The archive
Issue #006
Project Management Horror 8 min read· 5 Jul 2026

The Outsourcing Nightmare

A partnership with a tech team in Asia. A project that should've taken 3 months. And a revolving door of project managers that turned it into a 2-year nightmare. The story of how the Accidental CTO was born before the title existed.

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CTO takeaway

The lesson, minus the scar tissue.

  • Never outsource a project you don't understand yourself. You can't manage what you don't know.
  • Track deliverables, not timelines. If they can't show you working code, they're not 'working on it.'
  • Escalate early. The first time a PM changes, ask why. The second time, raise it with their leadership. The third time, walk away.
  • The best leaders aren't the ones who avoid disasters. They're the ones who take ownership when disasters happen.
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