Why I’m not sending evergreen emails anymore

I’ve been building an email newsletter since about 2015, and more than 20,000 people have subscribed to it so far, which is amazing.

But creating good content is hard, and it’s easy to feel like you’re on a treadmill if you constantly have to be crafting new content for an email list.

But then back in 2016 or so, I was seduced by a lot of writers and marketers talking about the idea of “evergreen content”. What if, instead of writing a new email for my entire list every week, I could just reuse all my best content for every subscriber who joins my list? Time-saving for me, and they’re getting my best content without missing anything, so better for them, right?

So I setup a new evergreen newsletter sequence in my email marketing software so when someone subscribed to my list, they would automatically get a series of my best content dripped out to them every week. When I kicked it off, I had about six months worth of content in there. I figured I’d just continue writing and add to that over time.

As I switched over to this strategy, my open rates and click-through rates stayed pretty consistently high. Everything was good, or so I thought.

Looking back at the last two years, I’ve realized that there are three problems with this approach.

Problem #1: Engagement will suffer in the long run

My first clue was that the number of email replies I’d get on Thursdays (when the newsletter goes out) was dropping. When I was writing and sending emails out live, I’d usually get 10-20 replies at least, and sometimes many, many more. And this was even when my list was small. Now I wasn’t getting nearly as many responses from a list 5x-10x as big, even though people were opening and clicking. It’s like they just didn’t feel as engaged with the content.

And over the long run, my open rates and click rates did slowly start to decline as well.

Looking back now, this seems obvious. People aren’t dumb, they can tell what’s going on, and they’re not a fan. No one wants to get an email every week with a link to an article that’s 2-3 years old. Boring.

Sure, they might read the article, but there won’t be quite that same “spark”. There won’t be a sense of joining something that’s active and growing and timely and fresh. And over time, they’ll just start to tune it out and drift away.

Problem #2: It made me lazy

I made this shift to evergreen newsletter sequences back in 2016, and like I mentioned above, I had about six months of content queued up, with a plan to add more every week. After all, if I just kept writing my weekly newsletter every week, after a year I’d have 18 months of content (the original six months plus another year’s worth).

Guess how many emails I added to that evergreen sequence since 2016?


Literally, until a few weeks ago, I hadn’t written a single article or newsletter email since mid-2016, except for a product launch or other event.

That’s so sad and embarrassing and pathetic that I don’t even want to publish this.

The reality is that as soon as I put those emails into that evergreen sequence and flipped the switch, a switch flipped in my head too. I no longer had that pressure every week to create something of value for my audience.

As anyone who creates content on a regular basis will tell you, that pressure is stressful. You will often want to escape it. You’ll dread it many days.

But what I’ve come to realize is that the pressure is vital. It’s part of showing up every day for the people you serve. And when it’s gone, so is that connection that you had with the audience.

And that brings me to the biggest problem of all with this evergreen newsletter strategy:

Problem #3: It’s disrespectful to my readers

Ultimately, I did this because I was focused on me. I was focused on how I could make my life better, not make life better for my readers.

And that’s dumb. The subscribers to my email list are the backbone of my entire business. I’ve made hundreds of thousands of dollars selling courses, coaching, and other products to this list, and I don’t have a couple hours per week to write them a fresh email that adds value to their life? That’s pathetic.

It’s a huge show of trust and respect for someone to subscribe to my list, and I’m genuinely sorry for abusing that trust by taking my subscribers for granted. Those evergreen newsletter emails I sent out were good, but they weren’t my best. Worse, they stopped a long time ago for most of my readers, because I didn’t keep adding to the sequences.

To cut myself the tiniest bit of slack here, I think a lot of this stems from a good place that’s grounded in my background as a software engineer. It’s in my nature to try and make things more efficient, to automate things, to streamline them so I’m not spending more time doing it than necessary. It’s dumb to setup hundreds of servers by hand when you can write some code to do it in a more repeatable, error-free way automatically.

But I’m dealing with people here, not servers. And the emails I send back and forth with my readers every week are part of a relationship that we have, not just a one-way channel for notifications about old articles (cringe).

My pledge: no more evergreen newsletter emails

A few days ago I shut off the evergreen sequence and sent the first non-sales email to my entire list that I’ve sent in more than two years. It took hours to write, format, setup in ActiveCampaign, and carefully test before hitting send.

It felt great.

I got dozens of responses, despite sending it later in the day than I should have (not used to how long it takes to write one of these!).

This is my new normal.

To be clear, I’m going to keep doing onboarding sequences, because I think there is value in sending a few days of “kickoff content” to introduce readers to my writing and what I teach.

But I won’t be doing evergreen newsletter emails anymore. Every week, I’ll be writing a fresh, exclusive email to go out on Thursdays. I won’t outsource them for someone else to write. And I won’t share them anywhere else.

It’s the least I can do.