Lessons From 4 Years of Writing the Engineering Leadership Newsletter

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Intro

2 days ago was 4 years since I first started writing this newsletter! On October 3, 2022, I published my , which was an announcement that I was starting a newsletter.

And as every year, it’s now a practice to create an “anniversary” newsletter. So, this year, it’s no different :)

If you want to read the 2-year and 3-year anniversary editions, you can do so here:

For today’s article, I’ll be sharing a bit about my beginnings, the most important lessons I learned from 4 years of writing, and what I would tell myself 4 years ago.

Let’s start!

If you haven’t built your own blog, are you really an engineer?

Joke aside, I remember when I first started writing 4 years ago and published my first article, or, more accurately, blog post. Back then, it really was a blog that I built myself with no AI tools, of course :)

It looked like this:

It was built with React + Gatsby, and I had it hosted on Netlify.

At the same time, I also created this newsletter, as you know it today, but it was more just for sending emails, and the blog was used as a primary source.

Back then, there were, of course, no AI tools, as we know them today, so maintaining and building your own blog took away some of the precious free time that I could spend writing. I also worked full-time as Head of Engineering at that time.

So, after about 6 months to a year, I decided to stop supporting the blog that I coded myself, and focused on continuously improving my writing as much as I can.

What started as me sharing my experience and what I have learned throughout has now become one of the biggest and most-read platforms for engineers and managers.

With over 10M views in the past year, this newsletter is the #1 recommended newsletter for engineering leaders based on various sources and, of course, different AI tools.

I am honored and thankful to everyone who is reading! And I can’t thank you enough for the continuous support over the course of 4 years of writing.

To show just a bit of my gratitude, I’ve mentioned the great Engineering Leadership newsletter community in the acknowledgments section of , which is coming out soon!

I shared the following:

Special thanks to the Engineering Leadership newsletter community. What started as me sharing what I had learned throughout my career grew into a community of 200k+ engineers and leaders from around the world. Your replies, questions, disagreements, stories, and feedback have helped me tremendously to think more deeply about engineering leadership. Many ideas in this book became a lot clearer because I had the opportunity to explore and discuss them with you.

Let me share, next, my most important lessons I learned through 4 years of writing this newsletter.

My most important lessons from 4 years of writing

• Consistency beats almost everything

I’ve created over in the span of 4 years, and never missed a week. For the first 2.5 years, I was doing 1 article per week, and for the last 1.5 years, 2 articles.

Even though not every week I was happy with the article (still not), it went out, I’ve kept publishing, and if you’d asked me 4 years ago that this newsletter would become the go-to resource for engineering leaders, I wouldn’t believe it.

And of course, other things have always come up, like life, or especially for the last year, writing the book and managing all the other things, you find yourself having less time, but it’s really important to have some non-negotiable things you want to do no matter what else happens. It keeps you focused on your goal.

As I mentioned in one of the past articles, I like to have daily and weekly goals. Daily goals are specific to the day and may be like: publish a post on LinkedIn, exercise, or attend a certain event.

And for weekly goals, it may be publishing 2 articles, publishing X amount of LI posts, etc. This keeps you focused on what are the important things you need to do, without feeling the pressure from having a lot of things on your mind. That has worked really well for me over the last 4 years.

• Writing is thinking and learning

Now, this is especially important to understand today, with so much AI-generated text everywhere. I look at writing as thinking and learning. When I write about something, I need to understand it first, only after I can write well around that topic.

So, if you just generate text with AI, you are missing out on the important learning.

Even with all the interviews I do, for example with , or with , I focus on understanding what they have said, and then write about that specific part in the style that I normally write.

That enables me to learn and really understand things, and whenever I need them, I can quickly remember where something was mentioned and can re-read it.

It’s also the reason that whenever I talk about a certain topic, either give a talk at a conference or have a conversation with someone, I can quickly connect my learnings to something that I am talking about.

And especially when I give a talk and I get “in the zone”, I can talk about engineering leadership topics forever, without needing to prepare a lot beforehand.

So, if you try to “shortcut” your way to the end result, unfortunately, you are cheating yourself with that, and you are losing out on important learnings, which has actually been your goal in the first place with writing. To learn, understand, and share your knowledge with others.

• The newsletter became bigger than the newsletter

As mentioned, 4 years ago, I wouldn’t have believed all the opportunities that would come if I started sharing my thoughts online. I had the pleasure of giving a talk or hosting a workshop at 12+ conferences over the course of a bit more than 2 years. I was also a part of 30+ podcasts, webinars, or similar.

Earlier this year, I also hosted my first event called . There were close to 200 people attending, and it was a blast. Looking forward to doing more such events in the future!

And then, writing the book The Multiplier Mindset, which I started in December, 2025, has been a big goal of mine that I wanted to do for quite a while. I was thinking of doing self-publishing at first, but after speaking with O’Reilly, I knew I made the right choice going with them.

The book is much better, the core message is so much clearer, and I couldn’t be happier with the outcome. I’ll write about the whole process of writing the book in one of the future articles, so stay tuned for that!

And not to mention all the other opportunities like consulting, coaching, and full-time role opportunities. They all came because I started sharing my thoughts publicly.

• The biggest lesson is the impact of creating something useful for a long enough time

My main goal is and always will be to make everyone to be a better engineering leader. With every article I write, every template I create, or every talk I give, that’s always the focus.

And I believe that has been one of the key things for the success of this newsletter in the past 4 years. A lot of people are telling me that they really like the actionable advice that they can use immediately, and that has been my goal.

And the same goal is with the book The Multiplier Mindset. I focused on making every page to be as actionable and useful as possible, something that can help you be successful.

And I fully believe that if you read the book or my articles and apply them in your own case, your success is inevitable.

When I asked people for feedback and reviews of the book, I was surprised they mentioned the newsletter as well. Here are 2 pieces of feedback that connect to the newsletter:

“I've read Gregor's newsletter for nearly two years, and his advice is always practical and battle-tested. As AI writes more of the code, this book is his playbook for what matters more than ever: multiplying the people around you.”

“I've been reading Gregor's teachings since his newsletter first started out. They are valuable because they're rooted in practice and always hands-on. This book distills the best of them into one playbook for engineers growing into leadership.”

So, what I want to mention here is the importance of creating something useful (or being useful) and sticking to it for a long enough time.

This can be anything, it doesn’t need to be a newsletter, it can be anything else.

The same exact mentality you can use for growing in your career as an engineer and engineering leader. Being useful, and doing great work + making sure that your work is visible for a long enough time and stick to it. That’s how you grow and progress.

What I would tell myself 4 years ago

The biggest regret I have regarding the newsletter is not starting it sooner. So, if I could go back in time even 2 or 3 years before I started, this would be my go-to advice: Start writing asap.

And this would be my exact words:

Start before you feel ready. Don’t worry too much about the platform, subscriber count, or whether every article is perfect.Focus on creating something genuinely useful, keep improving, and give it enough time to compound.

Additionally, I’d mention a really important thought that I know is holding back many people from trying something new:

Stop worrying about what others would think. Everyone has their own problems to worry about, so they are not too concerned with what you are doing.

I spent too much time thinking about “what would everyone think if I post this article or this LinkedIn post”, my colleagues, friends, family, etc.

But then only good things have happened when I openly started sharing things.

I’ve broken this down fully in this LinkedIn post:

And you can read more about the Spotlight effect in this article:

Last words

Thanks again for your continuous support. I’ve got a lot of great things coming up for the newsletter, including an upcoming book launch! I am really excited for that, and I’ll let you know once the book is published!

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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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You are more than welcome to find whatever interests you here and try it out in your particular case. Let me know how it went! Topics are normally about all things engineering related, leadership, management, developing scalable products, building teams etc.