Even If It Fails: A Philosophy of Meaningful Work

June 20, 2025

Contemplation

There’s a quiet tragedy in realizing you gave years of your life to something that didn’t matter—not because it failed, but because you weren’t changed by it. That, to me, is the real nightmare. Not the failure. Not the silence at the end of effort. But the hollowness. The sense that your time—your life—has slipped through your fingers like sand, leaving nothing behind but dust and regret.


The only antidote I know is this:
Choose work that would’ve been worth it even if it doesn’t work.


Pursue what stretches your soul, sharpens your mind, and ignites your curiosity. Build things that leave you wiser, kinder, and more human—regardless of whether they gain traction or applause. That’s not just career advice. That’s a way of being.


These are the kinds of projects that speak to something deeper than ambition. They reach into vocation. They whisper, “This is worth your time simply because of what it asks of you.” When you find that kind of work, you stop calculating return-on-investment in numbers, and start measuring in character, in craft, in joy.


And that’s where regret loses its grip. Because you’re not chasing a payoff, you're walking a path. You're living into a story that’s meaningful, not just profitable. These projects won't always win—but they'll always leave you transformed.


Flow becomes familiar. Curiosity becomes compass. Evenings arrive not with the anxiety of "What was it all for?" but the quiet gladness of a day spent in alignment with what matters.


That’s the only kind of success that never fades. The kind that stays with you even when no one else is watching.


That’s a work of meaning.


And for that final insight, credit where it’s due: the seed of this reflection was planted by DHH,