Ep 32 – From Idea Overload to Execution – A Strategist’s Guide to Prioritization

This is a free preview of a paid episode. To hear more, visit longtermstrategy.substack.com Your organization has 37 brilliant projects. You have bandwidth for maybe 5. Now what? This is the reality facing leaders everywhere: expensive master plans that deliver impressive lists of initiatives but zero guidance on which ones to actually pursue. Meanwhile, your …

Stop Calling It Recovery: Why Your Business Needs a Different Target

When disaster strikes, the language leaders choose reveals everything about their future. In late October 2024, Hurricane Melissa tore through Jamaica as a Category 4 storm, causing widespread devastation. Within days, business leaders across the island were using the same word: “recovery.” Getting back to where they were before the hurricane hit. But here’s the …

Chronicles from a Caribbean Cubicle 2025-11-09 14:19:17

Why Playing It Safe Will Erase Your Leadership Legacy The conventional wisdom says: stay focused, deliver on your core responsibilities, don’t overstep. But the leaders who’ll be celebrated a generation from now are ignoring that advice entirely. Picture this: You’re running a major public sector organization. Every performance indicator is green. Your board loves your …

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