The Long and The Short Of It 416. FOYF
Sep 15, 2026
Jen’s vacation takes an unexpected dive while learning to hydrofoil, sparking a lively conversation about falling, persistence, and the courage to try again. They explore how encouragement makes failure feel safer, how to replace “can’t because” with “can if,” and why deliberately chasing more low-stakes face-plants can open the door to bigger possibilities.
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Jen Waldman Learned Hydrofoiling Through Repeated Falls
- Jen Waldman repeatedly fell, swallowed seawater, and struggled to stand while learning hydrofoiling.
- Her instructor normalized failure by warning that beginners might not stand during their first week.
Not Knowing The Conditions Helped Jen Persist
- Jen returned each day, eventually riding with the foil above water and copying an advanced rider’s posture.
- She later discovered that her first day’s conditions were unusually difficult, but not knowing helped her persist.
A Clear Reward Makes Failure Worth Repeating
- Jen’s decision to say yes to everything made persistence easier when someone else planned her vacation.
- Watching skilled foilers made the struggle worthwhile because she could see the reward waiting beyond beginner failures.
