Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer)
Lenny interviews Gergay Oroz, the creator of The Pragmatic Engineer, Substack's top engineering newsletter. They discuss Gergay's journey from a high-paying Uber job to full-time newsletter writing, the pros and cons of this creator life, and actionable advice for aspiring writers and entrepreneurs.
Deep Dive Analysis
13 Topic Outline
Gergely's Career Journey to Full-Time Newsletter Writing
Growth and Scale of The Pragmatic Engineer Newsletter
Compensation Comparison: Newsletter vs. Uber Salary
Decision to Leave Uber and Pursue Writing
Daily Life and Cadence of a Full-Time Newsletter Writer
Strategies for Productivity and Maintaining Focus
Favorite Aspects of Entrepreneurship and Solo Work
Unexpected Downsides of Solo Newsletter Work
Long-Term Vision and Adapting to Opportunities
How The Pragmatic Engineer Gained First Subscribers
Advice for Aspiring Newsletter Writers and Creators
The Importance of Depth and Credibility in Content
Leveraging Shifts in Content Mediums
3 Key Concepts
The Fisherman Story
A parable about an American businessman advising a Mexican fisherman to work harder to build a large fishing empire, only to ultimately achieve the simple, relaxed life he already had. Gergely used this to question the pursuit of a startup for 10 years to eventually do what he was already doing (writing and sharing knowledge).
Comment is an Invitation for Refactoring
Gergely's philosophy that if a piece of code requires a comment to explain it, the code itself is likely unclear and should be refactored to be self-explanatory. This concept became a popular blog post that generated significant discussion on Hacker News.
Controllable vs. Uncontrollable Goals
A framework for setting objectives where controllable goals are actions one can directly influence (e.g., 'I want to write once a month'), while uncontrollable goals depend on external factors (e.g., 'I want to be promoted' or 'I want 20,000 subscribers'). Focusing on controllable goals is more effective for personal growth and motivation.
7 Questions Answered
For Gergely, his newsletter earnings now exceed his best year at Uber, which was around $320,000-$330,000 in total compensation in Europe, with the added benefit of uncapped growth potential as long as the newsletter grows.
His decision was driven by a promise to himself to take a risk after four years at Uber, combined with the stress of COVID-19 layoffs and the realization that he desired more control and responsibility than his middle management role offered.
Gergely typically publishes two posts per week: an in-depth, timeless article on Tuesdays and a more timely 'scoop' on Thursdays, sometimes with additional bonus posts.
Gergely uses a custom script to block distracting websites, sets a 20-minute timer for focused work to overcome inertia, and relies on self-imposed weekly publication deadlines to create necessary pressure.
Key downsides include loneliness due to lack of team interaction, a constant feeling of guilt about not working enough, unexpected stress from external validation (subscriber numbers), and difficulty taking meaningful time off due to continuous production demands.
His initial success was built on six years of consistent blogging on 'The Pragmatic Engineer,' which cultivated a loyal readership and established his authority, leading to rapid sign-ups when he launched the paid newsletter.
Aspiring creators should build significant depth and expertise in their chosen field, consistently share their knowledge in various formats, set controllable goals for their output, and be open to experimenting and adapting their approach.
17 Actionable Insights
1. Create Self-Imposed Deadlines
For entrepreneurs or creators, establish regular, public deadlines (e.g., weekly posts) to create external accountability and overcome the challenge of unstructured time, ensuring consistent output and productivity.
2. Force Focused Work Sessions
To combat distractions and get into a flow state, use tools like website blockers (e.g., host file scripts or browser extensions) and set short timers (e.g., 20 minutes) for uninterrupted, dedicated work.
3. Build Depth & Credibility
Become an expert in your chosen field by gaining real experience and working in environments doing interesting, cutting-edge things, which provides a strong foundation for sharing valuable insights and building an audience.
4. Consistently Share Knowledge
Regularly publish content (e.g., blog posts, newsletter articles, videos) over an extended period, even if initially for yourself, as this practice improves your craft and can eventually attract a dedicated audience.
5. Double Down on Audience ‘Pulls’
Pay attention to what content or topics generate significant interest and engagement from your audience, then invest more time and effort into those areas as they indicate strong demand and potential opportunities.
6. Set Controllable Goals
When pursuing new ventures, focus on setting goals that are within your direct control (e.g., ‘write once a month’) rather than external outcomes (e.g., ‘achieve X subscribers’), to maintain motivation and avoid frustration.
7. Clear Calendar for Focus
Intentionally minimize meetings and commitments to create large blocks of uninterrupted focus time, which is crucial for deep work and creative output in a creator role.
8. Evaluate True Motivations
Before making significant career shifts (e.g., leaving a stable job for a startup or creator path), deeply reflect on your core motivations (e.g., desire for small team work, long-term impact) to ensure alignment with your chosen path.
9. Take Calculated Risks
If you have sufficient savings, consider taking a professional risk on a non-traditional path, allowing yourself a period of time (e.g., six months) to explore and build a new venture without immediate financial pressure.
10. Start Side Projects
Engage in side projects to develop entrepreneurial skills, experiment with new ideas, and explore potential opportunities without the immediate pressure or expectations of your main job.
11. Recognize Creator Life Downsides
Be aware that a full-time creator life can be lonely and surprisingly stressful due to constant performance pressure and lack of traditional corporate structure; proactively seek community or shared workspaces.
12. View Creator Work as Business
Adopt a business mindset for your creator endeavors to help detach from personal stress, make sustainable decisions, and plan for long-term viability rather than solely focusing on the ‘creator economy’ aspect.
13. Experiment with Productivity
Continuously try different productivity methods and tools (e.g., Pomodoro, specific apps) and be prepared to adapt or rotate them, as your brain may get used to certain approaches over time.
14. Consider Content Medium
Strategically choose your content medium (e.g., written blog/newsletter vs. video/podcast) based on current market trends and audience preferences; for example, fewer people are writing in-depth blogs, which could be an advantage.
15. Enjoy the Process
Find genuine enjoyment in the core activities of your creator work (e.g., writing, researching, teaching) as this intrinsic motivation makes consistency easier and more sustainable long-term.
16. Proactively Plan Time Off
Consciously plan for and take meaningful time off to prevent burnout, even if it requires working ahead on content or adjusting expectations around continuous output.
17. Don’t Fear Pivoting
Be open to trying new things and pivoting your approach or venture if initial efforts don’t gain traction or if new, more promising opportunities emerge.
5 Key Quotes
I just honestly making tons of money doing a job that I loved. And this was at Uber or as a software engineer. And I'm now doing something I love. And in some strange way, I guess it even pays better.
Gergely Orosz
So I told myself like, look, four years later, Uber exists and I make a bunch of money. I owe it to myself to take a risk because then I'll have like, you know, four years of savings in my bank.
Gergely Orosz
If you want to write a book, the easiest way is go to a publisher and sign a contract, not because of the money and software engineering, you're not going to get much to live like $5,000 or something like that. That's what I was offered initially, but it's the pressure.
Gergely Orosz
One of the biggest, best things about doing what we do when you're in charge of your time is you can double down on polls.
Gergely Orosz
I always thought it's kind of ironic, but the more I read it, the more I thought he actually means something with it. And when I started this blog, the pragmatic engineer, I said, I'm kind of tired of my old blog being all over the place and there's no focus and no one really cares about it. I'm going to do what Jeff said. I'm going to publish, okay, it's not going to be twice a week, but I like for every two weeks, I'm going to publish an article and I'll do it for a year.
Gergely Orosz
1 Protocols
Jeff Atwood's 'How to be Famous on the Internet' Blogging Protocol
Jeff Atwood (recounted by Gergely Orosz)- Write a blog post.
- Do this three times a week.
- Do it for two years.