Sibling Collaboration at 30,000 Feet:

Writing partnerships require respect, trust, and vulnerability. Anna Schmidt shares the highs and lows of co-authoring with her brother, revealing how respect, trust, and a dash of humor turned turbulence into a memoir that soars on honesty and connection.

The Flight to Collaboration

Siblings are better known for clobbering than collaboration. So when my oldest brother, Donald, approached me about writing a book together, I wasn’t sure how to react.

We’d just survived one of the worst years of our lives. Within nine short months, we lost a sister to cancer, buried our elderly mother, and experienced the horror of our nephew’s sudden death in a car crash.

Was I even emotionally healthy enough to take on a massive writing project?

The answer: definitely not.

But Donald has one of those persuasive personalities. He’s a finagler. Filled with big ideas, optimism, and enthusiasm, it’s hard not to get swept up in the tailwinds of possibility. And as the youngest sibling in the family, it’s hard for me to say no.

Before I could fully comprehend what I was getting myself into, I was typing the first chapter of what would become Where We Land: A Pilot’s Reflections at Altitude, a memoir of flight and a humorous look at the underbelly of the aviation industry. I had no idea I was about to learn a lifetime’s worth of lessons on collaborative writing.

Not all siblings could, or even should, form a writing partnership. As any author knows, writing is a vulnerable process. It can make you question your self-worth. On bad days, writing can be a debilitating, soul-crushing experience.

Not exactly something you want to subject yourself to with the wrong person.

So what makes a good writing partner? Similar styles? A shared sense of what makes a great story? An agreement on the Oxford comma?

Respect at the Core

For Donald and me, one thing surpassed everything else in making our partnership work: a true respect for each other’s areas of expertise. If you’re considering a co-authoring project, make sure it’s with someone you genuinely admire. Writing a book with someone you don’t fully respect, or who doesn’t fully respect you, is unlikely to succeed.

Before writing this book, I knew next to nothing about the airline industry. And Donald, though a natural born storyteller, knew nothing about the writing and publishing process. Writing together required not only respect, but trust.

And no one had to trust more than Donald.

Memoir Isn’t Fiction

Memoir hits a little differently than fiction. Fiction allows a writer to explore pain and fear in the guise of character development and plot lines. A memoirist lays it all bare. When writing your life story, the sting of a father’s abandonment can’t masquerade as the cause of the villain’s poor decisions. These are feelings you have to claim as your own on the page. Memoir requires a willingness to be honest, even when it’s uncomfortable. That honesty is what readers connect to.

Our situation was unique in that I was able to use my brother as a shield. In the writing of my brother’s most vulnerable moments, I had no choice but to face my own. Though we shared similarities in our upbringing, birth order precluded very different life experiences, something I didn’t comprehend before beginning this work.

Trusting Each Other—and the Reader

Donald trusted me with his life. He gave me the freedom to sort through his mistakes, weaknesses, and at times, unflattering portrayals. He allowed me to make the decisions about what should go on the page and what should remain untold.

And then Donald trusted the readers.

When you publish stories about real people and real situations, you have to be prepared for feedback from those same real people who were in those real situations.

That takes bravery.

Donald placed his confidence in me and bestowed our readers with truth. Sometimes the truth was gritty, usually it was hilarious, but sometimes it was heart-wrenchingly sad.

These unfiltered glimpses into human pain struck a chord. The reviews and comments kept coming in. Though many of Donald’s stories were particular to the airline industry, readers grasped onto the universal undertones present within the book.

As a non-aviator writing from the perspective of a seasoned pilot, I had no choice but to write from a place of understanding. This required hours of research and endless phone conversations. Writers tackling unfamiliar territory should never underestimate the time it takes to get the details right. Though I’d known my brother my whole life, it took writing a book together before I really understood him. Perhaps that’s part of why the book resonates.

More Than Airplanes

We thought we were writing about airplanes. It turns out we were writing about persistence, resilience, and connection. In writing this book, I learned more about my brother, my family, and myself than I ever expected. Grief has a way of unmaking you, but storytelling gave us a way to piece things back together.

Writing Where We Land wasn’t just about telling my brother’s story. It was also an opportunity for me to come to terms with our year of loss. Somewhere between edits and revisions, laughter and grief, we found healing. Maybe the greatest surprise was not where we landed, but who we became on the journey.

I entered this project as a grieving sister, but I left it as a more courageous writer.

ABOUT THE AUTHOR

Anna Henkens Schmidt lives in North Carolina with her husband, where she homeschools their three children and pursues her passion for writing. She began her publishing journey by collaborating with her brother, Donald Osborn, to release Where We Land: A Pilot’s Reflections at Altitude. The success of that memoir led to two more books from the sibling duo: Where We Land: A Boy, a Plane, and a Dream, a fully illustrated children’s story that encourages kids to keep reaching for the sky, and their latest release, The Ding Dong Altar Boy, a laugh-out-loud collection of true tales from small-town life that proves real stories really are stranger (and funnier) than fiction. Anna is currently hard at work on a new novel, slated for publication in 2026.

Website: https://www.annahenkensschmidt.com/
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THE DING DONG ALTAR BOY

The Ding Dong Altar Boy is a laugh-out-loud collection of true stories from the heart of western Nebraska. Growing up in a small town meant inventing your own fun-and Donald Osborn’s memoir captures the wild, messy, and hilarious adventures that come with it.

From driving a car down the hallways of his high school (on purpose!) to leaping over a corpse mid-run, these tales serve up the kind of chaos you couldn’t invent if you tried. Ever sneaked into a drive-in with a trunk full of friends? Worked at a local radio station where everything falls apart? Or convinced an entire college that Neil Diamond’s wife was roaming campus incognito? If so, you’re in the right place.

Along the way, meet unforgettable dogs, endure a meltdown at Spaghetti Works, and narrowly sidestep a falling tree. Whether it’s demolition derbies, wrangling forest fires, raising kids, or making gloriously bad decisions on the backroads of rural America, these stories throw you headfirst into the wild comedy of growing up in the Midwest.

Perfect for fans of personal memoirs, small town life, rural Americana, and humor, this book brings to life the unpredictable and often ridiculous moments of a childhood spent on dusty country roads. If you love stories that feel like legendary bar chatter, The Ding Dong Altar Boy is calling your name.

Grab a drink, settle in, and get ready for a rollercoaster of mischief, mayhem, and heartfelt reflection from the plains of Nebraska.