Reflecting on my four years on Substack

It's been a ride!!

Welcome to A-Mail. I’m Anna Codrea-Rado, a business, tech and culture writer. My current reporting obsession is how work makes us feel. The vibe of this newsletter is somewhere between a reporter’s notebook and an email to a long-distance friend. 15,000+ readers love it. Maybe you will, too?

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Illustration: Léo Hamelin

When I started my newsletter, it was B.S. Before Substack. 

I hate to sound like “I knew the band before they were famous,” but I knew the tech platform before the hype.

I’ve just celebrated four years¹ on Substack and I asked on Notes if people would be interested in a reflective post. I also realised that (duh) most of the people reading this newsletter now haven’t been here from the start so I thought I’d answer the question about growing as a writer by telling the story of my newsletter. 

💌 The Mailchimp era

I sent my first newsletter on a Friday afternoon in July 2017, exactly one week after getting laid off from my job as a news editor at Vice. 

I used Mailchimp (blame the Serial ads) and I sent my first email to about 50 people and asked them to sign up for more. About 30 people did. Looking back, I've tried to maintain that same emailing attitude ever since. I'm emailing people that I know, but not that well, and I want to respect their inboxes.

Back then, it was called Cod Philosophy – a naff play on my internet name and pop philosophy. I made a bad logo in Canva. I convinced my friend Léo Hamelin to illustrate it and I’m so glad I did manage because I think the cartoons are what make my newsletter feel distinct.

I also included pictures of my dog, Dolly, in my early dispatches because I wasn’t confident enough that people would want to read what I had to say… so I gave them something cute to look at.

Here’s a pic of Dolly for old time’s sake… she turned 15 this May <3

Figuring out what I wanted to write about took a while. At the time, I’d been a music journalist who didn’t actually write about music, but rather the culture around it. I wasn’t sure what my Freelance Niche™️ was yet, so I tried out different things. Early posts included: attempts at cultural commentary, rants about the state of the media and curation of internet links.

Soon, my natural propensity for meta-analysis bubbled up and I started writing about the BTS of my freelancing. At some point, I sent out an email asking readers what they liked hearing from me about – the resounding response was more stuff about freelancing.

Call it retroactively fitting a content strategy but after that, I started planning out my newsletter posts. I used Trello as a content calendar, with columns for ideas, scheduled and published. I planned my content out a few months ahead. And I always sent my newsletters on Friday at 2 PM. (Who was she and where did she go??)

I’m way less consistent with my posting schedule these days. I also don’t really plan my newsletters out anymore; I do still send them out on a Friday afternoon, though.

🚀 The Professional Freelancer era 

I hit 2,000 readers by the beginning of 2019. That was the threshold for Mailchimp before you had to pay to use it. I started looking into ways to monetise the project. I ran a sponsored post with a mobile banking app – it was a Q&A with an accountant about freelance tax questions and they paid me £1000. 

Call it serendipity, but around that time I was working on a project with Robert Cottrell, the creator of The Browser newsletter². I was telling Robert about my newsletter and how I wasn’t sure what to do with it and he said, “Just put it on Substack.” I didn’t know what he was talking about, having never heard of Substack before; I assumed it was some kind of offshoot of the coding platform Stack Overflow. No, he explained, it was a platform that lets you monetise your newsletter through subscriptions.

He talked about it like it was a no-brainer and encouraged me to reach out to Hamish McKenzie, one of Substack’s co-founders, directly. The team was tiny enough for Hamish to personally take my call.

He convinced me to move to Substack not because he’s a great salesperson (which he is), but because his why for starting the company resonated deeply. He too was a frustrated writer who just wanted to get paid for his work. The way he talked about the cultural and economic importance of writers was inspiring and he promised to help with my launch. I was in.

So in May 2019, I re-named my newsletter to The Professional Freelancer, moved it over to Substack and “went paid”. 

Hamish coached me through the roll-out. First, I told readers I was going paid, then I reminded them about it and then I actually did it. I vividly remember being unable to do anything else that day because I was so nervous. And then, once I’d pressed send, I was glued to my screen as I watched about 50 people sign up immediately. By the end of the roll-out, I was up to nearly 100.

At the beginning of 2020, my newsletter was thriving. I kicked off the year with a pitching challenge. Paid subscribers got a structured pitching sprint where we got together and sent out five pitches a week for five weeks. 

I got up to 350 paying subscribers (out of a total of 5,000 readers). At its peak, my newsletter brought in £4,000 a month in revenue. But I was also struggling to keep pace. I was kinda white-labelling the Substack product – my offering was more than just additional newsletters, it also included live events and in-depth resources.

My newsletter audience has grown steadily over the years

😷 The Pandemic era

Then came March 2020 and my paid subscribers plummeted. My audience – freelancers, journalists and freelance journalists – were among some of the hardest hit in the early days of the pandemic. I also couldn’t deliver on my product – a membership that included in-person events; I tried to switch to virtual but couldn’t quite make it work.

My janky subscriber revenue from May 2019 to now

The pandemic wasn’t the only problem I was facing. Around this time I also started working on my first book, You’re The Business, a freelancing handbook. I landed that book deal because of the newsletter; using new media to bridge the gap to legacy publishing was perhaps my proudest newsletter moment.

However, while I was working on the book I didn’t have the resources (neither financial nor energetic) to also write my newsletter. So I put it on pause. And then after the book came out, I thought I had nothing left to say about freelancing. What I realise now is that I was burned out.

So I pivoted once more. I changed the name again, this time to Lance, and I went back to my journalistic roots to campaign for better working conditions by reporting on the stories the mainstream media was missing. I spent a lot of money on new branding and a custom domain name because I wanted to Invest In My Media Business.

I published some excellent pieces in this era because I worked with other freelancers on them. I commissioned Amelia Tait to investigate a question that I’ve been dying to know: can influencers expense their Boots hauls? I hired Emilie Friedlander to edit a series I wrote about the impact of the pandemic on freelancers.

People were starting to take notice of my newsletter. I got an email from one of my media idols, Martin Lewis. I didn’t believe it was him at first, I thought it was some weird scam. Politicians shared my stories.

But regardless of all of that, I still couldn't make the numbers work. The economic implications of the pandemic were only worsening. My business costs were higher now because I was trying to pay writers and editors a decent rate. I was also exhausted and running on fumes. Also, if I’m totally honest, while I’m convinced that Lance was a good business idea, it wasn’t the right one for me.

🌪️ My chaotic email era

I changed the newsletter’s name for a THIRD TIME. This time to A-Mail because I just wanted something vague enough to accommodate my ever-changing interests. I limped along, sending a handful more newsletters but I was out of steam by then. And it showed in my emails.

I started dreading sending my newsletter and I felt like I had no other option but to stop writing it altogether.

Then, in June 2022, I sent an email announcing that I was quitting my newsletter.

And…. then I came back again. At the end of last year, about six months after saying I was done, I quietly reneged on my dramatic exit.

🔮 And that brings us here, now

It was only THIS WEEK that I fully appreciated just how much my writing has improved as a result of these newsletters. I filed a personal essay to an editor and she didn’t change its structure. You don’t get more of a writing compliment than that because it basically validates that the version of the story that was in my head is one that the world also deserves to see. 

It also made me realise how I’ve been shaming myself for “only writing newsletters”. The longer I’ve freelanced, the less I’ve written for trad media –and there’s a small part of me that’s bothered by that. I have an ego that seems to only be massaged by bylines in old newspapers and magazines.

That being said, there’s also been an important shift in my approach as well. Whereas before I would put things in my newsletter that didn’t fit anywhere else, I now pitch out the stories that don’t fit here. Call it my newsletter-first strategy.

OK WOW, THIS WAS SO LONG. I guess I’ve been around here for ages. I might do a Q&A about what’s like to be a Substack dinosaur, but in the meantime – I’d love to hear which era you joined me on my newsletter journey? LMK!!

1. I thought it was five when I started writing this email… four isn’t as numerically satisfying, but I’d already started on the post so here we are.

2. The Browser is no longer on Substack but I’m forever grateful to Robert for that conversation!!