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Hopeful Thinking: ‘I didn’t know I couldn’t’

Дата публикации: 01-08-2026 09:45:04

Thoughts on the art of figure-it-out ability

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Editor’s note: Wil Darcangelo, the author of the “Hopeful Thinking” column, and pastor at the Unitarian Universalist minister of the First Church of Lancaster, is changing the title of the column to “Our Common Dharma,” which he says “more accurately represents the synthesis of world traditions and spirituality that I undertake in my writing.”

I find the most capable people aren’t the ones who already have every answer. They’re the ones who trust themselves to learn the next one.

There was a scene in the 1968 Barbra Streisand film “Funny Girl” that taught me one of the most valuable lessons of my life.

The character Fanny Brice is desperate for a chance to perform when the producer’s assistant Eddie Ryan asks her a simple question: “Can you roller-skate?”

Without missing a beat she answers, “Can I roller-skate!”

If you’ve ever spent time around New Yorkers of a certain generation, you recognize the way she makes that turn of phrase immediately. Grammatically it sounds like a question, but everyone knows it’s a declaration. It means, “Of course I can!”

There was only one problem. She couldn’t.

What follows is one of the funniest scenes in the film. Fanny finds herself trying to learn to roller-skate in front of a live audience. She stumbles. She flails. She barely survives the routine. The theater manager is horrified.

The audience, however, can’t stop laughing.

Afterward, one of the other skaters in the bit she just nearly ruined, reminds her, “You said you could skate!”

Fanny shrugs and replies: “I didn’t know I couldn’t!”

I’ve loved that line ever since I first heard it. Not because it encourages pretending to know things you don’t. But because it reminds me that there is an enormous difference between not knowing how to do something and believing you could never learn it.

Long before I entered the ministry, I made some of my living as a jazz singer. I loved performing, but I also loved using music as a way to raise money for local nonprofits. I produced a Sunday jazz brunch series and also for several years produced a performing arts series at Rollstone Church where I grew up. Life was full of music.

Then came the Great Recession in late 2007. Almost overnight, my jazz gigs dried up. The performances stopped.

Fortunately, I’d developed some wonderful friends in a few of the marketing departments who had sponsored my events over the years. Instead of simply saying they were sorry, several of them found another way to help me through those years. They started hiring me to do light renovation work in their homes.

They’d say to me, “Do you know how to hang sheetrock?” or “Do you know how to lay tile?”

I’d immediately think to myself, ‘Can I roller-skate!’

The truthful answer was almost always no. I did not know how to do sheet rock or tile, yet. But somewhere in the back of my mind, I’d be thinking about that scene in the film. And how the character’s fearlessness ultimately led to her success.

So I’d go home, learn everything I could, study the instructions, watch videos, ask questions and show up ready to work. When in doubt, I’d just follow the directions on the package of the materials I was about to work with. Which is good advice. Read the directions.

One project led to another. Drywall and tile became finish carpentry which became flooring which became framing, and on it went. Before long I was doing work I never imagined I would know how to do.

Today, much of my home I renovated myself. My husband and I spend time at a cabin in Vermont that I built with my own two hands. The theatre skills I learned years ago — building sets, making props, solving creative problems — expanded into all forms of making and creating, which eventually found their way into my ministry through stained glass, woodworking, restoration projects and all sorts of creative things I could never have imagined when I was singing jazz. (Which, by the way, was also a thing I started doing because I didn’t know I couldn’t.)

Looking back, it kind of amazes me how many chapters of my life grew out of simply believing in my ability to just figure it out.

There are two very different kinds of confidence. One says, “I already know how.” The other says, “I don’t know how … yet.”

The first is useful. The second changed my life.

We often imagine confidence as certainty. We think confident people possess all the necessary knowledge before they begin. But that’s almost never how life actually works.

Our most meaningful accomplishments begin with curiosity, resourcefulness and a willingness to be a beginner.

Most every expert we admire once stood exactly where I was back then — essentially unable and definitely inexperienced, but believing I’d figure it out.

Somewhere between childhood and adulthood, a lot of us adopt a dangerous assumption. We are trained to believe we should only attempt the things we already know how to do.

But real wisdom isn’t about becoming more cautious about what we’re willing to try. It’s becoming more confident in our ability to figure it out.

That doesn’t mean pretending to have expertise that we really don’t. Obviously, if someone asked me if I know how to perform brain surgery, my answer would not be, “Of course I know how to roller-skate.“

It means trusting that we human beings are remarkably capable of acquiring new skills when we approach them with confidence, persistence and curiosity.

Looking back, I realize those friends who hired me during the recession gave me much more than work. They gave me evidence that I could become someone I wasn’t yet.

Whenever someone asks whether I know how to do something I’ve never done before, I still hear Barbra Streisand’s voice saying: “Can I roller-skate!”

And then I remember the line that mattered even more: “I didn’t know I couldn’t.”

That’s one of the healthiest assumptions we can ever make. Not that we already know how. But that our future selves may know things our present selves just haven’t learned  … yet.

Wil Darcangelo, M.Div, is an ordained Unitarian Universalist minister of the First Church of Lancaster at the Bulfinch Meetinghouse in Massachusetts, progressive theologian and essayist on optimistic spirituality in the Information Age. Follow him on Substack, Facebook, Instagram, TicTok and YouTube.

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