Lessons Learned

January 2026

• Jan 10, 2026TechnologyAvoiding Common Automation Mistakes and PitfallsThe failure patterns that matter, which are rarely technical. Automation amplifies whatever it runs, so a process that is slow because of unnecessary steps becomes a faster version of the same flawed design. The diagnostic question is what this process would look like if it were perfect, which often points to redesign rather than automation. Knight Capital's 2012 collapse combined untested code, no anomaly monitoring and no kill switch.22 MIN8.8k

December 2025

• Dec 29, 2025TechnologyRecognizing Common Security BreachesEquifax had the Apache Struts patch for CVE-2017-5638 available two months before its breach began, and the flaw sat unpatched for 143 days until discovery while attackers took data on 147 million Americans. The 2024 Verizon DBIR, built on over 30,000 incidents, keeps finding the same short list behind most breaches: credentials, unpatched vulnerabilities, misconfiguration, social engineering, insiders and compromised suppliers.24 MIN21.4k
• Dec 23, 2025TechnologyCommon Analytics Mistakes and Their ImplicationsHewlett-Packard found employees living far from headquarters quit more in their first year, strongly and significantly, and changed recruiting to favor nearby candidates. The confound was compensation: those campuses paid below local market, so staff both commuted from cheaper suburbs and left for better-paying competitors. Proximity had nothing to do with it. Correlation misleads through confounding, reverse causation, and spurious matches that are inevitable at scale.25 MIN44.4k

October 2025

• Oct 9, 2025Work SkillsCommon Reasons Projects Fail: Understanding PitfallsThe Sydney Opera House remains the archetype, approved in 1957 against a four-year timeline and an estimate near 3.5 million, then finished 14 years later at roughly 49 million because the sail roofs had not been engineered when the project was approved. Engineering proceeded alongside construction, forcing constant redesign. His fix is reference class forecasting, anchoring estimates to how comparable past projects actually turned out rather than to bottom-up optimism.19 MIN49.8k

July 2025

• Jul 17, 2025ExplainersCommunication Breakdowns: Real-World ExamplesThe pattern repeats across domains: the people who know are structurally unable to make the people who decide act on it. Mars Climate Orbiter failed not because one team used pound-force seconds and the other newton-seconds, but because nobody verified the assumption, and the spacecraft arrived at 57 kilometers altitude instead of the planned 226. James Reason found inadequate communication contributed to 73% of the 90 aviation accidents he analyzed.28 MIN65.0k
• Jul 16, 2025ExplainersDecision-Making Failures Explained Through Real CasesKodak built the first digital camera in 1975 and spent decades protecting film margins above 60 percent before its 2012 bankruptcy. Blockbuster's 9,000 stores and 65 million members could not be weighed against roughly 800 million dollars a year in late fees. Nokia's collapse from 40 percent market share traces to INSEAD research showing middle managers feared reporting how far Symbian had fallen behind.29 MIN18.9k
• Jul 15, 2025ExplainersProduct Decisions That BackfiredSnapchat shipped its 2018 redesign without extensive user testing and pushed through negative early feedback; a petition passed 1.2 million signatures and Snap reported its first daily-user decline, about 3 million, from 191M to 188M. Windows 8, Digg v4, Google+, the Fire Phone and Qwikster repeat four patterns: ignoring feedback, designing for hypothetical users, adding complexity rather than value, and changing too much at once.35 MIN55.0k