Amazing 3 Years of Writing the Engineering Leadership Newsletter 🥳 🎉

Overview of the 3-year journey and goal for the newsletter in the future!

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This week’s newsletter is sponsored by DX.

How 18 Top Companies Measure AI’s Impact on Engineering

Written by Laura Tacho, CTO at DX, this new industry report explores how 18 engineering organizations—including Dropbox, Microsoft, GitHub, Atlassian, Adyen, Booking.com, and Grammarly—are measuring AI’s impact on software development.

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• Common patterns: Why most companies track speed, quality, and maintainability alongside AI usage.

• Unique metrics: A deep dive on Microsoft’s “Bad Developer Days” and Glassdoor’s experimentation measures.

• Practical guidance: How to get started with the AI Measurement Framework and guidance for collecting metrics.

Thanks to DX for sponsoring this newsletter, let’s get back to this week’s thought!

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Intro

I recently had the pleasure of attending a local meetup, where I shared my 3-year journey with writing online. I had a great time there, and it was great to meet and chat with everyone.

Here are also some of the pictures:

In the current fast-paced world, we rarely take a moment just to realize where we were and where we are right now. So, when I was preparing for the presentation, it felt nostalgic thinking about the 3-year journey.

It’s been an awesome journey so far, and I am really happy to have started it 3 years ago.

Today’s article is a special “3-year anniversary” edition, where I am sharing my 3-year journey of writing online with the focus on the last 1 year!

Visual/Audio Version of the Article

You can watch/listen to the video below, or you can keep reading for the complete overview and insights of today’s topic!

Let me first start with sharing some interesting statistics of the past 3 years of writing the newsletter.

Interesting Statistics of the Past 3 Years of Writing the Newsletter

• 208 articles (today’s included) → at least 1 article per week. The last 1 year → 2 articles per week.

• 28 guides, templates, and infographics, 4 new added today:

  • Notion Template: AI Communication Cheat Sheet

  • Infographic: Traits For Engineer’s Career Success

  • Infographic: How to Be Productive

  • Infographic: How to Be a Reliable Engineer

• 312k~ words written (about 1500 on average per article, older articles were less, but currently I am aiming for 2000+ per article) - Average engineering book word count is about 60-70k, which is around 5 books!

• 165k subscribers

• 1504 paid subscribers

• Readers from 195 countries

• 10,588,562 (10.6M) views → Apart from direct email opens, the biggest sources have been:

  • Substack

  • Reddit

  • LinkedIn

  • Google

  • Daily.dev

  • HackerNews

  • X

  • GitHub

• Longest article: How to Use AI to Be a Great Engineering Leader

  • 30,075 characters

  • 4,933 words

  • 22M 25S ~ reading time

  • 32M 53S ~ speaking time

• Most viewed article: Context-switching - one of the worst productivity killers in the engineering industry

  • 81,668 views

  • 246 shares

• Most shared article: 200+ Resources to Become a Great Engineering Leader in 2025

  • 71,878 views

  • 264 shares

Now, let’s get more into the progression over the 3 years of writing the newsletter.

Starting the Newsletter + First 2 Years

You can read the full insights on how I started the newsletter + my progression over the first 2 years here:

It’s been amazing 2 years of writing the Engineering Leadership newsletter 🥳 🎉

Here is a quick TLDR:

• How I picked the topic

There weren’t a lot of engineering leadership resources when I first grew from Senior Software Engineer to Team Lead. I made a lot of mistakes and was struggling with the transition.

After many mistakes and some wins, I started to get the hang of it. But if I had resources like the ones that I am writing, the transition would be much easier.

And that is the goal → help as many engineers and managers to become great engineering leaders.

A lot of articles are written in a way that my past self would get a lot of value from!

• 0 - 6 months (0 - 200~ subscribers)

I was just sending out the newsletter, and that’s it. I didn’t really take the time to promote it and make it visible. But I kept being consistent and persevered.

• 6 - 12 months (200 - 15.000 subscribers)

I started building good relationships with people who are on a similar path to me. We have supported and helped each other. This has substantially helped all of us to progress and learn faster.

I moved from being a lone wolf → to a collaborator and being helpful to others around me.

I started to also post daily on LinkedIn, which has helped me increase the reach and visibility of the newsletter as well.

• 12 - 18 months (15.000 - 50.000 subscribers)

This was the stage where I saw amazing growth, which confirmed that I was onto something here and gave me the confidence to keep moving forward and progressing + keep making things better and better.

• 18 - 24 months (50.000 - 77.000 subscribers)

I started to really get a hang of the process and my writing style + have built the consistency that I have confidence that will never go away.

I have been truly enjoying writing, and it’s something I see doing for a VERY long time.

From Year 2 to 3 (today)

Now, let’s focus on how things are going from year 2 to today.

As I have mentioned in the 2-year anniversary article, I have started with 2 articles per week. Paid newsletter article on Wednesday and an article for everyone on Sunday.

I’ve been continuously sending them out for the past year, and well… It’s been one of the best decisions I’ve made!

Here is why:

We’ve been able to grow from around 77k subscribers to 165k, which is a 2.14x increase.

We’ve been able to grow from 628 paid subscribers to 1504, which is a 2.39x increase.

And we’ve been able to grow from 43.3k ARR (Annual recurring revenue) to 121.3k, which is a 2.8x increase.

Now, that all sounds great and it’s really awesome and I’m REALLY proud of it, but let’s get into the real world.

The Announcement

When I announced that I will be focusing more on the newsletter, I wanted to seem confident, because I knew that if I wanted it to work out, I needed to inspire trust in people.

I did the announcement on LinkedIn, a separate email to all the subscribers, and of course, I also wrote my full reasoning in the article: It’s been amazing 2 years of writing the Engineering Leadership newsletter.

But the truth is that I was quite nervous about it at that time.

I knew I could handle the additional article per week → I wasn’t worried about consistency, as I have built that up through the last 2 years of writing.

But I think there’s just something deeply rooted inside us as engineers / engineering leaders of that feeling of selling something.

I think many people can relate with it → That feeling of trying to sell something and at the same time thinking “is it actually good enough” and “what will everyone think” if you try to charge for your work is very real.

Even though I did a LOT of freelance work over the course of my career, I never tried to sell a product on the scale I am doing it right now.

And I felt that heavily at that time, but what’s interesting is that nothing really bad happened :) Only amazingly good things!

So, if you are in a similar boat, feeling anxiety of trying to sell something, just go for it → it will not be easy, but extremely worth it when you do it. And even if you don’t get the results you want, it’s going to get easier and easier to do it over time. That is the biggest benefit IMO.

And the thing is that with everything we do both in life and in our careers, we are all selling something all the time. Our knowledge, competence, getting a buy-in on a certain project, idea, suggestion, etc.

So, becoming better at it is only going to be a big upside.

Now, let’s get to the second thing I have focused on when I started with the additional newsletter article per week.

Improving the Quality of Articles and Overall Usefulness

You might have noticed, over the course of 3 years, the way I write and what kind of articles I create → I try to improve them continuously.

And I deliberately decided at the 2-year mark that I will focus on increasing both the length of the articles and also how they are written + overall usefulness.

So, not just adding an additional article per week, but trying to make them better as well. And that is going to be my continuous goal, I’ll be striving toward → how can I keep making my articles better and better over time.

So, the main guidelines for every article I have now are:

• The article is 10+ min read, which is about 2000 words

• It’s better to write from experience and share examples than just theory → this is VERY important, as I am a huge believer of sharing actual experience being the most interesting thing

• 3+ visuals per article, I normally do more

The process for creating articles is still the same as I had before. I am a heavy user of Notion, and I have more than 1000 ideas for new articles in there.

I am also constantly speaking with engineers and managers, and checking what’s happening across the industry → reports, statistics, trends, etc. That’s how I spot the issue of 51% of engineering leaders perceiving AI negatively, which was caused by sensational takes and FOMO.

And also, the outcome of speaking with many people has been these 2 articles, where I gathered the insights of professionals from all kinds of companies to share their insights:

• How to Use AI to Increase Software Development Productivity

• How to Use AI to Be a Great Engineering Leader

Plus, many collaborative articles with amazing professionals spanning various roles and industries.

I’ll keep mixing my own insights with the insights from other professionals. I strongly believe that’s how you, as a reader, get the most value.

This Has Been a First Year Without a Full-Time Role

As you may already know, and I have shared this on many occasions, in my full-time career, I grew from an engineer all the way to CTO.

After being a full-time CTO for 2 years, last year in October, the company I was with didn’t work the way we had planned it out, and we needed to stop pursuing the product-market fit and disband the company.

So, that was the time I decided not to pursue another full-time role and focus a lot more on the newsletter, course, and also fractional work and coaching.

The Biggest Challenge for Me Has Been Prioritising What to Focus On

When you can do SO many things and there are many opportunities that you can focus on, you find it hard to see what’s really worth it and what’s not.

There are literally a million things you can spend your time on: from doing videos, projects, writing articles, posts, coaching, consulting, etc.

And I also received many opportunities spanning from:

• full-time roles + various part-time roles,

• co-founding startups,

• projects.

That’s when I decided I will prioritize things based on this perspective:

What’s going to be the best for the newsletter and what will make me a better engineering leader.

The goal for me is to be the best engineering leader I can and help the most people possible along the way I can.

So everything that is aligned with:

• How can I improve the most

  • By getting to know as many different perspectives and challenges + help solve them (here are the options to work with me)

• How can I help the most people

  • Writing more relevant and useful things, reaching more and more people

That is my focus, priority, and vision for myself. Everything else comes after.

I may do a more thorough overview of moving from a full-time job to full-time entrepreneurship in a separate article. Let me know if that’s something you’d like to read.

My Goal is to Make This Newsletter the Go-To Resource for Engineers and Managers

Now, let’s talk about what the goal is.

As part of my perspective and focus, my biggest focus moving forward is going to be how I can make this newsletter the go-to resource for engineers and managers for becoming great engineering leaders.

I will keep looking for ways to improve the articles, add resources, write about more relevant and useful things, and continue experimenting with videos + other initiatives.

I am always looking for great people who can support me along the way as well. I am working with some awesome people (on a fractional basis) who help me with: admin, video editing, accounting, design (infographics), SEO, copywriting/editing.

What really drives and motivates me is that I know there is no finish line at the end.

This is something I can continuously work on, progress, improve over time, and also, most importantly, help as many people as possible along the way!

Thank you for Your Continuous Support Over the Last 3 Years 🙏

I have many exciting topics lined up for the future and can’t wait to share them with you! If you are not a paid subscriber already → to not miss out on any of them in the future, you can become a paid subscriber here: Become a paid subscriber.

Last Words

It’s been an awesome 3-year journey of writing online, and I am excited to see what the future will bring. Thanks again for your support. I’ve learned a LOT throughout the journey, and it’s been one of the best decisions I have made.

The only regret? Not starting with it sooner!

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Get in touch

You can find me on LinkedIn, X, YouTube, Bluesky, Instagram or Threads.

If you wish to make a request on particular topic you would like to read, you can send me an email to info@gregorojstersek.com.

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