The Heart of Midlife Sherpa:
Meet the Founders
Coach | Leadership Expert | Midlife Guide
Holly Prescott has dedicated her career to guiding individuals through transformative life stages. With a leadership, coaching, and personal development background, she has helped countless professionals find clarity and direction in times of change.
A pivotal moment in Holly’s journey was attending the Modern Elder Academy, founded by Chip Conley, where she deepened her understanding of midlife as a period of growth and renewal. This experience, combined with her certifications as a Life Coach and in Transitional Intelligence (TQ), equips her with specialized tools to support individuals navigating major life and career transitions.
💡 Her Philosophy:
"Midlife is not about reinvention—it’s about rediscovering what truly matters and aligning your life accordingly."
Her passion for this work led her to collaborate with Kelly Prescott to co-author the Workbook for Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, and she is the founder of Midlife Sherpa. Through their work, they are on a mission to help others embrace this stage of life with confidence and a sense of curiosity.
Holly Prescott
Executive Coach | Business Strategist | Career Transition Expert
Kelly has built her career on innovation, strategy, and helping people navigate pivotal transitions. After years of leading groundbreaking initiatives in real estate—launching national coaching platforms, scaling executive recruiting programs, and pioneering technology-driven brokerage models—she turned her focus to what truly lights her up: guiding individuals through life’s biggest transitions with purpose and clarity.
As a certified life coach since 2017, Kelly founded The Career Formula Program, a proven framework designed to help professionals successfully navigate career transitions and job searches. With over 20+ years of experience and over 10,000 interviews, she deeply understands how to align talents with meaningful opportunities.
💡 Her Perspective:
"Midlife isn’t a time to slow down—it’s a time to confidently step into a new, exciting phase."
Inspired by this mission, Kelly partnered with Holly Prescott to co-author the Workbook for Learning to Love Midlife and co-founded Midlife Sherpa, helping others navigate this season of life with clarity, purpose, and joy.