From Banjo to Memoir: Finding Meaning in the Messy Middle of Life

I wasn’t quite sure what to expect going into this conversation with Matthew Check, but I knew it would be interesting.What I didn’t expect was just how layered it would be.Matthew is a musician-turned-author whose memoir, What Would Philip Roth Do?, weaves together love, identity, creativity, and a fair amount of humor. But what stayed with me after our conversation wasn’t just the story itself. It was the process behind it—the discipline, the vulnerability, and the willingness to tell the truth even when it would be easier not to.We talked about what it means to write honestly, how creativity actually works (hint: it’s not always inspiration), and why memoir is less about recording events and more about making sense of them.There’s also something deeper running through all of this. Matthew’s story—whether he’s talking about bluegrass music, relationships, or imagined conversations with Philip Roth—keeps circling back to identity. Who am I? How did I get here? And what do I do with that truth once I see it clearly?If you’ve ever wrestled with your own story, or wondered whether it’s worth telling, I think you’ll find something here.Resources Mentioned* Matthew Check’s website* What Would Philip Roth Do? * Matthew Check on Spotify and Apple Music (linked from his website)* Bright Eyes: Surviving Our Monsters and Learning to Live Without Them by Bridey Thelen Heidel (mentioned in conversation)* Philip Roth’s booksThe Big TakeawayTelling your story honestly is less about getting every detail right and more about having the courage to say, “This is how I see my life,” and standing behind it.Bulleted Summary* Memoir is crafted, not just remembered. It requires shaping events into meaning* Creativity isn’t only inspiration; it’s also discipline, repetition, and showing up* Humor can open the door to truth, especially in painful or vulnerable moments* A good editor goes beyond fixing your writing to helping you discover what you’re really saying* Identity often reveals itself through unexpected connections (like bluegrass and Jewish heritage)* Writing a memoir forces a deeper question: “Am I willing to be this honest in public?”Practical Tips* Don’t wait for inspiration. Build a habit of showing up consistently* Find an editor or collaborator who understands your voice, not just your grammar* Write freely first; decide later what stays and what goes* Use humor where it naturally arises. It can make difficult truths more accessible* Engage with other writers or creators. You’re more likely to find the right collaborators that way* If you’re telling your own story, focus on meaning, not just chronologyQuote to Ponder“I really do want to make a statement about how I see my life and what happened.”When Your Life Becomes the MaterialIn this episode of The Alignment Show, I sat down with Matthew Check to talk about his memoir, What Would Philip Roth Do? But the conversation quickly moved beyond the book itself.At its core, this is a conversation about what it means to take your own life seriously enough to shape it into a story.Matthew didn’t set out to write a book. He started with a writing class, working through exercises, trying to figure out what he had to say. Over time, something began to emerge: a pattern connecting his love of music, his relationships, and his search for identity.The book took shape slowly, over years, through revision, reflection, and a lot of back-and-forth with his editor.The Myth of the Solo WriterOne of the more refreshing parts of this conversation was Matthew’s honesty about the writing process.There’s a common assumption that writers sit alone, produce something brilliant, and send it off into the world. That wasn’t his experience at all.His editor played a central role—not just refining the writing, but helping him discover what the story actually was.Sometimes that meant pushing him to go deeper. Sometimes it meant pulling him back. Either way, it was a collaborative process.It’s a good reminder that writing, even when it’s deeply personal, is rarely a solo act.Creativity: Inspiration vs. DisciplineMatthew’s background as a musician added another layer to the conversation.Songwriting, for him, often comes in bursts of inspiration. A melo