We have to continually be jumping off cliffs and developing our wings on the way down.

The image of leaping from a cliff and growing wings mid-fall captures a philosophy of action under uncertainty: you commit first, then acquire the skills, confidence, or resources needed to survive. It frames creativity and personal change as inherently risky—there is no fully safe rehearsal for a new life, job, or artistic project. The metaphor also implies that growth is accelerated by necessity: once you’ve stepped into the void, adaptation becomes urgent and possible. Attributed to Vonnegut, it aligns with his recurring skepticism about tidy plans and his emphasis on improvisation in a chaotic world, though the sentiment is broader than any single Vonnegut theme.