pieces seemingly push themselves over.

The author Nassim Taleb talks a lot about this idea of being antifragile in his book of the same name. He says, "Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty."

In the same way that our bones can grow stronger due to external load, our ability to deal with chaos grows stronger by repeatedly exposing ourselves to randomness.

What happened to me personally was that we moved in early 2018, and that threw my routine into a mess.

Simply, I am not antifragile.

Step 2: Set ambitious goals

First of all, I felt the need to write incredibly long articles every week. This weighed on how I approached reading.

I read almost every book I could find on how to become a better writer. Those books were what I thought I should be reading and it was hard to do this and read the things I wanted to read.

I also hoped that I could maintain a pace at which I'd be able to stick to. Once the excitement wears off, you're left with the habits that you built up to that point.

That flicker of panic appeared before I published that last newsletter 87 weeks ago, right before we were planning to move apartments.

I remember thinking that #17 might be the last that I would write. I hoped that feeling of shame might only last a week or two, but the first domino had already been tipped. Next, we moved and that eventually started the collision.

James Clear, the author of Atomic Habits says, "The secret is to always stay below the point where it feels like work."

My habit was there, but my expectations were flying too far into work territory. I needed to lower the bar.

Step 3: Stare at a blank screen

Many times I would sit down on a Wednesday or Thursday night and stare at a blank page, not having anything to write about. I hadn't developed a dependable system, and trying to remember the things that I read during the week was essentially lost.

David Perell is a writer who talks quite a bit about writing from abundance, which is exactly why I’m in the middle of taking his course. He mentions frequently that when you sit down, 80% of your writing should already be done. You should be writing from an abundance of material that you have already captured.

By focusing your time reading only the things that you want to write about, you're curating your inputs. If you build up your information capture system in this way, you should already have ideas and notes for you to pull from when you sit down.

My info capture looks like this

WTF? I know that it looks complicated but most of it’s automated. The key tools I use are handwritten notes, Instapaper, Readwise, and Roam. It’s fairly easy for me now to sit down and capture a few ideas at the moment, when reading the things that interest me.

What's going to change?

While it might not feel different from this article, I'll be paring back the length of these newsletters and sharing shorter summaries based on what I'm reading. My focus will be on longer-form writing on my own site and blog, which leads me into my next thing...

A new site, and three new published articles!

I’ve owned my web presence for 20 years now. I was just going back through some embarrassing pieces that I’ve written. Wow, Nate, you got really personal. That’s sketch.

I love being the master of my own domain, but until now, writing consistently has evaded me. Hopefully, that’s changing.

I've written three new articles recently. The first is The most important thing you can learn about design. The second is how to Read more by reading slowly. And lastly, Communities warped by design.

The last is the most somber of the trio, but I learned quite a bit about the city I grew up in researching this and its uncomfortable past.

I’d love it if you read them and let me know what you think!

What I'm thinking about this week

Roam Research is marketed as a networked tool for thought. It emphasizes bi-directional linking to make it easy for ideas to collide within your notes. I'll write more about this another time, but for those who hate organizing notes and finding folders for your mind dumps, this might be useful to you. I’ll admit the onboarding and design are in rough shape, but it’s a very early company. Reach out if you have any questions about it.

Robinhood is one of the most beautifully designed products for trading stocks. I've been using it for about 4 years now, and they led the charge in removing broker fees from stocks and options. But, sometimes great design can have horrible outcomes, and sadly they have been in the news with how easy they make trading on margin feel like a game.

👋 One more thing

While I did everything I could to kill this newsletter, I’m grateful I didn’t. If you have any thoughts, reply directly or comment directly using tiny little comment icon below.

See you next Sunday!