If You Knew You Were Going to Fail

We’ve all heard the question: If you knew you couldn’t fail, what would you do? It’s a classic coaching prompt, and for good reason. It nudges us to recognize where fear might be holding us back and invites us to dream big. But recently, I came across a twist on this question.

Seth Godin asks: If you knew you were sure to fail, then what would you do? If we failed, would it be worth the journey?

Think about that for a moment. What’s so compelling about this version is that it shifts the focus from the outcome to the process. This shift can be liberating, as it allows us to focus on the intrinsic value of what we’re doing, rather than external validation. It’s not about imagining guaranteed success; it’s about finding value in the experience, no matter where you end up.

If you knew your business idea wouldn’t take off, would you still pursue it because you’re passionate about what you’re building and who you’re becoming in the process? If you knew you wouldn’t win the race, would you still train because you love the way running makes you feel? If the relationship won’t last forever, is the connection worth it anyway?

These questions help us cut through external markers of success and focus on what truly lights us up. For example, pursuing a creative project or building something meaningful can be worthwhile even without traditional recognition. What endeavors would still feel meaningful—even if they weren’t successful by society’s typical measures?

For me, this perspective is a reminder that not everything needs to be measured by its result.

Sometimes, the journey, the change, the experience, and the growth are themselves the point.

So, I’ll leave you with this: If you knew you were sure to fail, what would you choose to do? And what does that say about what matters most to you?

With warmth,

Amy