What I've learned growing a newsletter to 15,000 readers

Advice is cheap, so I'm giving you some reflections instead

I’m starting 2022 with over 15,000 newsletter readers. 

For those who’ve only recently started reading this weekly dispatch, I started writing a newsletter in the summer of 2017. I’d just been made redundant from my staff job as a news editor at an online magazine and I didn’t know what was next for me. As I wrote back then it was supposed to be a space to chart my journey of navigating unexpected self-employment. 

It was a crisis in my career that prompted me to start this newsletter and in many ways, it still is a diary of my messy feelings about work, writing and creativity. Memos about a career in flux, you could say. 

Before I get into the things I’ve learned about growing a newsletter, I want to first state that I’m fully aware that my advice is cheap. This isn’t going to be a list of strategies to get you to your first 1,000 email sign-ups in 30 days, because truthfully, I wouldn’t know what to tell you.

Naturally, people want advice from someone who’s already successfully done the thing they’re trying to do. I get asked about newsletter growth because I’m out the other side: I’ve grown a newsletter. No one was asking me for anything when I had 30 subscribers. 

Now, while I can talk about the mechanics of what I did, I can’t guarantee that if you follow that advice you’ll get to where you're trying to go. On a bad day, that makes me feel like a fraud. But logically I know that those sorts of blueprints are always pretty brittle. That’s because they’re context-dependent. For example, the context of this newsletter is that I started it four years ago; that’s very important to remember because that was a pre-Substack age and I got into the newsletter game on the ground floor.

So don’t read what follows as a blueprint, but rather a collection of reflections from which you can take what you like and leave the rest. 

You don’t need to worry about algorithms, but you need to worry about algorithms 

I’m on a 14-day streak of Wordle, the daily word puzzle that’s gripped the internet. It’s a really simple and unflashy game that has no ads and no push notifications. It’s down to you to remember to go back each day and play the next game. Its origin story is really sweet. 

Wordle’s grip on the zeitgeist has prompted me to think about internet trends, digital community and what makes something stick online. Like a newsletter, Wordle exists outside of social media’s algorithms, yet it is also entirely dependent on them.

Read: How I made my money as a freelance journalist in 2020

The game launched in October, but it only really took off when its creator introduced a way to share its results in an if-you-know-you-know way on Twitter. Similarly, on the surface, one of the greatest joys of writing a newsletter is the fact that it doesn’t depend on algorithms. Your inbox is chronological, nothing influences what gets to the top of it except timing. Sure, a good subject line helps with open rates, but honestly, some of the most successful newsletters out there have really obscure ones. 

And yet, it would be foolish of me to think algorithms play no role in the growth of my newsletter. When I first moved over to Substack, that’s when its growth started to accelerate. I can’t know this for sure but I highly suspect that its newfound shareability on Twitter really helped (hey! did you know you can share this newsletter on Twitter!)

One thing I do know for sure, however, is that after the email list itself, the biggest driver of traffic to my newsletter is Twitter. 

I don’t love that I need Twitter to help my newsletter, but I try to look at it as positively as I can. To continue with the Wordle comparison, I keep going back to play for a really simple reason: I just want to. Its creator, Josh Wardle, has said that he purposefully created the game in a way that doesn’t demand too much of your attention. Similarly, a good newsletter is a breath of fresh internet air. It offers you something that you can’t find elsewhere and also feels different in tone and style to what you’d find on a social media platform or even on an online magazine. It respects the fact it’s landing in an inbox, a sacred digital space.

But don’t kid yourself into thinking you can totally ignore those other parts of the internet. Because just as Wordle needed Twitter to propel it to stardom, a newsletter needs other platforms as well.

You don’t need a big Twitter following to do well at newsletters 

When I say that you need to use Twitter to promote your newsletter, I am not saying you need a big following on Twitter to start a successful newsletter. My newsletter sign-ups have always outpaced my Twitter followers. In my experience, at least, a big Twitter following is not a prerequisite to growing a newsletter readership.

When the technology writer and former New York Times columnist, Charlie Warzel, moved his newsletter over to the Atlantic from Substack, he said that he had 16,000 readers on his list. That’s basically the same size as this newsletter! And Charlie has 170,000 Twitter followers (I have 12,000 now and when I started my newsletter I had about 2,000). Obviously, I appreciate that it’s taken me four years to get to 15,000 and that Charlie got there in about six months. But the point is not to use the size of your Twitter following as a predictor of how your newsletter will fare. (Also, if you haven’t read Charlie’s outgoing post on Substack, do because it’s full of great observations about writing newsletters as a full-time job). 

Your most engaged posts will also be your most hated and in general, you won’t know why stuff does well until you send it 

There are some posts I write that I just ~know~ will do well. Eg, any time I write about money, and specifically how much of it I make, the post takes off. 

Then there are posts that get widely shared and commented on, which also result in the biggest number of unsubscribes. When I wrote about Gilmore Girls last year and all the ways in which I hate Rory Gilmore, it was one of my most-liked and shared posts. It was also one of the posts that saw the biggest dip in subscribers after I sent it out. (One day I’ll tell you the story of the newsletter that resulted in 300 immediate unsubscribes!!) 

Then there are the posts that don’t get that many public comments but prompt a wave of private replies (if you didn’t already know - you can reply directly this to email and it does actually come into my inbox and I really do read them all). The email I sent recently about how I felt making less money for the first time in my freelance business was followed by an outpouring of emails, many of them long and detailed, expressing similar feelings.

And then there are the posts that I just have no clue why they did well. My most popular, most read post of all time is one about writing with nine-inch fake nails. It doesn’t have that many likes on it and not a single comment but has over 25,000 views (and this was when my list was less than half the size it is now). I can only guess that it got posted somewhere on the internet.

I can’t know for sure, partly because Substack’s analytics aren’t that great. (My biggest bugbear with the platform). They’ve improved recently, but that post in question was from back in early 2020. However, I don’t think it’s fair to just blame a lack of analytics, because even so, there’s no accounting for dark social.

To bring all this back to my first point about cheap advice, one of the reasons I feel uncomfortable telling people how to grow a newsletter is because I don’t know how I grew mine. I don’t know how to say this without it sounding like a humblebrag, but I don’t know why 15,000 signed up for my newsletter. I don’t know why people read it or why it continues to grow. I have plenty of theories (aka this whole post) but I can’t say for sure. 

It’s boring, but consistency is the best strategy (that, and people do just want to relate)

Of all the reasons I think this newsletter’s grown, the one I’m most confident about is consistency.

I’ve tried lots of different formats, types of content and names for this newsletter but what’s stayed the same is that I’ve sent it at 2 PM on Friday afternoons for the last four and a half years.

Ok, there’s one more conclusion I feel pretty confident about: people want to read stuff that seems niche but is actually really universal.

The best newsletters read like horoscopes, you think they’ve been written specifically for you. This newsletter is ostensibly about freelancing. Except that’s not really what it’s about. It’s actually about shame, guilt, ambition, loss and belonging. Messy emotions that everyone with a human heart can relate to. 

My favourite compliment I get is from the people who tell me that they don’t freelance nor have any interest in freelancing, but still read my newsletter. I don’t know how I managed to get them regularly reading a newsletter about freelancing, but somehow I did and I’m so damn grateful to have you here.

Thank you for all your support these last four and a half years, it truly means the world to me. And now, time to tackle today’s Wordle. 🤓