Amanda Lahr

Behind the Stories, Part IV: A Conversation with Robert Winship

In this series, we interview some of Bittersweet’s long-standing and talented contributors about the art of storytelling. Bittersweet stories are only as good as the people who tell them, so in this series, we go behind the scenes to capture a glimpse of the faces behind the faces of our stories. From what sparked their interest in the craft to what makes a good story to why they contribute, these interviews delve into the personal, the professional and the transformative. 

"Bittersweet engages with the darkness but seeks redemption and triumph." – Robert Winship

Part IV of this series features contributing writer Robert Winship. As Radio Coordinator for Arlington Independent Media, he is passionate about supporting local music and helping integrate local artists through media. He has written articles for WAMU and is a dedicated contributor to Bittersweet Monthly. Read his full interview below to learn more about Robert and his journey as a writer.

What first sparked your interest in creative writing?

RW / I became interested in creative writing mainly through poetry in middle and high school. I loved the freedom and later the many structural modes of poetry and fell in love with the works of Leonard Cohen, Louise Glück and Mark Strand. For long-form, I latched onto the more obvious touchstones of high school rebellion (Vonnegut, Hunter Thompson, etc.), but learned especially from one English teacher’s affinity for Tim O’Brien and the author’s ability to communicate a more honest emotional story though fiction rather than through biographical account.

What is your greatest challenge in storytelling?

RW / The greatest challenge in storytelling overall is to get myself out of the story. Unless I’m writing a real gonzo tale about what it’s like to be a person at an event, I want the story to reflect the people and places that it’s meant to be about. It’s also a challenge for me to edit down all the research I’ve gathered early on in the process, to organize all the information and interviews into a simple, yet deeply meaningful story.

What is the key to a compelling story? 

RW / Conflict and universal truth.

What is your favorite thing about writing? 

RW / Writing is a chore, and for a long time, I harbored the belief that someday it would be fun to’s not really. Some aspects are fun, but the routine of writing is very lonely, and I’m attracted to a more chaotic environment. What I love about writing is that when I am able to sit down and face the silence and loneliness, I’m often surprised by what comes out. Sometimes all the junk that’s been stewing in my brain comes out in an eloquent or better yet, emotionally and factually accurate way, as if produced by another being. The subtext, I suppose, is that the struggle to be solitary and conquer that loneliness is a gift and a journey.

What motivates you? 

RW / Honesty and authenticity. I want to develop genuine connections with people and am motivated by the reward of relating to and learning from new people. I like to have honest conversations, explore new ideas, joke around and forge meaningful friendships. 

Why do you contribute to Bittersweet projects?

RW / I have huge respect and admiration for the quality of the work Bittersweet produces and for each of the individuals contributing to the process.

How do you approach a story? 

RW / I usually know from an interview whether that voice is compelling and/or offers important details emotionally or factually about the subject. Overall, I’m focused on creating space for marginalized or otherwise unheard voices, which goes back to ensuring that it’s the subjects and not the author whose words resonate in the final story.

Can you describe a time when you have creatively pushed yourself through a Bittersweet project?

RW / Every one of the Bittersweet stories I’ve written has been creatively challenging because each organization has a narrative of triumph in some way, and I want to draft a story that does justice to that narrative, but also stands out and keeps readers interested and engaged.

Is there a person or character who stands out from one of the stories you have written?

RW / Tara Libert of Free Minds. She is everything you hope for in a story. She is positive, forthcoming and encouraging to everyone around her. Her openness and honesty have built a deep level of trust with the Free Minds guys, and her authenticity brings out strong reactions. I benefited from that openness. She was like a story Sherpa – I just followed along a wrote everything down.

What is unique about the Bittersweet storytelling process?

RW / Bittersweet engages with the darkness but seeks redemption and triumph. This is not completely unique as an idea, but as a mission, it’s rare. The astounding skill of Bittersweet’s visual and back-end team is what makes the process truly shine. I could write anything, and the story is 75% better because of visual presence and interactivity of the platform. 

Up Next

Tune in next week for Part V in this series – an interview with Bittersweet Monthly Managing Director and filmmaker, Dave Baker.