The 2026 Guide to Midlife

Top Coaches, Books, Podcasts & Retreats A curated resource list for the second half

Navigating the transition to a meaningful second act requires more than just "intuition"; it demands a toolkit.

This page serves as the definitive 2026 Guide to Midlife, curated for accomplished individuals - from executives to professionals, from academics to practitioners, from dedicated parents to retirees - who are ready to design their next chapter. Below, you will find a rigorously selected ranking of the Top 10 Midlife Coaches, along with essential midlife books, midlife podcasts and transformational retreats.

Unlike generic wellness lists, this guide focuses on actionable strategy, distinct purpose, and deep reinvention. Whether you are seeking a career pivot, navigating the empty nest, or looking for a profound personal reset, these resources provide the roadmap to ensure your second half is even more exhilarating than the first.

Download the 2026 Guide

Part 1: The Strategy

The Top 10 Midlife Coaches

Ranked by specialization: Strategy, Wisdom, and Wellness.

Coach	Best For...	The Approach
1. Federico Malatesta Book Strategy Call → Visit Website →	Bespoke Personal & Professional Transformation	Executive and transformational coaching for individuals in midlife who are not seeking "change," but structural clarity. Rooted in narrative theory, neuroscience, and psychoanalytic thought, the work focuses on redesigning internal architecture so decisions and direction regain coherence over time.
2. Alana Kirk Visit Website →	Self-compassion	Alana’s gentle, reflective conversations support midlife women through change, grief, and renewal, emphasizing self-compassion, meaning, and steady personal integration over time.
3. Barbara Waxman Visit Website →	Middlescence	Barbara coined the term "Middlescence" (like adolescence, but for 50s). Her coaching focuses heavily on energy - how to stop leaking it and how to harness it for a longer career.
4. Suzy Rosenstein Visit Website →	Regret-Proofing	Suzy helps professional women in their 50s and 60s get unstuck and clear about what they want.
5. Sara Smeaton Visit Website →	Intuitive Reconnection	Sara uses a "Feelings Detective" approach. If you are burned out and numb, she helps you reconnect with what you actually like before you make a business plan.
6. Allison Task Visit Website →	Transition with Humor	Allison is a choach who helps you laugh at the absurdity of midlife. She is action-oriented but brings a lightness to the heavy lifting of changing careers.
7. Dr. Keith Witt Visit Website →	Relational Maturity	A clinical psychologist, Dr.Witt works extensively with midlife men around relationships, identity, and purpose.
8. Stacy M. Lewis Visit Website →	Midlife Revolution	Stacy focuses on the unique intersectional challenges of aging, race, and career ceilings. A powerful advocate for reclaiming power in the second half.
9. Shannah Kennedy Visit Website →	Life Planning	Shannah is a master planner. She treats your life like a business project, with clear KPIs for health, wealth, and downtime.
10. Shelley McIntyre Visit Website →	Leaving Corporate	Shelley's "Burn the Map" philosophy is for the corporate VP who wants to launch a business but is terrified of losing the steady paycheck.

Part 2: The KNOWLEDGE

Top 10 Essential Midlife Books

The intellectual knowledge required to re-design your life.

Book & Author	Best For...	The Big Idea
Midlife: A Philosophical Guide Kieran Setiya View on Amazon →	Regrets Navigation	Setiya examines midlife through analytic philosophy, explaining why regret, frustration, and the sense of life’s finitude often surface at this stage.
Halftime Bob Buford View on Amazon →	Success to Significance	Midlife is a pivotal pause in which accomplished professionals reassess the trajectory of their lives and shift from achievement-driven goals to service-oriented purpose. The book blends personal narrative and executive coaching insights.
Transitions William Bridges View on Amazon →	Stages of Change	A Classic. Bridges presents a foundational model of psychological transition, arguing that every change unfolds through three internal phases: Endings, the Neutral Zone, and New Beginnings.
Finding Meaning in the Second Half of Life James Hollis View on Amazon →	Depth Reckoning	Hollis argues that the second half of life requires a fundamental psychological shift: moving from externally inherited roles to an inner, adult dialogue with one’s own fears, desires, and unfinished tasks.
Better with Age Alan D. Castel View on Amazon →	Selective Wisdom	The book distills decades of cognitive aging research to show that memory, decision-making, and wisdom can improve with age, provided people engage strategically with attention and meaning.
Life, Part Two David Chernikoff View on Amazon →	Spiritual Renewal	Chernikoff blends contemplative practice and psychology to argue that later life can be a period of deepened presence, service, and spiritual expansion.
Why Life Speeds Up as You Get Older Douwe Draaisma View on Amazon →	Time Compression	Draaisma explores why subjective time accelerates as we age, drawing on psychology, neuroscience, and autobiographical memory.
Life Reimagined Barbara Bradley Hagerty View on Amazon →	Purpose Reset	Hagerty argues that midlife is not a crisis but a developmental inflection point rich with possibility, supported by neuroscience, psychology, and personal narratives.
Midlife Maze Janis Clark Johnston View on Amazon →	Transition Mapping	A structured developmental framework for navigating the psychological transitions of midlife, emphasizing identity shifts, relationships, and life direction.
The Upgrade Louann Brizendine View on Amazon →	Menopause Renaissance	Brizendine reframes menopause as a neurological and psychological renewal, presenting evidence that the female brain becomes more focused, resilient, and purpose-driven in midlife.

Part 3: The INSPIRATION

Top 10 Midlife Podcasts

What to listen and download.

Podcast & Host	Best For...	Focus
Wiser Than Me Julia Louis-Dreyfus Listen on Apple → Listen on Spotify →	Smart Treat	Julia interviews iconic women (Jane Fonda, Isabel Allende) about aging. It’s funny, profane, and deeply comforting.
ReThinking Adam Grant Listen on Apple → Listen on Spotify →	Revealing	The world’s most famous organizational psychologist believes that great minds don't think alike; they challenge each other to think differently.
The Drive Peter Attia Listen on Apple → Listen on Spotify →	Healthspan	Hardcore longevity science. For the data-driven midlifer who wants to know exactly which blood markers to track.
Midlife Chrysalis Chip Conley Listen on Apple → Listen on Spotify →	Regenerative	Interviews on profound midlife transitions from the founder of MEA.
Midlife Matters Marie Perrigo Listen on Apple → Listen on Spotify →	Ad Hoc	A raw, honest look at the messy parts of this stage: aging parents, changing bodies, and empty nesting.
The Second Act Kerry Hannon Listen on Apple →	New Life	Features stories of people who made radical career changes after 50. Pure "proof of concept" for the fearful.
Ten Percent Happier Dan Harris Listen on Apple → Listen on Spotify →	Relax	Meditation for fidgety skeptics. Hosted by a news anchor who had a panic attack on live TV. Relatable for executives.
Mid-Career Change Mark Crossfield Listen on Apple → Listen on Spotify →	Niche	Focuses purely on the mechanics of changing jobs after 15+ years in one sector.
Second Life Hillary Kerr Listen on Apple → Listen on Spotify →	Pivots	Very high production value, with inspiring stories of female founders.
Retire with Purpose Casey Weade Listen on Apple → Listen on Spotify →	Money	Financial + Psychological. Addresses the financial side of retirement, which is the #1 fear for most people.

Part 4: The eXPERIENCE

Top 10 Midlife Retreats & Summits

Where to go when you need to pause, reset, and reimagine.

Retreat & Location	Best For...	The Vibe
1. The Artha Ranch 📍 Perrin, TX (Launching 2Q 2026) Contact for waitlist →	Bespoke Personal & Professional Transformation	The Transformation. A one-day bespoke retreat to deliberately redesign the second half of adult life. A disciplined space for widening perspective, reworking core assumptions, and making consequential choices about direction, responsibility, and meaning. Equine Coaching and classical Hatha Yoga experiences available on request.
Harvard ALI 📍 Cambridge, MA Visit Website →	Social Impact	The Fellowship. A year-long academic deep dive for C-suite leaders who want to transition from corporate success to global problem solving.
Canyon Ranch 📍 Tucson, AZ Visit Website →	Medical Reset	The Body Fix. If you need to physically reset before you can mentally pivot. Comprehensive medical, fitness, and nutritional overhaul.
Modern Elder Academy 📍 Baja, Mexico Visit Website →	Midlife crises	The Wisdom School. MEA workshops help people in midlife find the clarity, inspiration, and fulfillment they crave, in a beachfront campus.
Esalen 📍 Big Sur, California Visit Website →	Community	Human potential. Holistic retreat in the epicenter of the human potential movement. Gorgeous location.
Chief 📍 Various Visit Website →	Women Executives	Executive Network Chief is a community of ambitious women executives shaping the new area of leadership. Community and Programs.
1440 Multiversity 📍 Scotts Valley, California Visit Website →	Creating Hope	Transformative Experience Retreat center and learning destination for leadership and wellness.
Sadhguru Academy 📍 Coimbatore, India Visit Website →	Yogic Insight	Business Spiritual. 4 days leadership intensive to explore the science of scaling up one’s business and one’s self.
Hoffman Process 📍 San Rafael, California Visit Website →	Changing Patterns	Deep Enquiry. week-long retreat to change patterns conditioned in childhood.
Aro-ha 📍 Southern Apls, New Zeland Visit Website →	Immersive Experience	Nature Focused. Evidence-based adventures that transform your state of wellbeing.
Mandali 📍 Piedmont, Italy Visit Website →	Personal Time	Luxury Relax. Restorative retreats, for those seeking to connect to themselves, at a flexible pace.