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Midlife with Joy

Find Clarity, Purpose, and a Plan

Midlife Isn’t A Crisis—It’s An Opportunity.

Get the guidance, tools, and support to create the next chapter on your terms.

You’ve built a life, a career, and relationships but now, you’re asking yourself: ‘What’s next?’

You want more than just ‘getting through’ midlife. You want to thrive. But it’s hard to know where to start between career changes, shifting relationships, and more profound questions about life’s meaning.

What’s Next?
You’re Not Alone..

Midlife Sherpa helps you:

1. Clarify what you want in this stage of life.
2. Overcome the doubts and fears holding you back.
3. Build a plan to turn uncertainty into action.

Maybe your career doesn't excite you like it used 
to—or unexpected changes have thrown you off course.

Maybe your relationships are evolving: your kids are growing up, your marriage is changing, or you're navigating life after divorce.

Maybe you're noticing subtle shifts in your energy, health, or how you see the world.

  • And with all of that...

  • You might feel stuck.

  • Uncertain.

Like you should have it all figured out by now.
You might be asking yourself:

  • “Is it too late to make a change?”

  • “What if I fail?”

  • “Is anyone else feeling this way?”

We call this what it is: Midlife Transition.


Not a crisis. Not the beginning of the end. Just a shift. But society tells you to either settle in or accept the decline.

That’s not the only path—and you deserve more.

That’s Where Midlife Sherpa Comes In.

We're here to help you navigate this transition with clarity, courage, and a sense of possibility.
Because midlife isn't the end of the road, it's the start of a new chapter—on your terms.

Why Does Midlife
Feel So Uncertain?

At Midlife Sherpa, we help people navigate this transition. We understand what you’re going through—and we know how to help. With expert guidance, community support, and practical tools, we’ll help you move from uncertainty to clarity.

You Don’t Have to
Figure This Out Alone.

Midlife Coaching

A Coaching Program for Your Midlife Journey

Midlife coaching is a transformative process designed to help individuals navigate the unique challenges and opportunities of midlife with clarity and purpose.

The MidLife Sherpa Coaching Program is designed to help you navigate the challenges and opportunities of midlife with clarity, confidence, and purpose.

Using the Learning to Love Midlife Workbook as a foundation, our coaching provides practical tools and personalized guidance to help you rediscover your passions, explore new possibilities, and thrive in the second half of life.

This transformative process empowers you to embrace midlife as a time of reinvention and growth, helping you craft a fulfilling path forward.

Explore all five areas by taking small steps in each.
Pay attention to how you feel, what comes naturally, and what feels off.
The goal isn’t to fix everything — it’s to understand where you are and what you need most right now.

A Simple Plan to Move Forward

Improve Your

Physical Life

Reinvent Your

Vocational Life

Renovate Your

Mental Life

Reset Your
Emotional Life

Reinvigorate Your
Spiritual Life

Choose What Matters Most Right Now
After exploring each area, choose the one that feels most important to focus on.

Real Stories,
Real Transformations

Midlife Sherpa isn’t just a program—it’s a turning point.

Here’s how real people moved from stuck to thriving.

  • “Her considerate and perceptive coaching has taken my understanding of what is possible to the next level and I’m incredibly grateful.”

    Guy Thompson

  • “The workbook for Learning to Love Midlife is an easy to follow, step-by-step roadmap to your perfect life.”

    Erica Hill

  • “Holly has been an invaluable life coach, with her support, I’m navigating the journey with confidence and clarity, ready for whatever comes next.”

    -Kevin O’Neill

  • “The Learning to Love Midlife Workbook is provocative and progressive in the best sense of the words.”

    Susan Tear

Your Best Years Are Ahead

Imagine waking up with clarity, confidence, and a sense of purpose. You’re no longer stuck—you have a clear plan and you’re thriving.

This is midlife reimagined:

  • Passion reignited

  • Clarity gained

  • A life aligned with what truly matters

Midlife isn’t the end—it’s your new beginning.

Introducing The Learning 
to Love Midlife Workbook 
Find Your Next Path

Midlife isn’t a crisis—it’s an opportunity. Inspired by Chip Conley’s insights, this workbook helps you reimagine this chapter as a time of transformation and growth.

Through guided prompts and thoughtful exercises, you'll reflect on your values, explore what truly matters, and chart a course toward a more fulfilling future. Rather than buying into tired stereotypes, you’ll gain the tools to embrace your unique path with clarity and purpose.

The Learning to Love Midlife Workbook is your companion for creating a life that aligns with who you are—and who you're becoming.