8 months ago, I quit my director of engineering job to take an 8-month break.
The time is up.
It has been… Different. Yeah, I think different captures it. I’ve felt at times uncertain, confident, exhausted, relaxed, anxious, and free. And manager.dev has been at the center of it.
Today’s I’ll share:
A TLDR for those just mildly curious
What’s next for manager.dev
A deeper dive into my experiences (and job searching)
TLDR
Here’s how I defined my goal after I quit:
Take time to explore and figure out what I REALLY want. What’s more important for me:
Stability or risk?
9-5 or freedom?
Family time or ambition?
Tons of money or enough-but-less money?
Making an impact on the world or doing what’s convenient to me?
Here’s the TLDR:
I tried building indie products, doing courses, sponsoring out my newsletter, and starting a startup.
It was harder than I expected.
I learned a lot about myself. I prefer stability to risk, a comfortable 9-5 to scary freedom, family time over ambition, and convenience over impact.
I don’t think I would like to be a CEO, or even an entrepreneur.
I started last week as an Engineering Management Evangelist at Weave (which I’m very excited about)!
And, I’ll be back to a full-time Engineering Management role in a month (more details soon!)
Keep reading if you want juicier details :)
What’s next for manager.dev
I started this newsletter more than 2 years ago, after some conversations with and . I definitely didn’t think I would enjoy it enough to publish 100 articles and get to >23k subscribers!
My goal was simple - there is a lot of content for engineers and for CTOs. There is not enough dedicated solely to first-line engineering managers, which imo is the hardest job in tech.
Slowly, I got better. My average article reaches 13-14k+ EMs, and some even went crazy viral.
During my break, I needed to find a way to generate money. I thought A LOT about creating a paid subscription tier, locking the archive, and having premium articles. I know that if I do that, I’ll be able to get to $15-20K ARR in a few months.
Every time I was close to doing it, I remembered my initial goal. I’m going for the longer term here. My role models are not Ben Thompson, Lenny and Gergely Orosz - they are Will Larson, Jeff Atwood, Joel Spolsky, and .
I want to write for YEARS, as I progress throughout my career. I want to share my learnings in real time. I don’t want to depend on my writing for income, and to optimize for ARR. Nothing bad with that - I just feel it’s not for me.
If I do a paid subscription, it will be with perks other than the articles.
Sponsorships
I started experimenting with sponsors. After some initial mistakes, I set the bar high, and said no to quite a few. I want to share products that are actually good, that I understand, and that are relevant to EMs.
My goal is to get Linear for a long-term sponsorship :)
Online course
I also launched a course in Maven, called “Hacking Engineering Management: Achieving Bigger Impact Where It Counts”. The first cohort got amazing reviews, and I’m organizing another cohort next month (With the REALREADERS code, you get 35% off, the cheapest the course will be. could not skip the chance to promote it 🙃).
manager.dev site
I had big dreams for this site, and I will share them in the next section. Currently, it’s a bit dead, with just the results of the survey available (700+ EMs filled it!). There is also an app for EMs I’m working on - it started off just something for the course participants, but I got good feedback and I may turn it into something bigger later.
So my plan is:
Continue with free weekly/bi-weekly articles
Try to get high-quality sponsorships
Do courses for EMs. The one currently running is about creating impact as an EM. Some additional course ideas I had:
Engineer→EM
Just promoted EMs
EM→Director
Invest the money back into the business.
How can you help (if you want, of course)
I have many ideas I would like to pursue. The app for EMs, a podcast, illustrations for the content, an all-time archive of EM-relevant articles from across the internet, games, and more.
Once I start to earn more money, I plan to hire people to help me with some of those.
If you would like to help, I have a buy-me-a-book link (I don’t like coffee, but I REALLY like books 🙃). The money will go back to the business, and you’ll support free knowledge for the next generation of EMs! :)
Also - a great and free way to help is to give a try to the products I sponsor! My best sponsor is currently unblocked, and they have a great product that helps engineers save tons of time, and I recommend booking a demo! (this one is not sponsored 😂). If companies have good ROI with my newsletter, I’ll be able to attract quality ones for repeated appearances and raise prices. On my side, I promise not to sponsor shitty or irrelevant products.
Next is the personal and longer part, thanks for reading :)
How my ‘break’ looked like
In all honesty, it was not what I expected, and not in a good way.
Here’s the breakdown:
February
During January, I already started working with a couple of friends on a product aimed at first-time parents, called Kiddo. An app to help you develop your child, and spend better quality time (with activity ideas, progression of skills, and other cool features).
By the end of February, the MVP was done, but it just didn’t feel right. There were 2 main problems:
Parents who wanted ideas and tracking already had ChatGPT, and we didn’t provide something unique enough.
The team wasn’t right, and I didn’t enjoy working with them.
I guess the 2nd bullet point is the critical one.
Anyway, I decided there was no sense in continuing with Kiddo.
March
Next came something I wanted to do for a while. I already had a big audience here and on LinkedIn, and many people advised me to do something to monetize it.
My thought process went like this:
Buy a cool domain (thanks for the manager.dev name idea).
Organize all the best EM-related articles from across the internet. I felt that with ChatGPT and all the social networks, there were tons of ‘ok’ knowledge and articles, but nobody knew where to find the true masterpieces - some of them were written 20 years ago!
Move my own articles to the website as an additional way to get traffic (50-100k views a month).
Create a survey where EMs will share their current situtation.
Based on the survey, my own content, and the ‘masterpiece’ articles, create a personalized email course. I already launched a $59 email course the year before, which 15 people bought, so I felt there was a market. Basically, you will get super high-quality content tailored to your situtation and challenges.
And then I’ll have a funnel - articles→website→survey→course.
I was pretty excited about it. In March, I bought the domain, created the basic website, finished the survey functionality (and published it), and also created the infrastructure for the personalized course.
April
And then came April. It started with Dan (my son, 2y old) getting Sick for a week, so I stayed home with him. Then, there were holidays (no kindergarten), and my wife was abroad. Then he got sick again for a week.
Since the end of January, I was the one spending the most time with him (until 8 am and from 4 pm till night), but full days were much harder than I expected… Kudos to all the full-time parents!
Anyway, during that month, I lost momentum. When I had some time in the evenings, I just read books, and didn’t have energy for anything else.
I started to doubt whether my idea would make money, and I also started to miss full-time employment. It was quite lonely and stressful (for me at least) to work without a team and to make all the decisions myself.
Then came 2 great offers:
May
was planning to launch the 4th cohort of his course for EMs, and offered me to join. I participated in his 3rd and really loved it.
A friend got some traction for a product he was building in the BI and data space, and it looked like there was real potential for a startup there.
So in May, I decided to put the manager.dev project on hold.
Course
I joined Gilad in instructing his course (we had 10 participants, which was great for a $1000 course!). I enjoyed it, but felt that I wanted to be the one leading it, which led me to launch my own course 3 months later.
Wizbi
I also started to work on Wizbi. It’s an agent that understands your BigQuery data warehouse, and you can ask it questions via Slack/web/Whatsapp, save results in graphs, and do some other cool things.
I won’t go too deep here, but we felt there were some things we did uniquely, and there was a market for this product.
June
In June, it was full building time. I think in May+June it was ~250 hours, ~60k lines of code, some integrations, and a working (and demoable) product. We had more ideas, but it was time to start selling.
And here’s where shit hit the fan.
July
Our goal was to get as many customers as we could into private beta by the end of the month. Our ICP was 100-500-person companies that use GCP and BigQuery, and already have BI analysts.
Let me tell you - selling is fucking hard! Neither of us had any experience in it.
Slowly, we improved. We got better at handling objections, and showing why we are unique. We had some positive signs, but the process was very long - we had to go through many stakeholders in the company.
And in 2025, with the amount of new tools that pop up everyday, most companies were reluctant to try something new, even if it solved an important problem.
August
We reached the beginning of August, and my willpower broke.
I knew that what we were going through was a part of building a startup. I knew that we could push through, improve our product and offering, niche down, and get our first paying customers.
But, I also felt that it wasn’t for me. That I was not built for it. I missed working with a strong team of engineers, and I missed NOT being a founder - having someone else deal with the big headaches.
There are so many advantages in a classic EM role that I didn’t appreciate until I left.
And in addition to all that, my wife and I are expecting a 2nd child, which added to the financial responsibility I felt. When we planned this break, we planned for 8 months - meaning the end of September, and it was coming soon.
So, I broke down the bad news to my partner. I tried to help him in the transition, as he is planning to follow through (which I think he should - he’s much better built for this!), but it was still a tough breakup.
Lucky for me, the next part went very well:
I had 3 roles I wanted - 2 as EMs and 1 as VP R&D in a pre-series A startup. I passed all interviews for 2 of them, and went with my gut, taking the EM role, which I’ll start on October 19th. From the first interview to signing up, it took just 2 weeks (and 13 interviews across the 3 companies), which I’m very grateful for.
September
I really planned to relax in September-October. Honestly.
But at the end of August, Adam from Weave (YC W25) reached out to me. We’ve been in contact for a few months, and I really love their product and mission - sharing the truth about what happens in engineering.
I agreed to join as an Engineering Management Evangelist - I believe the first role of that kind.
It’ll be a combination of Engineering, Writing, and Marketing. You are going to hear more about them soon :)
Wrapping up
My goal was achieved. I learned about what I need, and what I’m not built for:
I spent a lot of time with my son, and understood I’m not willing to sacrifice family time for a grueling startup journey.
I need someone to be in charge, and that’s ok.
I thrive in certainty and stability, not chaos.
I like to work with people and bigger teams. Working solo for days and months was mentally hard for me.
In total, I earned a total of $20K across those 8 months (which is not a trivial amount, but also not something I could live off).
I’ll wrap up with the quote I used in the original article:
I’m making my own trail. That 8-month break was an amazing decision.
I’m going back to a full-time EM job, excited and without any regrets. I will continue to build and write for EMs on the side, and also advise and work with great startups I believe in.
I feel grateful for the opportunity I got, for the family I have, and for the privileges in my life.
Discover Weekly
Thought Experiment - Mental Model: What If? by . If you are considering taking a break, or doing a change, use this super useful mental model. It helped me understand that the upside of quitting was much higher than any downside. The worst-case scenario happened - and here I am, a bit poorer in money but much better set for the future.
No Pain, No Gain - on firing people and other challenges of EMs by .
Programming Deflation by . A short and intriguing piece on the future of programming.
