My learnings a year into writing a paid newsletter

What I’ve learned about the newsletter business, plans for the coming year, and some numbers.

Sep 07, 2022

👋 Hi, this is Gergely with a bonus, free issue of the Pragmatic Engineer Newsletter. If you’re not a full subscriber yet, you missed the issues Internal politics for software engineers and managers and a few others. Subscribe to get this newsletter every week 👇

It’s been just over a year since I sent out the first issue of The Pragmatic Engineer Newsletter. I’ve already summarized all the articles written in year one and they add up to nearly five books’ worth of writing! In this issue, I share how the newsletter is going, what I’ve learned, and my plans for the next 12 months.

We cover:

An unlikely career change: why I started the newsletter
How the newsletter is going: with numbers
Editorial independence and the ‘no sponsorships’ policy
‘The Scoop’ and the pull to become more of a journalist
What I’ve learned about readers
What I’ve learned about the newsletter business
Plans for the next year and a new holiday policy

tl;dr

tl;dr stands for “too long, didn’t read.” When I worked at Uber within software engineering, a habit caught on. Emails longer than a few paragraphs would start with a tl;dr – a summary of its contents. Given this update is also long, let me use this approach.

Going forward, paying subscribers can expect two articles per week. This is more than the one article per week when the newsletter started a year ago.
On Tuesdays, you’ll get a long-form educational / practical article. On Thursdays, you’ll get a ‘newsy’ article about what’s been happening in the tech industry - typically, The Scoop. On Wednesdays – less frequently – you might get a bonus article. This update about the newsletter is an example.
I now have a holiday policy. During the last week of the year, there will be no articles, and during four weeks of the year there will only be one article per week – the long-form one on Tuesdays.
The Pragmatic Engineer is the best, most fun job I’ve had, and an unlikely career change. Thank you for your support which makes this business viable!

1. An unlikely career change: why I started the newsletter

I left my job as an engineering manager at Uber in October 2020. My plan A was to write a book for six months, and then found a startup solving a problem in the space of platform engineering and – probably, hopefully? – raise venture capital to kick it off. Plan B was to join a company as an engineer or engineering leader, if founding a startup didn’t work out.

By the summer of 2021, the first part of my plan – the book writing – had gone well. I had published three books: The Tech Resume Inside Out, Growing as a Mobile Engineer and Building Mobile Apps at Scale. However, I was getting uncertain about whether I should found a startup, or keep spending more time on writing.

At the back of my mind, I’d been considering starting a weekly, paid-for newsletter for many months. The two things that held me back were:

Can I write sufficiently in-depth articles on a weekly basis?
Would I have enough topics to cover?

Looking back on the number of books I published gave me confidence that #1 – writing – wouldn’t be a problem. I also had a backlog of ~100 topics gathered over a few months, so #2 was no longer an excuse.

I sensed there was a gap in the market for regular and fresh insights into practical software engineering and ‘Big Tech topics.’ When I transitioned to become an engineering manager at Uber, my manager told me to find and expense a weekly or monthly publication that could help me grow professionally as an engineering manager. After doing research, the best I could find was Harvard Business Review. Still, while I subscribed for two years, most of the writing did not resonate with me.

I figured, ‘perhaps there are enough experienced software engineers and engineering managers working at Big Tech or fast-moving tech companies who face the same challenge.’ So, I decided to write the publication I wish I could have read when I joined Uber – and especially when I became a manager.

On 26th August 2021, I announced the launch of The Pragmatic Engineer Newsletter. I have a confession to make: at this point I was still unsure if I’d manage to build a viable business. To stay grounded, I gave myself six months to give it 100% of my time and focus, and then would check in on how it was going.

If I had any doubts about business viability, this soon changed. A month into starting the newsletter, it became a Top 10 Substack technology publication, six weeks after launch it hit 1,000 paying subscribers, and four months after launch The Pragmatic Engineer became the #1 technology newsletter in the Substack chart. Read the review of the first four months of the newsletter in the article The Pragmatic Engineer in 2021.

2. How the newsletter is going

Every week, more people read the newsletter than before. Today, there are more than 150,000 subscribers – both free and paid subscriptions:

I personally don’t think the numbers tell the whole story behind the newsletter. Numbers are reassuring because they’re easy to interpret. However, I pay just as much attention to the messages which readers send me via email and social media on why they find the publication helpful.

Several readers share how they are looking forward to new issues, or find the newsletter useful in learning more about the industry, and use it to level-up their knowledge. An engineering manager shared how the newsletter keeps them up to date with new developments in the industry, and even attributed their success in getting a Software Development Manager (SDM) role at Amazon to regularly reading – and reflecting on – the contents. Here are a few more nice reviews of the newsletter. Thanks for these!

Writing The Pragmatic Engineer is my best job, to date. I loved working as a software engineer and shipping interesting and challenging projects. Building Skype for Xbox One from idea to shipping on launch day is still one of my fondest memories and Uber’s YOLO app rewrite is a project I’ll never forget. I also found the challenge of becoming an engineering manager and navigating a large company to be an interesting one, especially working on the Payments team at Uber, and being involved from before a project was even an idea, all the way to shipping it.

There are many bubbles in the software engineering industry, and if you’re outside of one, you find yourself in an information gap. Big Tech and fast-moving startups are a bubble: once you’re in, you realize why certain things work as they do. Like the curious absence of Scrum at these places.

The Pragmatic Engineer newsletter gives me an excuse to talk with insiders and to research topics which are more or less taken for granted within Big Tech. Even when working at Uber, I would share some insights, but I never had time to write more than two or three articles per year on my blog. By working on the newsletter full-time, this is up to two a week!

A year on, I’m even more excited about the publication than when I started. The backlog of topics has only grown and my network of people who are open to helping with industry insights keeps expanding. There’s so much to cover in the coming year!

The reader base is far more diverse than I expected. The “core” audience I write for is software engineers and engineering managers. However, I get messages from other tech professionals: data scientists, data engineers, product managers and managers in technology – but not software engineering – who are also avid readers. I’ve also learned recruiters and HR professionals find the newsletter is relevant for their work.

3. Editorial independence and the ‘no sponsorship’ policy

The newsletter operates with no sponsorships, affiliates or third-party ads. When I launched the publication, my goal was full independence, funded solely by subscribers.

Looking around at how technology newsletters operate, the most tempting way to monetize any tech publication is through sponsorships. There’s no shortage of marketing money that tech companies, startups, and SaaS companies are willing to pay to get the attention of technology professionals and decision-makers – you! — in order to raise awareness of their products and ultimately drive sales.

My goal has always been to say “no” to this enticing revenue stream. This is because of the incentives that relying on ads brings, which get in the way of true independence. Publications which depend on ads need to optimize for broad reach and serve their advertisers by reaching the audience that is their target market. For such publications, the true customer is the advertiser and not the reader. But I want to optimize for depth and not worry about reaching a specific demographic that some advertiser cares about. I also want to avoid the bias that advertising money might bring; the perception that I’d cover a company more favorably because they pay me.

I now have an ethics statement to clarify that I do not accept any form of payment to write about companies or products, don’t do sponsorships, advertisements or affiliate links, including on the free newsletter. I extended this ethics statement to include everything I write and have removed all affiliate links from across my blog and YouTube channels – which generated $25,000 over two years – and all third-party advertisements from my blog.

The free version of the newsletter still has advertisements for my other business. At the bottom of each newsletter, I list featured jobs from The Pragmatic Engineer Job Board and mention The Pragmatic Engineer Talent Collective as a vetted place to either hire or get hired, as an experienced software professional. The paid newsletter does not contain this.

A special thanks to subscribers who pay for the publication, or expense it as an educational resource. If you’re planning to expense the publication, you are welcome to use a variation of this email template.

4. ‘The Scoop’ and the pull to become more of a journalist

I originally started The Pragmatic Engineer newsletter as a single deep-dive article, every Tuesday. Over time, I’ve added more columns, delivered on Thursdays.

The Scoop was the first such regular additional column and I have a reporter at Wired magazine to thank for it being born.

In August 2021, a journalist reached out, who was writing about the crazy hiring market for tech talent. They asked if I had comments on the situation. I replied with a few pages of insights. However, by the time I sent this email, the article was already live on Wired. When reading the Wired article, I felt the piece missed all the insights I’d observed and shared.

I turned my original reply into an article and published The perfect storm causing an insane tech hiring market, which described what was happening in the heated hiring market, why it was happening, and offered immediate advice to hiring managers on how to retain talent and hire in that environment. This was a paywalled article and it was not until six months later that The New York Times covered the same topic, in which the recruiter the NYT interviewed shared the same observations about the competitive nature of the job market that I’d covered, months back.

It felt to me like there was a gap in the market for software engineering news with some exclusive stories, aka “scoops.” Was I observing things in the software engineering world that the mainstream media had missed, or was not interested in covering? It felt like that. So, in December 2021, I launched a new column called The Scoop, which published on Thursdays, irregularly.

Since the first issue went out, feedback has been very positive. The Scoop has so far heavily focused on how the hiring market is changing.

The Scoop has also started to feature “exclusive” news stories, as well. Although chasing “exclusives” was never my goal, thanks to my readers I’m getting an increasing number of tips about changes at tech companies that are relevant to software engineers.

This is how I was able to bring you exclusive stories like The longest outage at Atlassian, and How Fast rapidly collapsed - and what software engineers can learn from it, and The software engineer level changes at Netflix, and many others.

Writing The Scoop is pushing me to become somewhat of a journalist. I have no journalistic ‘training;’ I never wrote for a magazine, have had no form of education related to journalism, and had no intention of becoming a journalist. Still, much of what I write about in The Scoop involves talking to sources at tech companies, protecting their identities, collecting facts, and organizing those facts into a report. This newsletter has been the first to report on some unfolding stories, which journalists refer to as ‘breaking news.’

I’m navigating this new territory with the same ethos that I follow for the rest of the publication, writing the material I wish I’d had access to. I am as clear as I can be about where I get information from, I’ll sometimes share unconfirmed rumors if I find them interesting enough, and I don’t hide my own opinion about what I report. I take care to separate what is reporting on facts, what’s currently unconfirmed, what is analysis of information, and what is my own opinion.

If you see or hear something interesting as a software engineer or engineering manager, feel free to send me a tip here. Tips can be on changes at your company, or anything you’re seeing that’s relevant to tech professionals. I treat all messages as anonymous.

5. What I’ve learned about readers

A year into this, I’ve learned quite a bit about all of you, as readers. The below is a general summary of these observations. By nature, the statements aren’t true for all readers, they are just the trends I’ve noticed.

You enjoy reading about practical software engineering topics. Articles that have gotten above average positive feedback, include:

You love deep dives into engineering cultures. The two-part article on Facebook’s engineering culture and the one on Amazon’s engineering culture have not only gotten above average positive feedback, but a few engineers who joined these companies have shared how they used the articles as a guide to get more context and speed up their own onboarding.

You enjoy reading about Big Tech and career topics – every now and then. The below articles also received above average positive feedback:

Many of you love The Scoop – but not all of you. The Scoop, in general, gets positive feedback and most of you enjoy getting the “inside scoop” on what tech folks in the industry are talking about or focusing on. However, I do get regular complaints.

In 2021, most complaints came from hiring managers, telling me I focused too much on how hot the hiring market was. In the second half of 2022, most complaints come from software engineers telling me I focus too much on how worrying the hiring market is.

In both cases, the only way I could do anything about these complaints is to report less on what I actually see happening. I aim to provide a healthy balance of perspectives and news I’m hearing in The Scoop, and to organize issues thematically. However, my goal is to give you the pulse of Big Tech and startups. This pulse will not be representative of your reality all the time; it’s just additional information which I hope you’ll be able to utilize or discard, if not relevant.

6. What I’ve learned about the newsletter business

The Pragmatic Engineer is my main business and writing it is my new career. Reflecting on the past year, here are some business insights for those interested.

The paid newsletter model is a viable model for publications which mainstream media would never fund. I don’t have a background in writing or journalism. The topics in The Pragmatic Engineer are narrowed down to those that software engineers or engineering managers care about. When tech journalist Casey Newton – author of Platformer – and VC reporter Eric Newcomer – author of Newcomer – sat down to talk about newsletters, Casey said this about The Pragmatic Engineer:

“If you were to pitch [The Pragmatic Engineer] column to any mainstream publication they’d say, ‘that's way too niche, Hey, get out of here, our readers would hate this guy.’”

I never pitched the idea of this publication to any media company; I didn’t have any journalistic ambitions. And yet, both the numbers and the feedback show there is demand for coverage that – even if pitched – would likely be too niche for the mainstream media.

Nothing beats interesting, in-depth writing. The biggest spikes in subscribers – both free and paid – were when I published interesting, in-depth articles about a topic you couldn’t read about elsewhere. If it was a free article, it often gained popularity on social media. If it was a paid article, it got forwarded more than usual.

I have not engaged in any marketing opportunities or “growth hacking,” no bartering or other exchanges. I wrote no guest posts on other publications, except for cross-posting two articles to Newcomer – a tech VC focused publication – and Eric Newcomer also shared two relevant articles in return. My focus during the first year was to write about an interesting topic when I came across it.

This is how I decided to go deep into why JIRA went down for ten days for thousands of users without meaningful updates, or go broad and deep on the typical strategies of shipping to production.

Distribution channels still matter. I’ve not spent a single dollar on marketing or ads, and yet the newsletter grew dynamically. Where did people learn about the newsletter, and where did they sign up from?

For free subscribers, the traffic sources, in order are:

Substack Discover and Recommendations. The biggest way for new readers to find my publication is through Substack’s Recommendations system, launched in April. At the time of writing, 70% of new subscribers per month come from Recommendations and Discover, the majority through Recommendations. 65,000 of the 150,000 subscribers came from this source. My newsletter’s recommendations resulted in a comparable number of new subscriptions for other Substack newsletters.
The Pragmatic Engineer Blog. This drives about a fifth as many of the free signups as Substack’s platform features do. 15% of visitors coming from my blog signed up to the newsletter.
Twitter. I am a frequent user of Twitter, often sharing drafts of posts, as well. In August 2021, I had ~27,000 followers on the platform. This number grew to ~115,000 a year later. About 5% of visitors clicking through from Twitter became subscribers.
LinkedIn. Even though I post less frequently on LinkedIn, the platform drove only 10% fewer subscribers than Twitter has. About 8 in 100 visitors coming from LinkedIn signed up to the newsletter.
The Substack app. In what is impressive, the Substack iOS app accounted for almost half the subscribers who found me on LinkedIn.
Hacker News. While being on the Hacker News front page resulted in significant traffic: only about 1% of all visitors signed up for the newsletter, which is a much lower conversion than any other sources.
My YouTube channel. 10% of people clicking through signed up to the newsletter.

For paid subscribers, the channels they converted from, in order, are:

The Pragmatic Engineer Blog and Pragmaticengineer.com. By far the biggest channel for new paid folks.
Twitter. The social media channel driving the highest number of paid subscribers.
Substack Discover, Recommendations and the Substack app. Driving about half the number of paid subscribers as Twitter.
LinkedIn. Just below the number of subscribers who came from the Substack platform.
Google. In what is surprising, visitors finding the publication via Google ended up subscribing to the newsletter in similar numbers as all paid subscribers from LinkedIn.
Hacker News. A third of the number of paid subscribers who came via Google.

My engineering blog which I wrote for six years has been what’s helped the newsletter the most. Much of my credibility when starting the newsletter – and still the #1 source of paying subscribers – is my engineering blog. This is curious, as most Substack authors consistently mention Twitter as their main subscriber source – but it’s not true for me.

When I started writing my engineering blog in 2015, my goal was to write for myself, and I did not plan on monetizing it in any way. It would be four years later, in 2019, when I added a small ad unit to the blog to cover hosting costs, and in 2020 – just as I was leaving Uber – I added affiliate links.

I did not think my blog would play any role in any future venture. However, this blog was the playground where I got to practice writing, and also where many current newsletter subscribers first came across The Pragmatic Engineer.

Some of the most-read articles on this blog, all written before the newsletter was even a thought:

Choosing to host my own blog and own my own content was also a smart move. I use the hosted solution from Ghost. Ghost is very much customizable, so it was trivial to update my site to point to my new newsletter at the end of the articles.

Publishing an in-depth article every week means working on several articles in parallel. Many of my articles are a result of several weeks of writing and gathering feedback. While as a reader you see a new article every Tuesday, my reality is that I have several drafts at various stages of completion. Some have a table of contents, some are a first draft, some are getting content feedback, and a few are at the final stage of proofreading.

Most of the Tuesday articles take 2-3 weeks to finish from the initial idea, to a stage where they are ready to publish. Some of the really research-heavy articles can take up to two months: the Facebook one is a good example, which took even longer to finish.

At this point, I can’t imagine not writing this newsletter full-time. This is especially true since taking on The Scoop. Producing this news series also taught me something else.

I really like talking with people about stuff happening at their company and in the industry. I get lots of inbound messages on Twitter, LinkedIn and Signal, almost all from software engineers and engineering managers. I don’t just have these conversations to gather sources and information, but where I can – and it’s easy enough to do – I also offer my two cents on professional situations. I tend to get questions on negotiating packages, career progression, or requests for a second opinion on a situation in a large tech company, or a startup. You can reach out to me here.

While I don’t do mentoring, I do try to make time to give some feedback to questions where my perspective as an engineer or engineering manager could help.

7. Plans for the next year and a new holiday policy

The newsletter now comes out on Tuesdays and Thursdays, occasionally on Wednesdays. This is a change from a year ago, when I committed to publishing once a week. The schedule going forward, is:

Tuesdays: long-form educational / practical articles. These articles typically go deep into a topic relevant to software engineers or engineering managers, and offer actionable advice. One long-form article each month is for all newsletter subscribers.
Wednesdays: bonus articles, every now and then. In some cases, you might receive a bonus issue, every now and then. Bonus issues typically go out to all newsletter subscribers.
Thursdays: timely articles on Big Tech and high-growth startups. These issues are almost always The Scoop series, though I might add some pieces analyzing trends in future. Thursday articles are for paying subscribers; free subscribers occasionally get one of the several stories covered in The Scoop.

For the next year, here are things I’m planning.

More engineering culture deep dives. Expect more on Big Tech companies and some interesting high-growth startups being covered in similar depth to what you’ve read about Facebook and Amazon. If you work at Microsoft, Apple, or Stripe as a software engineer or engineering manager, I’d especially love to hear from you.

Practical software engineering topics – some from guest writers. You love reading about topics close to software engineering. With a backlog of interesting topics to cover, expect more of these. Expect to see more industry experts covering some of these topics as guest writers. For example, next week, former Facebook data engineer Ben Rogojan, aka SeattleDataGuy, will share the essentials that software engineers should know about data engineering.

Branching out into areas related to software engineering like data, machine learning (ML), security, and more. Although the newsletter is focused on software engineering, there are emerging areas to cover like data engineering, ML engineering, security engineering and also newer roles to investigate, like solutions engineer, cloud engineer and many others.

What connects all these areas is how software engineers can – and sometimes do! – transition to and from these areas. Engineering managers also sometimes find themselves managing these teams.

In year 2 of the newsletter, expect to occasionally read about these areas, via experienced individual contributors, or managers working in these disciplines.

Experimenting with new, additional columns. I love testing new ideas, and in the last year you’ve seen some of them. Experimentation is table stakes when you work at any fast-moving startup – like most places I worked at were during the past decade – and it’s also a lot of fun to try out new things. At the same time, I’m keeping tabs on these experiments, retiring those that don’t work, and doubling down on the ones that do.

Real World Engineering Challenges was an experiment that I initially got mixed feedback on, and so put the series on hold. After gathering extra feedback and thinking more about it, the series is back. I plan to integrate the concept of a broader “what is interesting in the industry” article into the publishing schedule, once a month or so. This series is deliberately much less deep than other articles, but it’s more broad and points to resources so you can dive further, if you’d like to learn more.

Community Threads were a very mixed bag and polarizing. Some people loved them, some people hated them; thank you for all the feedback! I’m putting Community Threads on hold for now. I do like the idea of having more input from subscribers, but this format did not work so well.

Keep on keeping on. The Tuesday deep-dive articles and The Scoop are both here to stay. My goal is to keep the quality as it is, and to have a healthy mix of topics relevant for software engineers, engineering managers, those at Big Tech and people at high-growth – but possibly not so big – startups.

A holiday policy. During the first year of the newsletter I did not take holidays. Well, I did go on holiday trips for which I aimed to work ahead, but in the end I never went a day or two without writing, even on vacation.

Going forward, I’ll now – finally! – have a holiday policy:

No newsletter issues during the last week of the year. Between 24th - 31st December, there will be no newsletter articles.
Only one issue a week instead of the usual 2, during 4 weeks of the year. I’ll be taking 4 weeks of holiday per year when I don’t write at all, including not writing The Scoop articles. Tuesdays’ long-form issues will still go out during these weeks, except for the last week of the year. I’ll give you a heads up when The Scoop is about to pause.

I’m very excited for the second year of The Pragmatic Engineer newsletter! Thank you for all the support during the publication’s first year. I’m diving into this second year with energy and enthusiasm. I’ll keep writing about interesting, educational and timely topics for those working in tech, with an ongoing focus on software engineers, engineering managers and those in Big Tech and at fast-growing startups.

Here’s to another great year!

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In The Pragmatic Engineer, I cover challenges at big tech and high-growth startups through the lens of engineering managers and senior engineers. Subscribe to get this newsletter every week 👇

Sergio Rodriguez

Sep 7, 2022

Congratulations on your first year! Keep up the good work and looking forward to the next phase, especially learning about related areas like ML and Infosec.

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