The Pragmatic Engineer: Five years

Wow, has it already been five years?! The newsletter hits a big milestone this week, and it wouldn’t have been possible without subscribers. Thanks to everyone who’s read an article or listened to a podcast episode during that time!

Before we get into the latest issue, I’d like to point you to two upcoming events in New York City which I’ll be at. It would be great to meet some of you! They’re free to attend:

• Wednesday, 16 September, 6pm: turbopuffer talks. What happens when you mix a whiteboard, two senior turbopuffer engineers, and myself, with the spotlight on database internals? We’ll draw out turbopuffer’s database architecture and geek out over it, then hang out afterwards. Join us! Sign up here.

• Thursday, 17 September, 5:30pm: An evening with The Pragmatic Engineer and WorkOS. A fireside chat between WorkOS founder, Michael Grinich, and me, with him asking the questions. We’ll get into stories about the tech industry – including a few which probably won’t get published! Sign up here.

If you’re at LDX3 New York on 15-16 September (Tue & Wed), I’ll be doing a keynote on Tuesday morning and hanging out around the Antithesis booth during the day. See the full agenda and get tickets.

I checked the calendar and it is indeed half a decade – almost to the day in 2021 – since I published the first-ever issue of The Pragmatic Engineer:

On launch, the paid version of The Pragmatic Engineer cost $100/year, or $10/month (this has since increased to $150/year or $15/month). As a special offer, I’m “resetting” the price of the publication to annual subscribers for $100/year: claim this offer here. The offer ends in a week, on 8 September. Get this offer here.

My personal expectations weren’t high back then; the subscription model for newsletters on platforms like Substack was starting to take off, but the focus was strongly on politics, business, and finance. It wasn’t clear if there was any demand for a publication about software engineering, written by a software engineer.

I soon found out there was demand that surpassed all my expectations – and then some! Fast forward to today; the newsletter has more than 1.1M readers, tens of thousands of paid subscribers, a podcast, and more than 500,000 YouTube subscribers.

But the numbers aren’t the most validating thing for me; that would be the feedback sent in by readers. Via email, in DMs, or in-person at events, it’s great to hear how an article or a podcast we published helped someone try a new approach, or to gain confidence that theirs was the right one, or that an article helped convince a team to change things. It also means a lot to learn that The Pragmatic Engineer helps people feel more confident about keeping up in this fast-changing industry.

Thanks again for your support! It’s the reason why The Pragmatic Engineer is a viable business and a growing publication, and means we can “scale up” our coverage to deliver ever-more detail about how software gets built, today.

Today’s issue covers:

1. Diving deeper, year after year. The evolution of the Pragmatic Engineer’s coverage over five years, getting in through the “front door” instead of the “back door” for deepdives, launching the podcast, The Pragmatic Summit, and growing our team.

2. What’s next? What we’re excited about, the second Pragmatic Summit, and how you can expect us to stay focused on how building software is changing, and the ways that successful engineers, teams, and companies adapt.

3. Cash-prize writing contest: Software is changing faster than ever. Send us your essay about how things are changing for you, for the chance to win cash prizes worth up to $10,000. Read more on how to take part.

1. Diving deeper, year after year

The Pragmatic Engineer was 15 years in the making and not an overnight success; I started to write a blog in 2007 about software development, which was “rebooted” as “The Pragmatic Engineer Blog” in 2015. At the time, it was read by almost nobody! In 2019, I launched an email digest (“v0” of the newsletter), and a year later, I decided to focus on the newsletter fulltime after quitting Uber as a manager following job cuts in 2020, when a quarter of my team was laid off and the rest were disbanded due to the pandemic. I took an employment break, planning to finish ‘The Software Engineer’s Guidebook’ in six months and then start a VC-funded startup. In the end, finishing the book took another two years, and I didn’t kick off that VC-funded startup! Instead, I decided to go all-in on writing a newsletter targeted exclusively at software engineers and engineering leaders.

2021: product-market fit

The Pragmatic Engineer started off with one in-depth article on an interesting topic per week, including these ones:

• The Platform and Program Split at Uber: platform teams were starting to go “mainstream” across the industry

• How Big Tech runs tech projects and the curious absence of Scrum: this article made a splash

• The perfect storm causing an insane tech hiring market: the job market in late 2021 was one of the hottest ever seen