Close your eyes to the present and scout the whole future terrain

When a national nonprofit asked me to help them budget around grant applications, their initial list read like a shopping catalog: ‘Here’s a $100k ask, here’s $200k, here’s $50k.’ They prioritized only by size—and often burned time chasing big grants that had little chance of coming through. I suggested something radical: let’s scout the future. Could they win each grant? At what odds? Some $50k requests were virtually locked down; others weren’t. Rewriting those applications almost overnight, the team shifted energy to mid-sized grants where they had a 70% shot and gained $35k on paper, instead of a 10% chance at $200k. The result? The actual awards smashed projections by 20%.

That’s scenario planning in action: imagining each path forward, from best to worst, then ranking by both likelihood and impact. All those possible futures turn a messy field of guesses into a navigator’s map.

It wasn’t magic—just a simple exercise of listing “what if” scenarios, assigning them odds, and weighing their stakes. As they rolled this out across other departments, everyone from the CEO to the program managers learned to think like a scout: foreseeing pitfalls and spotting the hidden high-probability wins that get lost in an unexamined to-do list.

Take your next major decision—big purchase or career choice—and treat it like a pitch book. List every ‘what could happen,’ give each outcome a rough probability and impact score, and see which forks in the road deserve the most focus. You’ll spot pitfalls months in advance and turn fuzzy hopes into clear targets. Start this afternoon; bring your map to tomorrow’s meeting.