Navigating Midlife Transitions with Joy

Find Clarity, Purpose, and Joy in the Second Half of Life

Are You Wondering If There Is More To Midlife Than You Are Experiencing?

  • I thought I’d feel satisfied by now, but I keep wondering if there’s something more.

  • I’ve accomplished so much but I still feel like something is missing.

  • I’m tired of feeling stuck in this phase of life, unsure of how to move forward.

  • Friends and family surround me, but I still feel disconnected and unfulfilled.

  • I have time and resources but don’t know how to make the most of them.

  • I feel guilty for not enjoying this stage of life as much as I thought I would.

  • I’ve spent my whole life focused on work, and now I’m unsure who I am outside my career.

  • I’m afraid it’s too late to reinvent myself and find something I’m passionate about.

Have You Ever Found Yourself Thinking...

Imagine a Life Where You...

  • Rediscover a sense of purpose and direction.

  • Find new passions and a renewed excitement for the future.

  • Reignite your passion for your living.

  • Look forward to each day feeling fulfilled.

  • Make meaningful contributions to your next chapter.

  • Have a clear plan and actionable steps.

Empowering You to...

  • Feel motivated, energized, and confident in your daily impact.

  • Create a vibrant, meaningful life that aligns with your values.

  • Confidently embrace this transition as a time of growth and possibility.

  • Wake up every morning inspired to pursue the things that bring you joy!

  • Feel deeply connected to your purpose and know each moment is filled with intention and meaning.

  • Use your unique gifts to impact your community, loved ones, and the world.

  • Transition into midlife confidently and know precisely how to create a life you love.

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.

Because life truly does get better with age.

What our clients and readers say

  • Image of Erica Hill

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

    We have all heard the saying knowledge is power. And while we gather a lot of knowledge over the years, many of us leave our careers and have no idea how to apply that earned wisdom toward building a future.

    What tends to be missing is clarity, coupled with guidance around that knowledge. That is exactly what this workbook provides. The combination of knowledge, plus clarity, plus guidance unlocks a super power which enables us to step into our next chapters with confidence, excitement and most importantly, a plan!

    Just follow the steps to your next and best life!!

    - Erica Hill

  • Working with Holly has been a joy.

    Holly has been an incredible support as I navigate the transitions between my younger self and midlife at 54.

    She has helped me to see and deepen what is working and also to let go ways of being that no longer work.

    I encourage anyone navigating this time in life to work with Holly who can illuminate what we can’t always see for ourselves.

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

    - Guy Thompson

  • Image of Susan Tear

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

    It is a heartwarming exercise that will illuminate and open up your history, your story, and how this relates to your inspiring future self.

    It is a thorough and fun exercise of discovery that will lead you to your most fulfilling possibilities.  The final chapter, I feel as if I’m growing whole sums it up well.

    The things that we love tell us who we are - Thomas Aquinas.  This workbook develops this idea into a thorough and wonderfully provocative exercise that will help lead you to your best possibilities.  I highly recommend this illuminating journey.

    - Susan Tear

  • Holly has been an invaluable life coach

    Holly has been an invaluable life coach, guiding me through Chip Conley's "Learning to Love Midlife".  Her thoughtful exercises, organized counseling and generous heart help reveal the clearest path through the most difficult emotional and mental mid-life terrain. With her support, I’m navigating the journey with confidence and clarity, ready for whatever comes next.

    - Kevin O’Neill

Introducing The Learning to Love Midlife Workbook 

Find Your Next Path

Midlife is often humorously described as a crisis, with cliches about sports cars and radical life changes. Yet, as Chip Conley eloquently explains, midlife can be reimagined as a period of profound transformation and awakening. The "Learning to Love Midlife Workbook" takes Chip’s insights and translates them into actionable exercises, empowering you to envision a new and fulfilling future for yourself!

This workbook is designed to guide you through a series of thoughtfully crafted exercises that encourage introspection and intentionality. Each section prompts you to reflect on your values, aspirations, and the unique experiences that shape your journey. With guided prompts, you can explore what truly matters to you and how to cultivate a future that resonates with your authentic self.

Moreover, the exercises are tailored to empower you to set realistic goals and create an actionable plan for achieving them. Instead of succumbing to societal stereotypes, you are invited to redefine your narrative and embrace the possibilities that midlife offers. By focusing on your strengths and passions, the workbook inspires a profound sense of agency, allowing you to create a fulfilling life trajectory moving forward.

In essence, the "Learning to Love Midlife Workbook" supports the notion that this period can be a time of exquisite awakening.