There is something quietly magical about a conversation that unfolds the way a good book does.
One page and in our case, one sip at a time.
For this Literary Sips Sipdown, we settled into a quiet corner at The Dan inside Tampa’s historic Hotel Flor.
The room felt built for stories and low voices.
That is where we met Robyn Ostrem, CEO of Big Brothers Big Sisters of Tampa Bay.
Her life reads like a story still being written.
Sipdown
What’s your go-to sip?
“Iced tea,” she laughed. “I’m kind of an iced-tea connoisseur. I like it brewed fresh by the glass. But if it’s cocktail time, it’s a spicy margarita. And the spicier, the better.”
An iced-tea connoisseur with a spicy margarita on standby.
A little comfort and a little fire.
What books shaped who you are?
“One of the first was a children’s book called Mr. Pine’s Purple House. Everyone else’s house was white and he painted his purple. It taught me it was okay to stand out, to be different, even when it feels scary.”
“As an adult, two leadership parables changed how I lead, The Go-Giver and The Janitor. They taught me that generosity and respect matter, regardless of what role someone has. I really do lead with a servant heart.”
What chapter of your life are you living right now?
“It feels like a very layered chapter.”
“In some ways, it’s beautiful. My husband and I moved to Tampa in 2019. He captains a tow boat now. Our two daughters are grown, one in graduate school at the University of Florida, the other a math major at Florida State.”
Her voice softened.
“And in other ways, it’s been one of the hardest chapters. In 2024, I found a lump, just months after a normal mammogram. That led to surgery, immunotherapy and a mastectomy. Now I’m in a clinical trial at Moffitt designed to help prevent recurrence.”
“My camera roll is full of women in pink gowns now. Everyone sends me their mammogram photos. It’s like this strange, beautiful scrapbook of people taking care of themselves. Detection is everything.”
Sitting across from her, I felt the quiet recognition of our unasked-for sisterhood.
My own breast-cancer detour led me to the fulfillment of a long-held dream, writing The Accidental Sisterhood, and into advocacy through Moffitt.
Our stories were different.
The truth underneath was the same.
Was there a book that helped you through your breast cancer chapter?
“A friend of mine wrote There’s No Good Book for This, But I Wrote It Anyway by Carol Lockwood. She went through breast cancer just before I did and her book is honest and real. I give it to anyone who has to walk that road.”
Any guilty reading pleasures?
“Fifty Shades of Grey! I read it. I didn’t watch the movie. Yet.”
Is there a book you couldn’t put down?
“The Many Lives of Mama Love by Lara Love Hardin. It’s a true story about a woman who loses everything and fights her way back. I couldn’t stop reading it. It reminds you that no matter how broken a chapter looks, your story isn’t over.”
Finally, if you were writing your autobiography, what would the title be?
“I Built the Plane While Flying It.”
“When my baby was little, my husband was working nights as a police officer and I was working nights at a hospital and we didn’t even know who would be watching our child. I opened the newspaper one day and saw that Big Brothers Big Sisters was hiring, so I took the leap.”
“That opportunity eventually became my first executive director role. Suddenly I was running an organization, writing grants, managing budgets and learning how to work with a board of directors, all while figuring out motherhood at the same time.”
“You don’t have everything figured out before you start. You build as you go.”
That is the note I kept thinking about as we wrapped.
Most of us build the plane mid-flight.
Ostrem has simply learned how to name it.
Learn more: Big Brothers Big Sisters of Tampa Bay at bbbstampabay.org.
