The Trouble with Wings is a deeply honest and stirring memoir told with lyrical prose and unflinching honesty about a woman who, in learning that every wild choice comes with a reckoning, learns to trust herself. 

One year into a solo journey around the world, Jillian Bright was finally chasing the writing career she’d dreamed of for years—traveling, photographing, and collecting stories along the way. Then her backpack was stolen, along with two book manuscripts and a hard drive full of writing and photography. Three weeks later, she found out she was pregnant after rekindling a love affair with a man she hadn’t seen in four years.

Staring down a future she never saw coming, and certainly never saw herself wanting, Jillian retraces the choices over the last decade that led her to that moment: from designing custom bikinis in a bohemian beach town in Costa Rica to living off-grid in the mountains of Northern California to hiking to sacred lakes at 15,000 feet in the Himalaya and more… 

Through heartbreak, risk, romance, and reinvention, she began to understand what her years of wandering had really taught her—not how to escape life, but how to meet it head-on. 

The Trouble with Wings is about the freedom that comes from living with your heart wide open and the responsibility that comes with it. Because once you’ve known that kind of perspective, you can’t un-know it. And eventually, she began to understand what those years had taught her and what it means to stand at the edge of your old life, ready to claim a new one. 

For any woman who’s ever felt stuck or afraid to make the wrong choice, this is a story about having the courage to make mistakes—and the heart to let them shape you.