The Pragmatic Engineer

Gergé Oros had it all: a senior engineering role at Uber in Amsterdam with total compensation around $320-330k annually, stock options from Uber's IPO, and a clear path to senior management. But in April 2020, COVID hit and Uber laid off 20% of its workforce. As a manager overseeing 30 people, Gergé had to let half his team go. The experience shattered his belief in corporate loyalty. "I just didn't feel like good about it," he recalls. "It's just a corporate and I'm just a number." Two months later, during a holiday in July, he made a decision: he needed to leave.

He had made himself a promise years earlier—if Uber went public and he built up savings, he'd take a risk. That moment had arrived. His original plan was to leave, write a book called "The Software Engineer Guidebook," then raise venture capital for a startup. But life had other plans.

Before launching the newsletter, Gergé spent about 10 months exploring different ideas. While writing his book, he published two others—"Building Mobile Apps at Scale" and a guide on tech resumes—which surprisingly made about $100,000 in his first year through self-publishing. This unexpected income forced him to reconsider his path. He realized that while books were lucrative, they were unpredictable: "I didn't like it. I didn't know if today I'm going to be making like 50 bucks or 10 bucks or 300 bucks."

Then he discovered paid newsletters. Reflecting on his own decision-making, Gergé realized he had a deep well of ideas and the discipline to write. "I collected ideas of what I would write about. And I had this super long list." He announced The Pragmatic Engineer in late 2021, committing to write one deep-dive article per week about software engineering. He told his wife he'd give it six months and either refund annual subscribers if it failed or stick with it if it showed traction.

His production process was intensive: researching for a day or two, drafting, getting feedback from trusted sources, and working with a professional editor (a former journalist). Most pieces ran 5,000-6,000 words. To stay productive, he blocked distracting websites and created external deadlines—eventually expanding to two posts per week (one in-depth Tuesday piece and a timely "scoop" on Thursday).

The first subscribers came primarily through word-of-mouth and direct outreach from readers familiar with Gergé's previous writing and Twitter presence. However, the real inflection point came when Substack introduced its recommendations feature. "This one was one Substack introduced recommendations, which has been a massive growth engine," Gergé explains. Being one of Substack's top technology newsletters, he benefited significantly from algorithmic recommendation placement.

Growth accelerated dramatically: the newsletter hit 50,000 subscribers in its first nine months, then added another 100,000+ subscribers over the next five to seven months. By the time of this podcast, The Pragmatic Engineer had 189,000 subscribers, growing at nearly 1,000 new subscribers per day (80,000 in the previous 90 days).

What worked was the positioning. Gergé identified a gap in the market: software engineers wanted practical, in-depth career advice, not generic business content. His credibility from Uber, Skyscanner, and other top tech companies gave him authority. The subscription model—free tier with limited access, paid tier for deeper content—proved resilient. "There's thousands of people paying for the newsletter. It's a single digit percentage, but it's a very, very healthy one."

The biggest surprise was the financial upside. "Now I am making more in compensation that I made at Uber," he says. Crucially, unlike his old job, there's no artificial cap: "my burnings are keep going up as long as the news that it was growing. So there's no theoretical cap on this."

What proved harder: the isolation. After years of team collaboration at major tech companies, going solo was a shock. "One is obviously it's lonely. So I do miss, I had a really good team at Uber." He compensated by joining shared workspaces. Also challenging: the pressure. "It is surprisingly stressful," he admits, noting the competitive nature of the newsletter economy and the weight of thousands of paying customers' expectations.

Gergé is now a full-time writer generating more revenue than his six-figure Uber salary. He maintains a disciplined schedule with two posts per week, uses focus techniques (blocking websites, 20-minute timer sessions, apps like Centered), and carefully guards his time. He discovered that constraints and external deadlines—ironically, the things he disliked about corporate life—are crucial for his output. He even secretly used newsletter content as chapters for his software engineering book, echoing Alexander Dumas's strategy of writing serialized fiction for magazines.

His advice to others considering this path: create artificial deadlines and constraints, as external accountability drives output. Tell people you'll deliver something weekly, and you'll deliver. Build a business model with recurring revenue (subscriptions beat one-time sales). And understand that the downsides—loneliness, self-doubt about productivity, stress—are real, but the upside of autonomy, creative control, and unlimited earning potential can outweigh them.