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Writing Personal Essays from Our Most Reckless Days: an Interview with Samantha Mann
by Writing Workshops Staff
4 days ago
Samantha Mann has spent her career untangling the threads of identity, culture, and memory. As a celebrated writer whose work has graced the pages of Vogue, The Cut, and Washington Post Magazine, Samantha has an unparalleled gift for transforming personal experiences into stories that resonate on a universal level. Her essay collection, Putting Out: Essays on Otherness, captured the hearts of readers everywhere, while her anthology, I Feel Love: Notes on Queer Joy, has been hailed as a landmark celebration of LGBTQIA+ voices. Now, with her sophomore collection Dyke Delusions, slated for release in June 2025, Samantha is opening the door to her creative process in an exclusive four-week workshop at WritingWorkshops.com.
In this engaging interview, Samantha delves into the transformative power of exploring our past to uncover the stories that define us today. She shares insights from her own journey, revealing how childhood memories, awkward teenage moments, and the places that shaped us can be transformed into powerful personal essays.
For aspiring and seasoned writers alike, Samantha’s workshop offers a unique opportunity to learn from one of the most dynamic voices in contemporary literature. Over four weeks, participants will gain tools to turn raw memories into polished narratives, hone their storytelling skills, and develop a deeper understanding of how personal history intersects with broader cultural contexts. With a syllabus featuring Zadie Smith, David Sedaris, Jaquira Díaz, and Melissa Febos, this course promises to enrich your craft and leave you with three compelling essay drafts—and the confidence to pitch them for publication.
Whether you’re writing for yourself, your readers, or the world, Samantha’s workshop is your chance to unearth the stories only you can tell. In this interview, we’ll explore her creative philosophy, her advice for overcoming writing blocks, and why she believes revisiting the past can illuminate the path forward.
Writing Workshops: Your course is titled My Misspent Youth. How does tapping into our more reckless, perhaps embarrassing experiences help us produce powerful, resonant personal essays—and why did you decide to focus on that period of life for your workshop?
Samantha Mann: I find people are often excited to write and share about their youth. This time of our life is far enough away that it allows people to feel more comfortable writing about more difficult or extremely embarrassing times while having a good amount of emotional distance. Writing about an experience you can almost always then tie to who the person you are today, which makes a great entryway for other stories or connections about a writer’s current life.
WW: You’ve written extensively about queer joy, cultural commentary, and motherhood. In what ways do you see “queer joy” and “misspent youth” intersecting? Does celebrating one’s younger, wilder self inform your perspective on living authentically today?
SM: It depends on the angle you take. For many queer folks, me included, my youth was peppered with tiny moments of queer joy- flashes really- that were then moments that reinforced being closeted, feeling shame, etc. Writing explicitly about being a queer child or teen doesn’t feel particularly joyful for me as I worked hard to separate myself from that truth.
WW: When we write about past missteps or impulsive decisions, shame often lurks in the background. How do you guide students to lean into these moments rather than shy away from them? What’s your approach to turning shame into a meaningful story?
SM: I often ask students what types of personal essays they enjoy reading, and often, people feel most connected to a story when a writer is raw, honest, and unflinching and reminds them that they can’t be that for someone else if they censor their story. I also like to ask them if they ever read anything they thought a writer shared too much- and it’s almost never a no. We are much harder on ourselves than others.
WW: Your essay collection, Putting Out: Essays on Otherness, is often praised for its raw honesty. How do you help students balance preserving their privacy and “going there” on the page? Is there such a thing as sharing too much?
SM: No, and I often find that when a writer wants to leave out something of their story, it is usually the most powerful and important part. There is a misconception that essayists must be open books all the time. I am relatively private. When I write, I get to decide what story to share and how I want the story told. No one is forcing essayists to write. There is no point in telling a story if you’re going to tell it half ass.
WW: You’ve curated and edited anthologies that celebrate the richness of diverse voices. What do you hope students discover about their voices when they mine their past for essay ideas? Are there particular themes or creative risks you encourage them to explore?
SM: The outside world is very scary, so first and foremost, I want to foster a class space where students feel comfortable taking risks, knowing there is no judgment or expectation from the class. Building a supportive environment for students to explore and start building some confidence is key.
WW: David Sedaris’s "Big Boy" is a prime example of turning an uncomfortable adolescent memory into comedic gold. Why is humor such a potent device for personal essays, and how might it serve writers grappling with heavier, more sensitive subject matter?
SM: Humor is tricky. It’s a great way to ease tension and highlight the absurdity of an experience, but you don’t want to overdo it and take away from the truth of your story.
WW: Finally, your sophomore collection Dyke Delusions is forthcoming in 2025. Did any ideas in that book originate from the kind of reflective exercises you teach in this workshop? And how can students use that same process to refine their material into future projects?
SM: Yes! I often think of a letter of recommendation to generate ideas if I’m feeling stuck. Not that I will write the idea in that exact format, but it helps me find what specific routines, tangible things, and ideas I hold dear in my life that could be worth exploring deeper.
Avoid the waitlist and sign up for Samantha Mann's upcoming class: My Misspent Youth: Writing Personal Essays from Our Most Reckless Days.
Instructor Samantha Mann is a Brooklyn-based writer covering queer life, popular culture, mental health, and motherhood. She is a contributing writer for Vogue and The Cut. She has written for Elle, Today Show, Huffington Post, Bon Appetit, Bustle, Washington Post Magazine, Romper, BUST, and others. Her essay, "The Orgasm Gap and DJ Khaled," was featured in Roxane Gays newsletter, The Audacity. Samantha is the author of the essay collection, Putting Out: Essays on Otherness. In 2023 Putting Out was added to CLMPS recommended reading list for Women's History Month. Samantha edited and curated the anthology, I Feel Love: Notes on Queer Joy. And Buzzfeed Book review said, "This is the perfect collection for readers looking to appreciate and celebrate the many talented writers within the LGBTQIA+ community." Her sophomore collection, Dyke Delusions, debuts June 2025 with Read Furiously.
