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 books The Big Takeaway Telling 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 chronology Quote to Ponder “I really do want to make a statement about how I see my life and what happened.” When Your Life Becomes the Material In 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 Writer One 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. Discipline Matthew’s background as a musician added another layer to the conversation. Songwriting, for him, often comes in bursts of inspiration. A melody appears. Lyrics follow. The song almost writes itself. Writing a book, on the other hand, requires something different. It’s less about waiting for the moment and more about creating the conditions for progress—sitting down, doing the work, and continuing even when it feels like a chore. There’s a parallel here to almost any meaningful work. The initial spark matters. But what carries it forward is discipline. Humor as a Path to Truth The humor of life is one of the defining features of Matthew’s memoir. Even in moments that are awkward, painful, or deeply personal, there’s often a thread of self-deprecation or wit running through the story. Humor, in this case, becomes a way of telling the truth without becoming overwhelmed by it. It creates space for both the writer and the reader to engage with difficult material. The Risk of Being Honest At some point in the process, Matthew realized he was going to publish something very revealing. The real challenge of writing such a book lay not in the act of writing itself, but the decision to let other people see it. Memoir raises a question that most forms of writing avoid: How honest am I willing to be in public? For Matthew, answering that question required a kind of courage he hadn’t needed before. Identity in Unexpected Places The connection between Matthew’s Jewish identity and his love of bluegrass music honestly surprised me. At first glance, those two might seem unrelated. But as he described it, they deeper connections in shared musical structures, emotional tones, even cultural overlaps. It reminded me that identity isn’t always as straightforward as we assume. Sometimes it shows up in places we wouldn’t expect. What This Conversation Leaves Me With If there’s one thing I keep coming back to after this conversation, it’s this: Your story doesn’t have to be extraordinary to matter. But it does have to be honest. And honesty—real honesty—takes work. It takes reflection. It takes revision. And sometimes, it takes someone else helping you see what you’re actually trying to say. * What part of your own story have you been hesitant to tell—and why? * Do you think you could write your life honestly, or would you hold something back? * Where in your life have you seen discipline matter more than inspiration? Respond to these and other ideas in the comments. If you get value from the show, consider supporting us in one of the following ways. You can make a one-time contribution or sign up for regular support through Buy Me a Coffee. You can also subscribe on Substack for free OR upgrade to a paid subscription. Your support helps me continue helping you and others, and thank you in advance! All subscribers now receive the following: * The “Big Takeaway” * A bulleted summary of the episode * Practical tips from the episode * A quote to ponder * Prefer text? We turn each podcast into an article. Plus, Founding Members receive ebook copies of all my books as well as a sponsorship message on the podcast at least once a month. That’s our way for saying “thanks for the support!” King's Chronicles is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit kingschronicles.substack.com/subscribe
