The MidLife
Sherpa Story
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 Crossroads Moment
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.
A Conversation
That Changed Everything
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.
Maybe Being “Over-The-Hill”
is a Good Thing?
In the 1950s, the term "over-the-hill" became popular as a humorous way to describe turning 50, but it’s time to rethink that. Instead of seeing it as an end, it’s a moment of achievement. Climbing the hill in your 20s, 30s, and 40s might be challenging, but once you reach the top, the view becomes clearer, and the journey downhill is much easier.
I asked ChatGPT to write me a poem about the upside of being over the hill:
They call it "over the hill," as if it's a fall,
But from this height, I can see it all.
The winding paths, the roads I’ve climbed,
Each step a verse in a life well-rhymed.
The air is clearer, the noise fades away,
Wisdom’s glow lights the end of each day.
The pace may be slower, but the view is divine,
A landscape of moments that shimmer and shine.
So here on the summit, I pause, fulfilled—
Being "over the hill" is the dream I’ve built.
— Chip
Check out the full article and learn more about embracing midlife with intention and purpose!