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The Pragmatic Engineer: Deepdives

Long-form educational articles every Tuesday. These articles typically go deep into a topic relevant for software engineers or engineering managers, and tend to offer actionable advice.

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Headed for the Exit: the Great Engineering Leader Career Break

Trend: more CTOs, VPEs, and Heads of Engineering are walking away from their high-status, in-demand positions. There are many reasons, mostly related to AI, and to "founder mode"

Software engineering at a proprietary trading company: Optiver

A shift from a focus on latency to building better AI models, owning the full stack from applications to building custom hardware, very different incentives to most tech companies in play, and more

How building software is changing at Anthropic

A deepdive on what’s changed in how the leading AI lab makes software. Ever more code review and testing is done by AI, two-pizza teams very much alive, and more. Details from inside of Anthropic

Pushing software engineering limits with “napkin math”

Turbopuffer cofounder Simon Eskildsen on the benefits of longer tenure, using first principles to build durable software – and why founders should be cautious when raising VC money

What is “loop engineering?”

There’s talk about loop engineering, but what is it exactly? I looked into it, and found triggers, cron jobs, AI slop & more. Is it a “here today, gone tomorrow” trend?

Tech jobs market in 2026, part 3: hiring managers & job seekers

The market where nobody finds each other, the hottest market for AI-related positions, tough for engineering leaders, and more. Based on details from 50+ hiring managers & job seekers

Slow down to speed up: so much has changed in 6 months’ time

An overview of what’s changed in engineering during the last six months, how various tech companies are changing how they work, and why slowing down could be a sensible strategy

Why is Meta destroying its engineering organization?

Leadership at the social media giant has been on an AI-fueled rampage through its engineering org. We report what’s happened

State of the software engineering job market in 2026, part 2

Deepdive into the tech jobs market with exclusive data revealing AI labs are more attractive than Big Tech, native mobile & frontend roles are declining, management’s “great flattening”, and more

Ideas: slow down to speed up when working with AI agents

Devs are generating twice as much code (or more) than just 6 months ago, which is a problem for quality, reliability, and tech debt. A rational fix is available for these, but who’s acting rationally?