Learning to Love Midlife: Design Your Daring Next Chapter
Is a partial scholarship for you?
We believe in making personal growth and education accessible to everyone, which is why we offer partial scholarships on a needs-aware basis for many of our programs.
These scholarships support individuals facing financial challenges, including — but not limited to — members of underrepresented communities. If financial stress might prevent you from attending a workshop, we encourage you to apply.
Partial scholarships, provided through the Association for Growth and Education, are limited to 2–3 seats per workshop and reviewed in the order received. We recommend applying as soon as possible, as scholarship decisions are typically confirmed 90–120 days before the workshop date.
Holly Prescott
Certified Life Coach | Midlife Sherpa Co-founder | Career and Life Transition Expert
Kelly White
Executive Coach | Midlife Sherpa Co-Founder | Midlife Transformation Guide
Get the expert guidance you need to stop reading about midlife transformation and start living it
You've read Chip Conley's Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age – maybe more than once. You highlighted passages and nodded along thinking, "Yes! This is what I need in my life."
You finished the book feeling inspired… but then life pulled you back into your usual routines. Work demanded your attention. Your family needed you. The days blurred together. And that sense of possibility you felt while reading faded into the background.
Months pass and you're still moving through the same patterns, wondering when things will shift. The insights from Chip’s book made sense, but without doing the work to apply them, nothing changes.
You're stuck in the gap between knowing what's possible and actually living it – and the longer you stay there, the harder it becomes to believe change is even possible.
Meanwhile, the years that could be spent enjoying your best life are slipping away.
You can't read your way into transformation. You have to do the work.
If you want to implement the insights you gained from Chip’s transformative book in an effective, sustainable way, you need structure, reflection, honest self-assessment – and the support to follow through when everything else is competing for your attention.
That's where Holly Prescott and Kelly White come in. As certified life and career coaches who have spent years working with people navigating midlife transitions, they specialize in helping people move from feeling stuck to taking meaningful action that creates lasting change.
That’s why, after reading Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, they approached Chip directly and asked for his permission to create a comprehensive workbook based on his book that was designed to help people put what they learned from the book into practice.
Chip loved their workbook so much he has wholeheartedly endorsed it – and now Holly and Kelly are coming to Santa Fe to offer people the intimate, in-person guidance and support they need to bridge the gap between knowing what's possible and actually living it.
Discover your personal “Daring Dozen” and follow a proven roadmap to embody them more fully in your life
Over three transformative days in Santa Fe, Holly and Kelly will guide you through structured exercises and reflections that help you assess where you are now across five key areas of your life: physical, emotional, mental, vocational, and spiritual.
As you explore Chip's “12 Reasons Why Life Gets Better” in depth, you'll identify which resonate most deeply with you and craft your own "Daring Dozen" – your personal list of reasons why life is improving with age, grounded in your unique values and experiences.
Here's what makes this different from reading the book alone: you'll have expert guidance to help you dig deeper, a small group of peers navigating the same questions, and dedicated time away from daily distractions to actually complete the work.
No more telling yourself you'll get to it later. No more skimming past the hard questions. Just focused, supported progress.
Whether you’ve read Chip’s book cover to cover multiple times or are only learning about it just now, you'll walk away with a personalized roadmap and a concrete action plan with clear, prioritized goals for each area of your life – and the steps to achieve them.
During your four days together, you will…
Work through structured self-assessments to identify where you are now across all five life areas – and gain clarity on where you want to go
Explore Chip's 12 reasons through guided exercises that move beyond intellectual understanding to personal application
Participate in facilitated group discussions that help you see patterns and possibilities you might have missed on your own
Set clear, measurable goals for each of the five life areas: physical, emotional, mental, vocational, and spiritual
Prioritize your goals and design a concrete action plan with specific steps, timelines, and accountability measures
Receive expert guidance from Holly and Kelly to refine your plan and overcome obstacles that have held you back
Connect with peers who are navigating similar transitions and committed to doing the work
And you’ll do this powerful work in an intimate, small-group setting surrounded by luxury and the stunning natural beauty of the Santa Fe high desert.
This Workshop
Is For You If…
Meet
Holly Prescott
Certified Life Coach | Midlife Sherpa co-founder | Midlife Transformation Guide
After four decades building a successful real estate career, Holly Prescott made a bold midlife pivot. She realized her true passion wasn't just helping people buy homes, but helping them build meaningful lives – so she transitioned into certified life coaching, specializing in guiding people through the transformative transitions of midlife.
Inspired by Arthur Brooks' From Strength to Strength and Chip Conley's Learning to Love Midlife, Holly approached Chip directly to create a comprehensive year-long coaching program and workbook based on his bestselling book. Her approach is grounded in real experience helping people move from stuck to purposeful.
As co-founder of MidlifeSherpa.com and an MEA-certified TQ™ (Transitional Intelligence) facilitator, Holly leads others on journeys of reinvention with clarity, structure, and genuine enthusiasm for what's possible in life's "fourth quarter."
Kelly White
Executive Coach | Career Transition Expert | Business Strategist
Kelly White is an executive coach and career transition specialist with over 20 years of experience guiding professionals through pivotal career and life changes. Her background spans launching national coaching platforms, scaling executive recruiting operations, and pioneering tech-driven real estate models – giving her an unusually broad perspective on how to build a life aligned with personal values and long-term fulfillment.
In 2017, Kelly became a certified life coach and created The Career Formula Program, a proven framework that helps professionals articulate their unique value and align their work with deeper purpose. She's conducted over 10,000 interviews and helped hundreds of mid- and late-career professionals successfully navigate industry transitions.
As co-founder of Midlife Sherpa and co-creator of the Workbook for Learning to Love Midlife, Kelly specializes in turning midlife uncertainty into actionable strategy – helping people design a second half of life that's both fulfilling and financially sustainable.
What You'll Gain
Your personalized "Daring Dozen" and a proven action plan
Your own list of reasons life is getting better – plus a concrete roadmap with prioritized goals and realistic timelines.
A proven framework you can use for years
Learn a structured reflection process you can return to whenever you need to recalibrate your direction.
Clarity on what you actually want
Cut through the noise and identify what genuinely matters to you, not what you think you should want.
Community and ongoing accountability
Build connections with peers who are committed to the work and will support you beyond Santa Fe.
Our Agenda at a Glance
Monday:
Tuesday:
Wednesday:
Thursday:
4:00 PM: Arrival / Check-In
5:30 PM: Welcome Reception & Dinner
7:00 PM: Orientation Session
9:00 PM: Free Time
Friday:
7:30 AM: Mind + Body
8:30 AM: Breakfast
10:00 AM: Classroom Time
1:15 PM: Lunch
2:00 PM: Free Time
3:00 PM: Classroom Time
6:30 PM: Dinner
Saturday:
7:30 AM: Mind + Body
8:30 AM: Breakfast
10:00 AM: Classroom Time
1:15 PM: Lunch
2:00 PM: Free Time
3:00 PM: Classroom Time
6:30 PM: Dinner, Dessert & Graduation
8:00 PM: Evening Gathering
Sunday:
7:00 AM: Breakfast
10:00 AM: Checkout / Departure
*Please note that not all “classroom time” activities take place in the actual classroom.
*Please note all times are estimates as some activities go longer or shorter depending on the group. This agenda is meant to give you an idea of the general flow of activities.
Step into transformation in the high desert
Rising Circle Ranch | Santa Fe, USA.
Our spectacular Santa Fe campus is located on an upscale regenerative ranch featuring traditional Pueblo architecture and nearly 2,600 acres of wildlife, hiking trails in the arroyo, and awe-inspiring beauty. Close to historic Santa Fe, an artisan’s mecca.
PLUS: Gourmet from-scratch meals, snacks, and drinks featuring locally sourced ingredients, made by our in-house chefs
Explore the ranch
on horseback
Our Rising Circle Ranch spans 2,600 acres of New Mexico high desert, offering guided horseback riding for all experience levels through diverse terrains under the vast Southwest sky
You’ll experience highlights like:
Horseback riding is an optional add-on activity you can book once you arrive on the ranch. Whether you’re seasoned or brand new to horseback adventures, this guided experience lets you discover the ranch’s natural wonders alongside our gentle horses.
Your Workshop Also Includes:
It’s time to close the gap between knowing what's possible and actually living it.
This is your chance to give yourself three powerful days to finally do the work. To stop reading about transformation and start designing it – and walk away with a concrete plan instead of another highlighted book on your shelf.
Join Holly and Kelly at Rising Circle Ranch in Santa Fe and leave with:
Your best years are ahead of you – and they start in Santa Fe.
Book your spot today
Learning to Love Midlife: Design Your Daring Next Chapter
Is a partial scholarship for you?
We believe in making personal growth and education accessible to everyone, which is why we offer partial scholarships on a needs-aware basis for many of our programs.
These scholarships support individuals facing financial challenges, including — but not limited to — members of underrepresented communities. If financial stress might prevent you from attending a workshop, we encourage you to apply.
Partial scholarships, provided through the Association for Growth and Education, are limited to 2–3 seats per workshop and reviewed in the order received. We recommend applying as soon as possible, as scholarship decisions are typically confirmed 90–120 days before the workshop date.
The program was spectacular. It really surpassed my expectations. I was really surprised about how the course was curated. There was such a warm intensity and personal touch to it.
I experienced MEA as a newly diagnosed multiple myeloma cancer patient, and as a result of the things I’ve learned - I’ve banished the anxiety of being a cancer victim, am in remission, and living with a newfound energy and purpose.
Just know how grateful I am for the joy fuel you all put in my rocket ship. When I want to feel loved or just need a good smile I can think of my time at MEA, which came at the perfect time to encourage me on my journey. Thank you!
Frequently Asked Questions
How do I know if this is the right workshop for me?
If you’re feeling depleted, disconnected, flat, or simply ready for a more intentional, meaningful next chapter – and if you resonate with the truth that life is finite and the time to feel alive is now – then this workshop is a powerful fit.
Who is this workshop for?
This experience is for anyone standing at a life crossroads or moving through a period of transition. Many participants are navigating shifts in career, relationships, health, identity, or stage of life – and are looking for tools, support, and fresh perspective to move forward with clarity and confidence.
Do I need to have read Chip’s book, Learning to Love Midlife before I attend?
No, though you will likely find the experience richer if you are already familiar with Chip’s work and his 12 Reasons Why Life Gets Better with Age. However, the workshop curriculum will walk you through all twelve chapters of his book in some detail, so you will still gain a lot if you haven’t read the book.
Do I need to be navigating a specific midlife transition to attend?
Not at all. Some participants come with a clear change they’re navigating. Others may feel overwhelmed because they’re dealing with too many transitions at once, while some others may simply feel lost and yearn for renewal. This workshop meets you where you are and helps you find direction, even in the midst of uncertainty.
Is this workshop religious or spiritual?
MEA welcomes people from all walks of life, beliefs, and backgrounds. The Learning to Love Midlife experience is science-based and non-religious, though it may invite reflection on your personal values, meaning, and what matters most to you.
What if I’m not planning a major life change?
You don’t need to be making big external changes to benefit. Many participants come seeking internal shifts: new perspective, fresh energy, or a deeper sense of alignment with the life they’re already living. This workshop helps you approach any threshold – big or small – with greater grace and intention.
What’s included in the tuition?
Your tuition includes all programming, three nights of accommodations, chef-prepared meals, snacks, drinks, and access to MEA’s inspiring campus in Santa Fe. The only additional costs are transportation to the venue and any personal incidentals.
How do I know if I qualify for a partial scholarship?
We award partial scholarships on a needs-aware basis. Our goal is to make MEA accessible to those who may face financial barriers to attending. If you’re experiencing financial stress that could prevent your participation, we encourage you to apply for assistance.
What if I’m not sure if this workshop is right for me?
We’re happy to help. Book a free call with our team, and we can help you decide based on your current life situation, goals, and timing.
Still deciding or have questions?
Connect with our helpful team of Advisors
Our Advisors are all MEA alumni who can offer genuine insights into our programs. They’re passionate about helping you finding the right fit to make your next chapter the best one.
Daniel Booz
Lucas Erie
Leslie Bartlett