Holly Prescott

After four decades in the real estate industry—including owning three Keller Williams franchises and serving as a Master Faculty Trainer—Holly Prescott realized her true passion wasn’t only selling homes, but helping people grow. With over 3,600 coaching calls and 800 seminars under her belt, she transitioned into a new chapter as a Certified Life Coach, specializing in guiding people through the often-overlooked transitions of midlife. Inspired by Arthur Brooks’ From Strength to Strength and Chip Conley’s Learning to Love Midlife, Holly created a year-long coaching program and workbook to help others navigate this powerful life stage with clarity, confidence, and renewed purpose.

Holly is the founder of MidlifeSherpa.com, leading others on a journey of reinvention—encouraging curiosity, skill-building, and community. She completed MEA’s Navigating Transitions certification, been trained as a TQ Coach, and remain deeply involved in the MEA community, presenting workshops and promoting the message that “life really does get better with age.” Whether on the slopes, on the golf course, or in coaching sessions, Holly is living proof that the “fourth quarter” can be the most rewarding—and she’s here to help others do the same.