Colby Bessera - Learning to Be Unabashedly Yourself
Unabashedly Yourself: A Conversation With Young Writer Colby
Some conversations are extra special. This one was with my great-nephew Colby: writer, storyteller, maker of terrible jokes, and now a freshman at Oberlin College. Colby is my sister Fanny’s grandson. She’s number three of us eleven, and he’s the eldest of her daughter Annie’s two kids, which makes him number three’s number one’s number one!
We talked about creativity, courage, leaving home, and why human stories matter so much right now.
A Lifelong Love of Stories
Colby has loved reading since he was two or three years old. There are photos of him as a toddler, hunched over library books, determined to figure them out. At family dinners and gatherings, he’d be reading, reading, reading. How often do you hear an adult tell a child tostopreading? His second-grade teacher even sent a note home about it.
Today Colby writes poems, short fiction and the occasional delightfully confusing play. He loves novels, video games, indie music, and binge-watching TV with his family. His favorite kind of storytelling is interactive, like Dungeons & Dragons and story-driven video games. Watching other people shine inside a world he’s created, he says, is one of his greatest joys.
Growing Up Among Young Artists
Colby graduated from Houston’s High School for the Performing and Visual Arts, where his younger sister, Frances, studies now. Every student there is pursuing an art form: theater, writing, dance, music, even mariachi. Colby calls being surrounded by that much talent and drive for four years an absolute joy. He wouldn’t be who he is without his classmates.
Many of them, he says, know what theycando and love art deeply. Figuring out how to use it in their lives is the harder part.
Eulogy for a Coachman
For his senior showcase, Colby wrote and staged a short play calledEulogy for a Coachman. I was lucky enough to be in the audience. He cast his sister, Frances, as the Fairy Godmother and his classmate Paloma as the Coachman.
The play imagines one of Cinderella’s mice, transformed into a coachman for the night, who doesn’t want to change back. The Fairy Godmother offers him a choice: he can stay human, but only if he forgets everything about his past.
Where the story came from
Colby told me the play grew out of his own senior year. He was preparing to leave Houston, where his whole family lives, for a new state and a new life. He admits he spent much of the year scared out of his mind. The Coachman became a way of arguing with himself: What do I take with me? What do I leave behind?
His conclusion: stepping into a new life often means leaving things behind, even things you love. For the Coachman, that meant letting go of the innocence of being a mouse.
A happy accident
The play almost didn’t happen. Colby first started writing a piece about where writers fit in a world shaped by AI, then realized halfway through that it was far too long. Around the same time, his school stagedCinderella, and students got to watch a preview. Seeing the mice transform into the coachman stuck with him. A few days later, he was writingEulogy for a Coachman.
Art Is Meant to Connect Us
Colby has strong feelings about treating art as a competition. Ranking something so personal and subjective, he says, isolates artists. When people compete, they hide their work. When they collaborate, they share it, and the whole point of art is connecting with other people.
I couldn’t agree more. A curious, collaborative spirit breeds abundance thinking, and that matters everywhere in life, especially in a season when so many people feel isolated.
Choosing Oberlin
Colby had several college options and waited until after his acceptances to visit. Oberlin won him over because it felt warm, exciting, and, in his words, “weird enough” in the best way. Everyone seemed to have unique ideas and to respect one another’s differences.
Students start undeclared, which Colby appreciates. One of his first seminars? Video Games and Politics. Weird enough, indeed.
Advice for Parents of Young Artists
When a child loves the arts, parents naturally worry: how will they pay the bills? Colby says those worries are valid. Even so, he believes a person’s happiness and fulfillment matter most.
His advice comes down to two words: support and transparency.
Both of his parents are artists. His father is a musician and his mother is a dancer. They told him honestly that you can do what you love for a living, and that it takes sacrifice, hard work and sleepless nights. They also promised to be there for him no matter what. Colby calls that honesty and support the greatest gift they’ve given him.
Advice for Young Creatives
To young people trying to figure out how to use their gifts, Colby says: if you’re passionate about something, pursue it. He also gently pushes back on the pressure to monetize every talent.
Making a living from your art is valuable. So is keeping art in your life for yourself. Colby hopes to become a writer, and even if another profession captures his heart, he’ll always write. Creating for your own joy has real value too.
That reminded me of a truth I come back to often: caring for yourself is a gift to others, and caring for others is a gift to yourself. Keep creating, whether or not you ever share it.
Creating Something New
Colby believes the ability to make something that never existed before is miraculous, a true God-given gift. It’s why every person, at some point, loves some form of art. Stories connect us because they carry other people’s voices and emotions, and we see ourselves in them.
That’s exactly why we do this podcast and so much of what we do at One of Eleven Productions: to connect people through story.
Colby also pointed out that whatever humans make, from laws to art to ideas, will never be perfect, and that’s okay. We can keep making things new. The danger comes when we stop creating.
Perfect Writing Misses the Point
So many people tell me, “I’m not a writer.” Colby’s answer: if your writing feels perfect, you’ve missed the point. There’s a big difference between being proud of something you made and believing it’s flawless.
Everyone hears a critical inner voice, Colby included, every time he writes. Sometimes you have to quiet it. Sometimes it helps you improve. And you never have to show your writing to anyone if you don’t want to. The sweet spot is feeling proud that you created something, flaws and all.
On AI and Human Writers
When my team asked Colby about a challenge he’d overcome, he named the false idea that human writers will become irrelevant because of AI.
He has mixed feelings about AI. He sees potential in it as a research tool or helper for things you already know how to do. Trouble starts when it replaces the creative act itself. AI recombines existing work, he says, like a mythical creature stitched together from many parts. And even if its style became flawless, there would be no lived experience or emotion behind it.
Colby’s Word for the Year: Unabashedly
Colby chose a wonderful word for his year:unabashedly.He has wrestled with a bit of imposter syndrome, wondering whether he deserves his gifts and opportunities. This year, he’s learning to quiet that voice and be completely comfortable with how he talks, connects and loves the things he loves.
He admits he hasn’t mastered it, and he doesn’t think anyone ever fully does. We can still try to be unabashedly ourselves.
Find Small Joys
Colby’s parting thoughts: we live in uncertain times, and it’s easy to feel helpless. The greatest thing we can do is find small joys, in creating, in being with people, in a quiet moment with a good book. His best ideas come when he’s at peace on the couch, watching a show or simply thinking.
Even when the world feels chaotic, he trusts that he’ll carve out his place in it and persevere.
Key Takeaways
Support young artists with honesty and love.
Art connects us best when it’s shared and collaborative.
Growth sometimes means leaving cherished things behind.
Create for yourself, whether or not you ever share it.
Pride in your work matters more than perfection.
Small joys spark big ideas.
Be unabashedly yourself.
Listen to the Full Conversation
Hear my whole conversation with Colby onConversations with Carroll, on Spotify, Apple and YouTube. If you know a young creative or a parent of one, please share it with them.
Colby, I’m so proud of you, and I love you so much. Thank you for this gift of a conversation.
Thank You, Father.
