What I've learned after a year of serious Substacking

How to fix... James O'Malley.

A photo of me, yesterday.

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Dear subscribers,

One year ago today, my life changed forever.

It was the moment I finally hit the “activate” button on the paid tier of my Substack, and was when this newsletter became more than just a hobby – but a serious part of my career.

It was a big moment for me. Within the first week or so, over a hundred of you signed up for a paid subscription, and the numbers have continued to climb in the right direction since. My career was instantly transformed, and I had a business model to do more of... whatever this is.

It couldn’t have come at a better time for me personally. Though I was enjoying working as a freelancer, regularly writing for a number of people and outlets that I love, in truth I was in a bit of an intellectual and professional rut. Most of my work fell under the radar in terms of ‘the discourse’,¹ and I was getting too old to chase the ever-diminishing pool of freelance cash paid out by major publications.

So having had your support to turn Odds and Ends of History into a going concern has been incredible.

Over the last year, I’ve had an opportunity to write about a wide range of topics that would never make it past a traditional editor – like the time I argued that the British government should buy Twitter, or the time I picked a fight with the New Statesman. Oh, and all of the stuff about postcodes. I’ve also broken some stories along the way too.

Just as importantly though, it has been hugely rewarding. Because of my writing on here, I’ve had opportunities to talk to and meet with some brilliant people – and more broadly, it feels like people are interested in what I have to say – and it has given me the opportunity to participate more fully in political and policy debates.

In other words, it has been quite a turnaround for me. And over the last year I’ve learned a lot.

So I thought to celebrate a year, it might be interesting (or perhaps catastrophically self-indulgent) to turn my analytical lens on… myself. In a similar vein to my pieces on how to fix Newsnight and why it would be smart for Owen Jones to embrace capitalism, here’s five things I’ve learned in my first ‘proper’ year of Substack.

1. My career is in a much strategically stronger position than ever before

For the past decade or so, I’ve been a freelance writer and journalist. What this typically meant was that day to day, my job was to have an idea, pitch an editor at a publication – and hope that they would pay me money to write it for them.

By its very nature, it’s a hugely precarious business. You spend time building relationships with editors, but inevitably they will eventually move on to other jobs, and suddenly a regular source of your income goes dead. And similarly, some editors have just ghosted me without explanation².

On one level, this is just how the business works. This is the career I’ve signed up for. But in more recent years there are two mega-trends that have made the long term prospects for this sort of freelancing, with my mid-tier professional standing, even worse.

First, there’s the reality that the money in traditional journalism has fallen off of a cliff because of the economics of internet. This has only really gotten worse over the years I’ve been working. Publications that I’ve written for over the years have regularly had budgets slashed or disappear overnight.

It might surprise you to learn that until recently, I was the regular technology columnist for the magazine Readers’ Digest UK – but one day it just… ended because the money ran out.³

Until recently however, there was a solution, of sorts, to this problem: You could sell out, and cross the floor to work in PR or communications.

I’ve seen this happen to journalist colleagues repeatedly over the years, and frankly I don’t blame them for doing it. Even though speaking truth to power is, on paper, a high-status job – the reality is that The Man pays better and more reliably.

I’ve sold out a bit over the years myself, earning a proportion of my income from ghost-writing boring copy for corporate websites, or writing adverts for people. It doesn’t feel as morally pure as ‘real’ writing, but hey, I have a mortgage to pay.

However – now even this sideline is doomed, thanks to the second mega-trend. Which is, of course, AI.

Inevitably, as I’ve argued both here and elsewhere, AI is likely going to destroy basically all “lower tier” writing. If you need some pablum to fill space on your website, why would you pay me when ChatGPT can do the same job for cheaper?

Taken together then, these trends mean that ‘journalism’ – like writing up tweets about BBC Breakfast – and corporate writing are going to disappear as sources of income. Unless you’re a superstar writer, the long term economics of what you do are not looking good.

So you can see why, from a strategic perspective, having a moderately successful Substack has been so transformative for me.

Thanks to this newsletter, I now have some protection against both of these forces, because I’ve found an audience that is mine⁴. It’s not mediated by other editors or brands. If you’re reading me here, it’s because you’re interested in what I, specifically, have to say. And my authenticity, as a flesh and blood human, is a core part of that appeal – which is a quality that AI cannot replicate.

And from a business perspective, it has also been good for me. Instead of relying on the precarious patronage of a handful of editors, my income has been diversified – and is now the sum total of many smaller payments from many, many more people.

This feels like a more robust business model, as unless I write a truly horrific take⁵, it’s unlikely that significant numbers of you are going to cancel at exactly the same time.

So as strange and risky as launching a Substack may seem, I really do think this has put me in a strategically stronger position over the longer term⁶.

2. Substack aligns the incentives for me to do my best work

I’m going to be honest with you. Over the years when I have been freelancing, I have perhaps not always done my best work.

When I started my writing career, churning out articles for search engines to find, with titles like “Top 10 iPhone cases 2013”, I was not imagining a rapturous critical reception at my prose. Instead, my main goal was to hit the necessary word-count as quickly as possible, so that I could bank my £40 and move on to the next piece.

Though I take somewhat more pride in my work today, where I typically work on less depressing articles, what remains true is that not all words are not created equal. The time and effort required to write, say, a thousand words can vary enormously. Sometimes you just want to get to something good enough to before your deadline – because even if you spend double the amount of time finessing every word, the fee at the end is ultimately the same.

However, Substack is very different.

Here, my professional success is closely linked to the quality of work that I’m producing. There is a direct correlation between the quality of my writing and the number of new subscribers (both paid and free) that I earn after each post.

This is a good thing, as this aligns my incentives to produce quality content, because the more effort I make, the more I will be rewarded. That’s why I genuinely think that my writing on this newsletter has been some of the best that I’ve ever done.

However, there are also downstream consequences of this that are less helpful: Though I still have deadlines writing on Substack, they are self-imposed. I aim to write something every week (and I mostly have), but because I have the flexibility to spend extra time making sure that what I’m putting out is the best it can be, it does mean that I’m incentivised to let publication dates slip.

That’s why some weeks I’ll post on a Monday (that means I got it done with relative ease over the weekend). And other weeks I’ll publish… much later. Which implies a more torturous writing process.

3. Writing a long essay every week is hard

I’ve been incredibly lucky in life. Day to day, I don’t experience any real hardships, nor do I have any dependents (other than two cats). My working life is spent mostly tapping away at my computer, in my home.

Many other writers are in a similarly fortunate position, which is why I find it utterly nauseating when they complain about the burdens of being a writer. Because in objective, material terms there are few cushier jobs, and we have it easier than almost every other human ever born.

But this all said, I’m now going to be a little nauseating, as I still find writing hard.

Sadly, I’m not as gifted as, say, Matt Yglesias. My brain just isn’t ruthlessly efficient enough to blitz out an incisive 1500 word take every day of the week.

Instead, sometimes the writing process is a case of torturing the words out of me – and that my optimal working hours, when my brain is most driven to work, is sometimes late at night, rather than during the much more sensible 9-5.

Plus what adds to the writing challenge is that the format I’ve stumbled into on this newsletter is pretty long essays – typically 2000 to 3000 words in length. Annoyingly, writing 2000 words is not like writing two 1000 word pieces – the complexity scales more geometrically, so that a piece twice the length may take three times as long to complete.

And not to mention almost every piece I write tends to have a core idea at the heart of it, meaning I can’t just barf out the copy. I need to put on my “insufferable twat” beret and spend time thinking, to get the thesis straight in my head before doing the actual typing part.

I know, woe is me, right? To be clear, I’m not complaining. This is by some distance the most rewarding writing I have ever done, and as I say above, it’s amazing I get to do it.

But it is also time consuming. So it means that the stakes are raised a little when I start writing a piece. Sometimes I’ll spend two days working on something, before losing faith in the core idea or metaphor, and decide to scrap it, leading to lost time, and more of delays getting something out to serve my audience – which itself is genuinely stressful.

As a result of all of this, the moment I hit “publish” is my favourite part of the week. Not just because it is exciting, and that I get to read your feedback, but also because it’s like a pressure relief value. I finally get to relax and decompress. And then I can start worrying about what I’m going to write next week instead.

4. Churn is killer

Something I’m very conscious of with this newsletter is that I don’t want subscribers to think of their subscription like they’re doing me a favour. I don’t want people to pay out of a sense of charity, or because you know me in real life, and it would be awkward not to.⁷

Instead, I want readers to view this newsletter as a quality product. I want it to be something that you pay for because you find the content valuable and enjoy reading it.

However, because I’m very much not a charity also means that I also face the same business challenge that every recurring revenue business does: Churn.

Essentially, I have two major business priorities: Persuading you to subscribe in the first place, and persuading you to stick around once you’re here.

The first is honestly slightly easier than I expected. When I publish something suitably attractive, like, say, a piece slagging off the Good Law Project, a number of people will finally pull out their credit card and jump over the paywall.

But as things stand, only around half of those people will stick around for the long term.

My one strategic weakness is that I’m currently only really able to publish about once a week. For all of my bluster above, writing here still only pays for around two days a week of my time – meaning that I need to spend the rest of my time on other projects.

This isn’t a problem in one sense – because I love working with my other regular clients.

But it does mean that if there is a week long gap between publishing, then inevitably a few people will churn, and cancel their subscriptions.

That’s why I used to more regularly produce a bonus mini newsletter containing interesting links – to provide a little extra value and to appear in inboxes for a second time in the week. But I haven’t been able to do them recently, because I realised it was taking pretty much a working day to produce in itself – which is time I could instead be spending on the core essays.⁸

So one strategic goal I have for year two is figuring out if I can reduce this.

5. This is basically my dream job

In August last year, I sent out an email to my subscribers.

“This is the dream,” I wrote, asking whether readers would be willing to pre-pledge a subscription to turn this newsletter into a career reality. And I used that word deliberately, as this really is a dream job. I get to write about the topics that interest me, to an audience who are interested in what I have to say. And it pays some of my bills. What’s an astonishing privilege.

And sure, I still have career ambitions. I’d obviously like my audience to be even larger, and I’d like to earn more money from doing this (is this a good time to gently urge you to take out a paid subscription if you haven’t yet?). But fundamentally, writing this newsletter is basically the career I have wanted since I became a professional writer.

So I’m going to end by being weirdly sincere on the internet.

This is all thanks to you. It’s only with your support that I’m able to keep writing on here every week. And I feel extremely lucky that I get to do it.

To my subscribers who have supported my work over the last year, thank you.

James

1. Tragically when you’re as brain-poisoned by Twitter as I am, attention feels almost as important as money.

2. Though I’ve worked with many great editors too, I hasten to add!

3. The first I heard was seeing the editor posting about needing a new job. And there wasn’t even enough money left with the liquidators to pay my final two invoices… and I’m only a bit grumpy about this.

4. The absolute best thing Substack does is let its writers export their mailing lists. This means that unlike building an audience on other social media platforms, you’re not locked into their platform. This is great for writers, as it means that if the owner turns into a mad, brain-poisoned conspiracy theorist, you can escape elsewhere. And it’s good for Substack too – as it means what’s keeping me here is the quality of Substack as a platform, so the company is incentivised to keep making it better, and not using it for rent-seeking.

5. I know I just linked to my “neurodivergence” take as an example of something obviously controversial, but the actual reality is that my audience is so heavily self-selected, that I haven’t received a single angry response about it, and a whole bunch of people have said they agree with me.

6. And I haven’t even mentioned how this is also insurance against Twitter – my primary marketing tool – disappearing – as now I’ve got an alternative route to reaching my audience.

7. Though if this is the case, er, please don’t cancel. Think about how intensely awkward it would be for you to cancel now!

8. Does anyone miss me doing these? Let me know in the comments.