The Drawer Where I Keep My Doubts

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“After a lifetime of answers, I find myself returning to my doubts—about the world, about meaning, about myself,” writes the professor, author and essayist Jeff DeGraff, aka The Dean of Innovation. The Drawer Where I Keep My Doubts, is a beautiful meditation on the power of questions and having the courage to keep them close to our hearts, in order that we might try, in Jeff’s words, “to attempt to make peace between who we are and who we become.” After all, some things aren’t meant to be resolved on schedule. Doubt, hesitation, unfinished questions, ‘small hauntings’—these aren’t failures of willpower, but the raw material of growth.

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THERE’S A DRAWER IN MY STUDY that doesn’t close all the way—jammed, as if by conscience—with old notebooks, foreign coins, expired IDs, and one letter I never sent. I keep meaning to clean it out, but I don’t. Not because it’s precious, but because it’s honest. It’s where I keep things I don’t yet know what to do with. Which is to say: it’s where I keep my doubts.

Some people organize their lives by goals. Others, by memories. I seem to organize mine by unfinished questions—most of them too small for theology and too big for to-do lists. Questions like: Why do I remember certain faces from elementary school more vividly than colleagues I worked with for years? Why do I feel a pang of guilt when I throw away a birthday card, even if I barely knew the sender? Why did I save that letter I never mailed—whose silence did I preserve by not sending it?

The drawer is full of these small hauntings.

There’s a matchbook from a bar in Berlin where I had a long, circular conversation with a physicist about whether time is real. Neither of us reached a conclusion, but the moment felt important—like the universe paused and listened in. There’s also a cracked plastic wristband from a hospital visit that ended in recovery, not tragedy. But even survival feels complicated when you’ve prayed for someone else who didn’t make it.

I sometimes think of this drawer as a sort of reliquary—not of faith, but of suspended belief. It holds the relics of times when the world didn’t quite make sense, and I didn’t quite insist that it should. Times when I let the mystery remain mysterious.

We aren’t very good at that anymore, culturally speaking. Doubt, like clutter, is something we’re taught to “declutter.” We’re coached to be decisive, certain, manifesting, optimizing. There are entire self-help empires based on the premise that if you don’t know what you want, you’re already behind. But what if the pause before clarity is sacred? What if indecision is not a flaw, but a form of listening?

I once asked a rabbi friend how he dealt with the contradictions in Scripture. He shrugged and said, “We argue with God all the time. That’s how we know He’s still talking.” That stuck with me. Maybe doubt is the other side of dialogue. Not the absence of faith, but its friction.

The drawer reminds me of that. Its contents are oddly devotional. A subway token from New York—the kind they haven’t used in decades. A boarding pass to a city I don’t remember visiting. A photograph of a place that might be Italy or might be a dream. Each one insists on meaning, but doesn’t tell me what that meaning is.

I suppose what I’m trying to say is this: some truths don’t arrive fully formed. They arrive like seeds—tiny, closed, waiting. And sometimes it takes years to figure out what they’re meant to grow into. If we rush too fast toward certainty, we bury them. But if we keep them close—mismatched, unresolved, a little bit dusty—they eventually bloom in their own time.

The drawer is also where I keep little notes I’ve written to myself. Not the “buy milk” kind, but the “don’t forget you believed this once” kind. I have one that says, “Wonder before wisdom.” Another that reads, “Don’t make the answer too small.” I don’t remember writing them, which somehow makes them truer. Like they were dictated by a part of me I can only access when I’m not trying to be profound.

Sometimes when students or clients ask me how I became “successful,” I want to point to that drawer. Not the bookshelves or diplomas. The drawer. Because in that mess is the part of me that didn’t try to control the outcome. That didn’t hide the half-finished thought or the shaky intuition. That didn’t pretend to be certain when I wasn’t.

Innovation, after all, doesn’t come from what we know. It comes from what we’re willing to not know—what we’re willing to explore, to question, to challenge. And that takes doubt. Creative, constructive, illuminating doubt. The kind that makes you pause at a fork in the road and say, “I wonder what would happen if…”

There’s a note in the drawer, too, scribbled on a napkin, that says just that: “I wonder what would happen if…” It doesn’t say what the “if” was. But it must’ve mattered enough to write down.

Of course, not all doubts are beautiful. Some are bitter. Some keep you awake at night, revisiting conversations you can’t redo or decisions you wish you could unmake. The drawer has those, too. The unsent letter? It was an apology. One that never found the courage or the moment. I don’t know if I was right to hold it back. But there it is, folded inside its unsealed envelope, waiting in silence.

Maybe that’s what the drawer is for. Not to sort or resolve, but to hold. Like a sanctuary for the unfiled parts of ourselves. A place that says, “You don’t have to figure it out yet. Just stay close. Just keep wondering.”

Every once in a while, I open it—not to clean it out, but to be reminded. That not everything that matters has a label. That we are made, in part, by what we carry but do not display. That there is grace in the unspoken, the unfinished, the unresolved.

And on rare occasions, I take something out.

Not to throw it away. But to put it on my desk. To let it sit beside the urgent paperwork and the curated bookshelf. To let it whisper its question again. Maybe this time, I’ll hear the answer. Or maybe I’ll just appreciate the question more.

We live in a world that rewards clarity, but it’s often doubt that enlarges us. That cracks us open. That lets light through the places we thought were already settled.

So if you have a drawer like mine—a place where memory and mystery mingle—don’t rush to tidy it. Let it be sacred. Let it be messy. Let it be yours.

And if you don’t have one, maybe it’s time to start one.

Begin with a question you’re not ready to answer.

Fold it carefully.

Place it inside.

Close the drawer—just enough to let it breathe.