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Stuff I Learned at Carta

Career Advice in 2025

Rough notes on learning Wardley Mapping

Should we decompose our monolith?

Numbers Go Up

Your First 90 days as CTO or VP Engineering

No Wrong Doors

Notes on how to use LLMs in your product

Building personal and organizational prestige

Solving the Engineering Strategy crisis

Migrations: the sole scalable fix to tech debt.

Digg's v4 launch: an optimism born of necessity (2018)

A Forty-Year Career (2019)

LLMs are showing significant promise at mediocre solutions to very general problems

Writing an engineering strategy

Better to micromanage than be disengaged

A brief rant on converging compliance regimes

Measuring an engineering organization

Company, Team, Self

The Flying Wedge

Staff Engineer Archetypes

Reminiscing: The Retreat to Comforting Work

Downturn career decisions

One-on-ones with executives

How to Present to Executives

How to Estimate Disk Space

Work on what matters

Reading a Profit and Loss Statement

Founding Uber SRE

Platforms change but cool URIs don't

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