A Crossroads Moment

For decades, Holly Prescott built a successful career in real estate, coaching professionals through business growth and leadership transitions. But after years of helping others, she found herself at a personal crossroads—ready for her next chapter.

She wasn’t just looking for a new job. She was searching for something deeper that aligned with her evolving purpose and the next stage of her life.

So, she picked up the phone and called Kelly Rae White.

A Conversation That Changed Everything

Holly had long admired Kelly’s ability to guide people through transitions. Now, as she prepared to leave real estate, she wasn’t just seeking a career shift—she was looking for fulfillment.

That first phone call turned into countless conversations. They explored what meaningful midlife transitions could look like—not just in careers, but in life as a whole.

"Midlife isn’t an ending—it’s just the beginning."

Through their discussions, one thing became clear:
✔ People need guidance to navigate midlife with intention.
✔ Traditional career coaching wasn’t enough—this was bigger.
✔ They had the experience and passion to help others through it.

The Birth of MidLife Sherpa

Their first collaboration? The Workbook for Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age—a practical guide inspired by Chip Conley’s insights on embracing midlife as a time of growth and renewal.

📖 The workbook became the foundation for what would soon evolve into Midlife Sherpa—a coaching program designed to help people enter the second half of life with:
✔ Clarity – Understanding what truly matters
✔ Confidence – Embracing change with purpose
✔ A Plan – Practical steps toward fulfillment

Now, Kelly and Holly are launching the Midlife Sherpa coaching program, combining their decades of experience in career coaching, leadership, and personal development to help others navigate midlife transitions with intention.