"Everyone should fail in a big way at least once before reaching forty"

The assertion champions failure as a teacher, not a verdict. A consequential stumble punctures the illusion of control, strips away perfectionism, and forces a clear-eyed inventory of strengths, blind spots, and values. When a plan collapses publicly, losing a job, shutting down a venture, missing a life-defining goal, the experience reframes identity: you are not your outcomes, and that separation breeds courage.

Before forty matters less as a rule than as a window. Early and mid-career setbacks arrive when reputations are still malleable, responsibilities may be fewer, and there is time to rebuild skills, networks, and confidence. Scar tissue formed then becomes strategic wisdom later: better risk assessment, sharper focus on essentials, and a deeper tolerance for uncertainty. Ambition becomes calibrated, still audacious, but grounded.

There is also moral texture. The usefulness of failure depends on how it is met: with accountability rather than excuse-making, with repair where harm was caused, and with disciplined reflection. Romanticizing collapse is empty; context and privilege shape how survivable a setback is. Safety nets, community, and prudent buffers matter. The invitation is not to court recklessness, but to choose endeavors whose upside justifies the stretch and whose downside you can ethically own.

Practically, that means taking bets that expose you to real feedback, not just safe iterations. Build a habit of postmortems. Separate self-worth from performance. Maintain reserves, financial, relational, emotional, so you can learn rather than merely endure. Seek mentors who can translate chaos into lessons. When you lead, use your scars to create cultures where experiments are expected and blame is rare.

The paradox is that a large failure, metabolized well, becomes a foundation stone. It cultivates humility without shrinking ambition, empathy without dulling edge. The fear of falling loosens its grip, and the horizon widens. The aim is to live boldly enough to risk meaningful mistakes, then mine them for insight, so the decades ahead are steered by hard-won clarity rather than fragile pride.