Sailing into Purpose: Phoebe Rogers on Adventure, Adversity, and Transformation at Sea

In Episode 243 of the Women Offshore Podcast, Christine MacMillan sits down with Phoebe Rogers—a sailor, educator, and adventurer whose life is defined by courage, curiosity, and the call of the ocean.

Phoebe calls herself a mountain girl at heart with a sailing problem. Her love for sailing began at age 14 on Lake Tahoe, racing with her stepfather aboard a Melges 24. But that early spark evolved into something much bigger: a calling to live fully, challenge limits, and connect people to themselves and the sea.

In 2020, Phoebe made a life-changing decision. She left her job as a legal assistant to pursue sailing full-time, chasing her passion for adventure and teaching. Today, she holds both a USCG Master’s MMC and a commercially endorsed RYA Yachtmaster Offshore certification, and has worked on vessels ranging from 72-foot adventure yachts to quick little dinghies used for sail training.

For Phoebe, sailing is far more than a skill or a job—it’s a medium for personal transformation. Whether navigating through remote stretches of ocean or leading crews through challenging conditions, she finds fulfillment in helping others safely live out their wildest sailing dreams.

Her philosophy is rooted in the belief that crew work, selective adversity, and adventure have the power to connect us—to the environment, to each other, and to ourselves.

 Tune in to Episode 243 to hear Phoebe’s story of courage, transformation, and the pursuit of a life truly lived offshore.