Failing Well: A Practical Guide to Growth for Technical Writers
summary
Argues failure is systemic not personal and names three practical failure modes: a gap between what docs need and what organizations allow, failed initiatives that reveal information culture, and being trapped without power. Gives concrete examples—maintaining 17 versions of installation guides, engineers repeatedly asking questions already in docs—and recommends measurable moves: collect metrics, run experiments (hackathons, LLM/AI trials), publish findings (internal email → blog), and grow through restlessness courage generosity. Evidence of partial wins is candid and tactical.
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chapters (20)
- 0:00Introduction
- 1:05Failing well oxymoron
- 2:31Failure in tech writing
- 3:16Repeated failure scenarios
- 8:38Failure as systemic issue
- 11:23Embrace failure mindset
- 12:48Why growth matters more than just doing the job
- 14:15When growth isn’t possible
- 16:01Qualitative growth needed
- 17:47Stagnant vs dynamic seniority
- 19:12Principles for growth
- 20:37Advocate for tech comm
- 22:22Critical reflection shift
- 23:26Courage to act
- 24:32Generosity in community
- 25:37Perpetual learning
- 26:40Speak up courage
- 28:24Future of documentation
- 30:56You have agency
- 32:03Q&A








