When to Pivot: Decoding the Moment When a Big Change is Better Than Sticking to Plan

Early in PayPal’s story, Max Levchin and team realized their big bet—encryption software for handheld devices—was completely out of step with the market’s timeline. With technical brilliance but no customer demand, they kept hitting walls. Rather than stubbornly pushing forward, they inventoried what they’d built: advanced crypto libraries and server-side security know-how. They scanned for adjacent needs and noticed a rabid, unmet demand among eBay users for easy, online payments, even though this had little to do with handheld devices.

Making the leap, they pivoted away from their cherished initial vision, risking the confusion of critics and the disappointment of early supporters. Their crypto tech became the backbone for a new payment system, which almost overnight became a viral hit on the web, not on devices. Every big startup in the book went through some version of this: initial ideas that didn’t stick led to bold pivots, often built out of stuff nobody else wanted or noticed.

Strategic pivots aren’t guesses—they’re structured experiments. Behavioral strategy research shows that success in dynamic environments comes to those who recognize the point when sunk cost thinking (“we’ve already invested so much”) gives way to opportunity cost thinking (“what else could we do right now that might work better?”). The key is tracking evidence and being willing to use what you’ve got, not what you hoped to have.

When you sense an idea is losing steam, get honest about what’s working and what’s not—write down your wins and your setbacks without sugar-coating. Challenge yourself to see how your assets could solve an adjacent need or appeal to a different audience, making sure to leverage what your team does best. Try a bold, low-risk experiment—just one—and see what changes when you pivot. Success often waits for those willing to move on, as long as they learn from every version. Give this a try next time your plan meets serious resistance.