Not Can I afford to retire? That sounds like a financial-planning question.
I mean: What does it cost to age here?
Housing. Healthcare. Someone to help around the house. A meal out with friends. Transportation when you no longer want to drive. And perhaps most importantly, the ability to remain socially connected without spending a fortune doing it.

For a growing number of Americans, the answer is leading south.

Mexico is already the most popular foreign country for Americans living abroad. Estimates vary because many Americans live there part-time or aren’t counted as formal residents, but commonly cited estimates put the U.S.-citizen population in Mexico well above one million.

Why Mexico?

Start with money. Depending on where and how you live, a couple can live comfortably in many Mexican communities for roughly one-third of what they would spend in a comparable place in the U.S. Private healthcare can also cost dramatically less than in the U.S.; one current retirement guide estimates healthcare costs are often 50-75% lower and many of the physicians trained in the U.S. so the quality of care is surprisingly good.

But I think something deeper is happening.

Mexico can offer something that’s becoming surprisingly expensive in America: a human-scale life.
Walkable towns. Plazas. Multigenerational families. Neighbors who know one another. A culture where aging isn’t automatically outsourced to an institution and where social life doesn’t always require an appointment on your calendar.

Of course, Mexico isn’t paradise. Language matters. Immigration rules matter. Safety can be an issue where cartels are prevalent (thankfully, Baja Sur where MEA is located is very safe). And moving somewhere because margaritas are cheaper is probably not a longevity strategy.

But Mexico raises an intriguing question.

We spend decades asking, “How much money do I need for retirement?”
Maybe that’s the wrong question.
Perhaps we should be asking:
“Where can I create an affordable sense of belonging while curating a culturally-rich life?”

Book a workshop at MEA Baja this fall or winter as a means of taste-testing what this would be like as the Baja Sage community of 26 townhomes, created by my cofounder Jeff Hamaoui, still has a few homes available for sale or rent (learn more at MEA Homes). In terms of workshops, check out our resident shaman Saul’s one-time-only program Oct 5-10 called “Become Your Own Shaman: Trust What Spirit Already Knows” or my cofounder Christine Sperber’s classic “Navigating Transitions” workshop Oct 19-24. It’s a lovely time of year to be in Baja: warmer ocean, greener desert, quieter vibes.

But I’ve picked up a few clauses:

No one is as obsessed with you as you are.

Naps will make you snappy.

Your body has an expiration date, but management refuses to disclose it.

Most things you worry about will never happen.

You will eventually become your parents in precisely the ways you swore you wouldn’t.

Objects in the rearview mirror may appear more meaningful than they actually were.

Past performance is no guarantee of future happiness.

And this one seems particularly important:

Terms and conditions are subject to change without notice.

So should we study the fine print?
Highlight it?
Memorize it?
Build our lives around avoiding
every known side effect?

Maybe not.
Because the fine print
is where the warnings live,

but the large print
is where life happens.
Fall in love.
Make the call.
Take the trip.
Start over.
Forgive sooner.
Dance badly.
Order dessert.
Laugh with Dad as he farts…again, when he stands up.

Yes, read enough of the fine print
to know that heartbreak, wrinkles,
loss, uncertainty, and death
are all included in the purchase price.

Then put down the contract.
Because perhaps the greatest danger
isn’t failing to heed life’s warnings.
It’s spending so much time
reading the fine print
that you forget
to live the headline.

In this episode of The Midlife Chrysalis, Chip Conley joins Derek Gehl to explore psychological richness and why curiosity, new experiences, challenge, and spontaneity become especially valuable as we age.

You’ll discover:

• Why psychological richness matters as we get older and how curiosity keeps us engaged with life.

• The question that can reshape your next decade: What will you regret not learning, doing, or investing in 10 years from now?

• Why becoming a beginner again matters, from learning a new skill to pursuing a passion you’ve neglected.

• Why spontaneity and stepping beyond routine enrich our lives and open us to experiences we might otherwise miss.

Watch the full episode and choose one thing you’re ready to finally do. 

Timestamps:

(00:02) Welcome to Wisdom Wednesday

(02:23) What Is a Psychologically Rich Life?

(05:58) Creating More Psychological Richness

(10:33) Reinventing Yourself in Midlife

(12:04) What Will You Regret in 10 Years?

(14:33) Is the Door Really Closed?

(16:04) Why We Regret What We Don’t Do

(17:48) Ways to Enrich Your Life

(20:24) Pilgrimages and New Experiences

(21:40) Curiosity and Leaving Your Comfort Zone

(22:08) The Power of Spontaneity

(24:01) This Week’s Challenge24:50 Make Your Commitment Public 

Learn more about MEA at ⁠https://www.meawisdom.com/

#PsychologicallyRichLife #PsychologicalRichness #ChipConley #MidlifeChrysalis #MidlifeReinvention #Curiosity #HealthyAging #LifelongLearning #GrowthMindset #MidlifePurpose #LifeAfter50 #LivingWithoutRegret #NewExperiences #MidlifeTransformation #Longevity

Our lives are overflowing with choices. But decisions are different.
Decisions are rarer. And they tend to have consequences.
The word itself offers a clue. Decision comes from the Latin decidere, meaning “to cut off.” When we truly decide, we aren’t simply selecting something. We’re cutting off other possibilities.

Think about some of the consequential decisions of your life.
I’m going to marry this person.
I’m leaving this job.
I’m moving across the country.
I’m starting this company.
I’m going to get sober.

These aren’t simply selections from a menu. They’re forks in the road. Once you start walking down one path, the others begin disappearing behind you.

And maybe that’s why decisions can be so terrifying.
We live in a culture that worships optionality. Keep your options open. Don’t close any doors. Maintain maximum flexibility. It’s understandable. An open door represents possibility.

But there’s a hidden cost to keeping every door open: you never fully walk through one.
At some point, possibility can become paralysis.

I wonder if we could think of our lives as having three levels:
Choice → Decision → Commitment
A choice expresses preference: This is what I want.
A decision establishes direction: This is where I’m going.
A commitment sustains that direction: I’m going to keep going even when another path starts looking attractive.

The distinction matters because we can spend enormous amounts of energy trying to optimize our choices when the more important question may be whether we’re willing to make a decision.

We ask, What’s the right choice?
Maybe a better question is:
What am I willing to decide?

There is rarely enough information to know whether a consequential decision will turn out to be the “right” one. Marriage, career changes, entrepreneurship, relocation, retirement—we make these decisions while peering through the fog of an unknowable future.

A decision isn’t certainty.
It’s commitment in the absence of certainty.
And there’s something liberating about that.

Perhaps the quality of our lives isn’t primarily determined by the thousands of choices we make each year. It’s shaped by the handful of decisions that redirect everything that follows.

Choices give us agency.
Decisions give us direction.
Commitments give our decisions staying power.

So, by all means, enjoy your choices.
Choose the entrée. Choose the shirt. Choose the movie.
But when you arrive at one of life’s great crossroads, remember that eventually you have to stop staring at the road signs.
You have to choose a road—and start walking.

I went on a road trip to southern New Mexico the weekend before this past one to experience two of the state’s enchanting natural wonders: White Sands and Carlsbad Caverns national parks. As you can see from the photos, White Sands looks like it’s full of snow and Carlsbad seems to be sprouting icicles, but it topped out at 105 degrees during my weekend journey, so there was no snow.

Did you know that 3 of the U.S.’s 27 UNESCO World Heritage Sites are in New Mexico (Chaco Canyon, Taos Pueblo, and Carlsbad) and White Sands is about to be added to the list, so this enchanted state will be tied with California for the most Sites of all 50 states?

Fall may be New Mexico at its most seductive. The summer heat softens into warm, crystalline days and cool, star-filled nights, while cottonwoods turn brilliant gold along the rivers and aspens light up the Sangre de Cristo Mountains. In Santa Fe, the chile harvest perfumes the air with the smell of roasting green chile, hiking becomes nearly perfect, and the high-desert light—the same luminous quality that has attracted artists for generations—seems even more dramatic against impossibly blue skies.

Add the Albuquerque International Balloon Fiesta in October, fewer summer crowds, harvest-season food and festivals, and the first dustings of snow on the mountains, and you get that rare combination of invigoration and coziness. Fall in New Mexico feels less like a season passing and more like an invitation to slow down and pay attention.

P.S. I’m so excited to be the first guest tonight in our Chrysalis House, a 5,000-square-foot home on 12.5 acres overlooking MEA’s Rising Circle Ranch campus created for four Golden Girls. You can read about all of our various housing options at MEA Homes. And we have a free online conversation with three MEA alums who tested out our Sage House in July and will talk about their experience of shared living tomorrow from 3-4 pm PT. You can sign up HERE. Lastly, AARP brought a journalist to one of our Golden Girls weekend workshops and the story was just published, Can You Live Like the Golden Girls? Our next Golden Girls weekend workshop (and the first one that is open for Golden Guys as well) is Nov 19-22 in Santa Fe.

In this episode, David Sinclair of the International Longevity Centre joins Chip Conley to explore what longer lives mean for all of us and why society needs to catch up with a future that’s already here.

In this conversation:

• Why the real longevity challenge isn’t living to 100, but adapting to longer lives today

• Why prevention needs to play a much bigger role in how we approach health and aging

• How longer lives are changing the way we think about work, money, retirement, and our communities

• Why purpose, connection, and staying engaged matter as much as staying healthy

• How the wisdom we accumulate over a lifetime can be shared with the next generation

Watch the full episode for a fresh perspective on longevity and what it will take to make our longer lives healthier, more purposeful, and more connected. 

Timestamps:

(03:13) Why Society Isn’t Ready for Longer Lives

(04:47) Why We Keep Ignoring the Aging Crisis

(07:13) What Governments Must Do About Longevity

(10:14) Why Prevention Should Come First

(12:01) Building Cities for Longer, Healthier Lives

(15:48) The Economics of an Aging Population

(18:09) Rethinking Life for the 100 Year Age

(20:39) Can Human Lifespan Keep Increasing?

(26:13) Living Longer Isn’t Enough

(27:18) Why Purpose Matters as We Age

(31:21) David Sinclair on the Other David Sinclair

(34:53) Who Is Getting Longevity Policy Right?

(37:53) The Responsibility to Pass on Wisdom

(41:04) The Business Opportunity of Longevity 

Learn more about MEA at ⁠https://www.meawisdom.com/

#DavidSinclair #InternationalLongevityCentre #Longevity #AgingSociety #HealthyAging #LongevityEconomy #AgingPopulation #FutureOfAging #PurposefulAging #100YearLife #LongevityPolicy #FutureOfRetirement #PreventiveHealth #AgeFriendlyCities #LifelongLearning

It’s getting hot down here in Baja as the humidity sets in for the season. Tropical air gets pushed up from southern storms, and our peninsula’s coastal desert turns into the tropics every summer.

Our office team at MEA is under a huge date palm in the courtyard outside the classroom while our workshop attendees are in session. We look up at the giant palm’s trunk on this very hot, stagnant afternoon. Everyone is at ease with the heat in this moment under the palm because we are focused on something different. We are drawing it. We’ve been doing this every afternoon for 15 minutes since mid-March. What started as a prompt from MEA’s co-founder, Jeff Hamaoui, to find a daily ritual at work to build connection among our team has officially stuck.

Every afternoon between 2 and 3 PM when a window presents itself, everyone who is working in our offices draws. Everyone takes turns choosing what to draw by bringing objects into the office on some days, and other days we go outside on campus. We all have the same tools: a sketchbook, a set of 4 pencils and an eraser. Some days it’s a flower cutting, others a cholla cactus stick. Water pitchers, fruit bowls, linen baskets, shells, you name it, and we likely have drawn it.

When we first started, the 15 minutes was a nice break from the afternoon. Four months later, the question of the day in the office has become, “What are we going to draw today?” but I’ve noticed a shift. Each day we go back to our desks, changed. I noticed it immediately, but it has taken me a few months to pinpoint exactly what was happening. Like stepping into the dark, you feel the change instantly, but your eyes take a few moments to bring everything back into focus.

Our everyday work sorts staff by competence, playing to each person’s strengths and placing them on an org chart whose hierarchy everyone in the room reads instantly.

Drawing, however, doesn’t see any of that. No one’s job title, experience in the industry, or management level makes them better at it. Everyone is equally vulnerable and has the same challenge of representing the complexities of an object in front of us with the same tools and limited time. No team-building exercise could quite accomplish this because the hierarchy, while politely set aside, still exists.

Alondra, our General Manager, shares the same difficulty as Luis, our purchaser, in representing the complex weave of a braided rope basket with just 15 minutes to do so. We all laugh at how our cholla cactus skeleton looks more like a French baguette than an artifact from our desert. Just yesterday I struggled my way through a session of red carnation flowers in a transparent glass vase. I had trouble with the reflections on the vase. The stems of the carnations were packed too tightly in the bottleneck, and my drawing got out of balance. Not enough volume in the foliage up top. Too dark in the neck, and the glass below was left feeling too light and unfinished. I looked over at Alondra when we finished and noticed she chose to eliminate the vase and just draw the flowers and leaves. Brilliant. Why didn’t I think of that?

We built this to be a low lift so we’d actually do it every day, but have stumbled on something more. 15 minutes in the afternoon is the keystone to why this works. We set timers for 5 minutes so everyone knows when they are a third of the way, and two thirds of the way through the exercise. That time crunch eliminates perfectionism. It forces instinctual mark-making. It’s just long enough to feel like a real event in the day, but short enough that it doesn’t eat into our day’s responsibilities and tasks. Everyone has 15 minutes they can spare, and many days it eclipses the other 7 hours and 45 minutes of work. It brings focus and clarity back to the afternoon. It’s a small window of time that has morphed how we relate to each other throughout the entire day.

Some days I cringe at my artwork. Other days I feel proud of my drawings. What always surprises me is how I never see the vulnerability in my coworkers’ drawings the way I do in my own, and how even on the days I dislike my drawings, someone else sees beauty in the way I solved the problem. I wish everyone could experience this because somewhere along the way, almost all of us have told ourselves that we are bad at drawing. None of us is good or bad at drawing; rather, drawing is an expression. It’s the information we see shared back on paper through our hands. Not a single one of us could draw like the other, even if we tried. It is fascinating how differently each of us takes in nuance and subtleties and distills complexity into simple marks. I have a new appreciation for our office team with a glimpse into how each of our brains processes what we see.

Today, someone placed 4 miniature cowrie shells collected from the beach out front on the corner of our desk. When I walked in the door this morning and looked at them and then looked up at Denise and Alondra, we all smiled at each other and without a word, knew what our next challenge would be.

Gail DiBerardinis is the Chief Operating Officer of MEA and is based in Baja California Sur. She has been with the organization since 2021 and especially loves leading teams on the ground in the daily rhythms of the campuses. The drawing ritual she writes about here began with a challenge from co-founder Jeff Hamaoui, and four months on, it has changed how the Baja office team moves through the workday.

Kai Soremekun is a writer, filmmaker, and believer in everyday magic. Drawing on four decades in youth-obsessed Hollywood, she created Joybellion, a philosophy rooted in the radical idea that joy is an act of rebellion in a culture that profits from women’s dissatisfaction. It invites women to reject the rules they’ve inherited and write new ones that feel true to them.

My book is here!

Joybellion: Transforming Midlife Insignificance into Freedom, Power and Everyday Magic

Join the Joybellion

It is the wrong question. Not because it is unimportant — because it cannot be answered from where most people are asking it.

I know this from my own body. I grew up in rural China during the Cultural Revolution. A fall when I was six left me with asthma that stayed for about thirty years. I was trained as a mathematician. I came to this work skeptical.

In 1997 I went back to China, to a center that people called the medicine-less hospital. The first trip was two weeks. Then a month. Then three months. Eventually I stayed two years.

Here is what people expect me to say next: that I found the practice that cured the asthma. That is not what happened. It is quite the opposite. What I learned there was to forget the diagnosis. Forget the expectation. I practiced for the enjoyment of my own body — enjoying the energy, enjoying myself, enjoying being alive. And that is where the change began.

The same reversal applies to your second act.

You are not short on clarity. Most people I meet in midlife have done that work. They know what matters. They know what they would love to build. What is missing is not the answer. It is the energy to live the answer — and energy does not come from deciding harder.

There is a particular tiredness that sleep does not touch. It is not a character problem and it is not simply age. Underneath it, almost always, is disconnection. The mind has been running the whole operation for decades while the body waited to be consulted. That disconnection produces the fatigue, the flatness, the strange absence of meaning in a life that looks full from the outside. I would call it the condition of our time.

The body is not a machine you are managing toward the finish. It is a living temple. And it responds — not to analysis, but to practice.

My logic is simple. If I can bend and move my spine today as much as I could yesterday, I can do this every day for the rest of my life. Thirty-five years in, I am still practicing. That is the whole point of my still being here.

In September I will spend three days at MEA’s Rising Circle Ranch teaching Wisdom Healing Qigong — movement, sound, and stillness that reconnect you to your own life force. You do not need experience. You do not need flexibility. You need a body and a willingness to feel it.

Come and find out what your second act feels like from the inside.

Master Mingtong Gu is founder of The Chi Center and author of Coming Home to Embodied Awakening. He teaches Qigong for Your Second Act: Real Energy for the Work That Matters at MEA’s Rising Circle Ranch in Santa Fe, September 3–6, 2026.

what is changing
to remain,

what is uncertain
to promise me
everything will be okay.

I suffer
because somewhere
I got the impression
the universe and I
had an agreement.

Apparently,
I did not read
the fine print.

The Buddha called it attachment.
I call it
my ongoing attempt
to negotiate with reality.

I grip the people I love.
The body I once had.
The future I imagined.
The identity that fit me
three versions ago.

And life,
with impeccable timing,
keeps opening my hand.

Not because love is wrong.
Because gripping
is not loving.

Perhaps freedom
isn’t letting go
of what matters.

It’s letting go
of my demand
that what matters
must last.

To love the flower
knowing it will wilt.

To love the sunset
without asking it
to stick around.

To love this life
without requiring
a lifetime guarantee.

Maybe enlightenment
isn’t floating serenely
above it all.

Maybe it’s simply
loosening my grip
one finger
at a time.

You forget why you walked into the kitchen. A familiar name takes an annoyingly long time to arrive. Your processing speed isn’t what it was at 25. And suddenly you start wondering whether your brain’s warranty has expired.

But a recent Washington Post article offers a refreshing reframe: some important aspects of our brains actually get better with age.

The article highlights three: fewer regrets, more knowledge, and more wisdom.

First, regret seems to lose some of its grip on us. Research cited in the article found that older adults reported fewer major recent regrets than younger adults. And when they did experience regret, they tended to feel less of the “hot” emotions like anger and frustration that accompany obsessing over what might have been.

Maybe we finally realize that the road not taken wasn’t necessarily paved with gold.

Second, while our fluid intelligence may decline, our crystallized intelligence can continue growing. Fluid intelligence is our ability to quickly solve novel problems. Crystallized intelligence is the accumulated knowledge, language, pattern recognition, and experience we’ve gathered over decades. Research cited by the Post found that adults in their 70s and 80s actually performed better on vocabulary tests than people in their 20s, 30s, and 40s.

I like to think of this as moving from a fast brain to a vast brain. That’s good, right!?

The younger brain may be quicker at finding the dots. The older brain has accumulated enough dots to recognize the constellation.

Finally, there’s wisdom.

Psychiatrist and wisdom researcher Dilip Jeste describes wisdom as including empathy, compassion, emotional regulation, self-reflection, and the ability to appreciate different perspectives. Research suggests several of these qualities can strengthen with age. During COVID, for example, older adults unexpectedly tended to fare better psychologically than younger people despite facing greater physical risk. One explanation? They’d lived through enough hard things to know that hard things eventually pass.

Maybe we need to reframe what cognitive aging means.
Yes, I occasionally forget a name.
But perhaps I’ve gotten better at remembering what matters.

Our culture tends to measure the aging brain by what it loses: speed, recall, processing power. What if we also measured what it gains?
Perspective. Pattern recognition. Emotional equilibrium. Empathy. Knowledge. Wisdom.

Perhaps the aging brain isn’t simply a younger brain that’s slowly breaking down.
It’s becoming a different kind of brain—less interested in speed and increasingly capable of seeing the big picture.
And maybe that’s not cognitive decline.
Maybe it’s cognitive evolution.

In this episode of Wisdom Wednesday, Chip Conley joins Derek Gehl to explore a new approach to later life: shared homes that combine independence, connection, and community.

Drawing on MEA’s growing Golden Girls experiment, Chip shares:

• Why traditional senior living and aging in place don’t work for everyone

• What MEA has learned from its first shared homes and Golden Girls retreats

• Why privacy, flexibility, and compromise are essential to making shared living work

• How shared homes can grow into vibrant “distributed villages” built around friendship, learning, and common interests

• How this model could inspire new approaches to housing and community far beyond MEA

Watch the full episode to discover a different way to think about home, community, and growing older.

Timestamps:

(00:00) Welcome to Wisdom Wednesday

(01:39) Rethinking How We Live as We Age

(05:05) The Golden Girls Shared Living Idea

(07:05) Sage House and Chrysalis House

(10:26) The Realities of Shared Living

(12:51) Are You Ready to Live With Others?

(14:46) Bringing the Concept to Other Communities

(16:38) Creating a Distributed Village

(19:09) The Long-Term Vision for MEA Homes

(22:09) What About the Golden Guys?

(23:05) How to Explore Golden Girls Living

Learn more about MEA at ⁠https://www.meawisdom.com/

#ChipConley #WisdomWednesday #ModernElderAcademy #MEA #GoldenGirlsLiving #SharedLiving #AgingWell #HealthyAging #PositiveAging #SeniorLiving #CommunityLiving #LifeAfter55 #Midlife #Longevity #AgingInPlace

“When in doubt, walk it out.” That’s been my 2026 theme. A good walk doesn’t just clear the mind, it nurtures the soul, especially if that walk is in nature, not on a treadmill.

On many levels, it’s been a tough year for me and there are many days when I feel no energy to walk due to being testosterone-free as part of my cancer treatment. But, the weekend before this last one, I endeavored to walk a marathon over a Saturday and Sunday. I didn’t quite make it, topping out at 23.5 miles and 43,000 steps over the two days, consistently walking on new trails over the Rising Circle Ranch’s four-square miles.

While some of the time, I was podcast-free, I spent much of the time listening to my friend Ivy Ross’ new podcast Phenomena about the growing scientific evidence proving the value of energy healing. I see the difference when I do a Qigong class with our neighbor Mingtong Gu (whose upcoming MEA Santa Fe workshop Sept 3-6 is called Qigong for Your Second Act: Real Energy for the Work That Matters) or visit Tibetan doctor Anne Millikin every other week in Santa Fe. I feel more vital even amidst the surgeries and rampant radiation my body has experienced, using the more traditional western approach to prostate cancer.

I was also doing this long walk to clarify my purpose and recommit to why I’m investing so much in MEA. I started the two-day walkathon with the question, “Nature, what can you teach me about how we should nurture and grow MEA at a time when I’m ailing?” Here’s the weird thing. When I got to the last 100 yards of my hike, as I was about to cross the arroyo right near my home, I saw something artificially colorful on the ground at the crossroads of the creekbed and the hiking trail (this is the primary place I usually start and end my hikes).

As I got closer, I noticed it was a celebratory, huge Happy Birthday balloon that, somehow, made its way to this particular place at this particular time on my two-day hike. Mark Twain said, “There are two most important days in one’s life: the day we were born and the day we figured out why.” Nature had given me a sign, a reminder about why I feel so purposeful in my stewardship of MEA. I’ve saved the balloon and will show it to you the next time you come over to my Wisdom Well ranch home for a pool party.

I will be leading a Marathon Walking Weekend Workshop May 6-9 next year. Imagine walking 26.2 miles over the course of a weekend, foot massage included! I hope you’ll join me.

The Happy Birthday balloon I discovered along with MEA guest faculty member Pico Iyer

Our attention splinters
into a thousand glowing pieces.

But perhaps the rarest gift
isn’t advice or answers,
but our undivided selves.

In a world of distractions,
be the presence others need.

Put down the phone.
Look into their eyes.
Listen beyond their words.

For someday we may discover
that the greatest present
we ever gave
was our presence.

In this episode of The Midlife Chrysalis, Chip Conley sits down with executive coach and Velocity Coaching founder Edward Sullivan to explore one of the most overlooked challenges of midlife: figuring out what comes after success.

Drawing on years of coaching founders, CEOs, and high achievers, Edward shares why so many people feel restless after reaching major goals, how AI is reshaping work and leadership, and what it really takes to build a meaningful life in the second half of adulthood.

Key insights include:

• Why success often creates unexpected emptiness

• How AI is changing leadership and work

• The role curiosity plays in personal growth

• Why self-care is a leadership skill

• A powerful question that can help shape your next decade

If you're navigating midlife, rethinking your priorities, or wondering what comes after achievement, this conversation offers practical wisdom for building a more meaningful future.

Watch now and discover what might be waiting on the other side of success.

Timestamps:

(01:14) Meet Edward Sullivan

(02:34) What Makes a Great Coach?

(04:54) AI Anxiety and Burnout

(06:44) Tuning the Instrument

(08:37) Coaching Young Founders

(09:42) Wisdom and Age Diversity

(12:49) Building Intergenerational Teams

(17:16) Curiosity Before Advice

(20:11) Midlife and the Happiness Curve

(22:37) Right-Sizing Expectations

(24:32) Why Success Can Feel Empty

(28:56) The Power of Small Experiments

(32:17) Designing a Meaningful Life

(35:43) Advice for New Coaches

(37:57) The Business of Coaching

(40:16) Finding Your Coaching Niche

(41:32) A Lesson Learned the Hard Way

(43:41) What Now Workshop

(44:18) Building a Career Crescendo

(45:38) Closing Thoughts

Learn more about MEA at ⁠https://www.meawisdom.com/

#LifeAfterSuccess #WhatNow #PurposeAndMeaning #ExecutiveCoaching #LeadershipDevelopment #CareerTransition #PersonalGrowth #MidlifeTransition #SuccessfulButUnfulfilled #SelfDiscovery #MeaningfulLife #ModernElder #ChipConley #EdwardSullivan #VelocityCoaching

When the moment arrived, she delivered it with total simplicity: We are all going to die. None of us are getting out alive.

It felt cheeky at the time, but it stayed with me. It also struck me how easy it is to live as if this isn’t true.

Today, after 30 years as a Risk Control Leader in global banking—and more recently, building frameworks for solo agers, caregivers, and families navigating life’s final chapters—that moment often comes back to me. If the finish line is non-negotiable, it raises a more useful question:

“What does a good death actually look like?”

To answer that, I’ve learned to reverse-engineer the exit.

In my former life, my job was to identify what could go wrong—and put simple, practical controls in place to prevent it. I still think that way today and I prefer things broken down to a “Schoolhouse Rock!” level of simplicity. When I strip this down to its essence, a good death comes down to four core domains—what I think of as the pillars of Aging Navigation:

The Body (Healthcare): A good death begins with awareness and acceptance. It means understanding when to shift from curing to caring—and choosing comfort, dignity, and quality of life over unnecessary intervention.

The Sanctuary (Housing): At the most basic level, we need to feel safe. A good death is grounded in a place that is clean, calm, and supportive—a space where the nervous system can settle, not brace.

The Order (Business Affairs): There is a quiet gift in leaving things in order. Clear documents, defined wishes, and trusted decision-makers reduce confusion and prevent unnecessary burden for the people we love.

The Soul (Purpose & Legacy): Perhaps most importantly, a good death is an anchored one. It means feeling connected—to people, to meaning, to the story of your life. It’s the sense that nothing essential has been left unsaid.

A good death isn’t luck—it’s alignment.

When our body, our environment, our affairs, and our sense of meaning are in order, we don’t just prepare for a peaceful exit. We create the conditions to live with greater presence and less fear right now.

So, as you look at your own life, which of these four domains is asking for your attention?

Because in the end, preparing for death is really about learning how to live.

“We’re all just walking each other home.” – Ram Dass

Patrick McCleary is the Founder and CEO of Act III – Aging Navigation, a platform dedicated to helping solo agers, caregivers, and families navigate the complexities of later life. After a 30-year career in global banking, he entered his own “midlife chrysalis,” setting him on a path of reinvention and purpose-driven work. That journey led him to completing End-of-Life Doula training at The University of Vermont and the Navigating Transitions workshop at MEA’s Baja campus, where he found a like-minded community and a new direction. An enthusiastic MEA alum, he is now a member of the inaugural MEA Purpose Fellowship.

But this is not a story about my divorce. This is about the unexpected arrival of poetry at a precarious time in my life, and the impact it’s had on my life since.

Although I was a writer, I hadn’t written a poem in 30 years. That I turned to poetry in the heat of that moment—not to a phone call, a walk, or another person—says many things about who I am and about the healing power of writing as a way through difficult times.

I had no idea, as I scrambled for a leaky old pen and started writing on an old napkin, that the poem I began writing in the car that day was one of many to come. That day marked a major turning point in my life, one that taught me how creativity could comfort and how writing poetry could help me better understand why my relationship failed, why I went on to date men who broke me, why my kids moving out left me so bereft.

For the first time in my life as a writer, I wasn’t writing for an audience. I was writing for myself, and that changed everything. For the first time, I wasn’t rushing something into publication. I was distilling momentous, emotional experiences into their barest essence, a very therapeutic practice. With these poems, I slowed down. I left them to sit and simmer, like a good stew. I went back over many years to add context, revelation, perspective. The flavors deepened.

The poems helped me turn my heavy emotions into something manageable, something I could learn from, something in my crumbling, unravelling world I could control. They helped me transform pain into something beautiful, and ultimately led me back to loving myself, a skill I had lost in a long, unhappy, unsatisfying marriage.

But the thing I loved most was how poetry prompted important questions that I had somehow failed to ask: Why did I put up with a man who made so little effort for so long? What was it about a chance meeting with a young boy in Burma that so affected me? What could I do with all my sorrow?

The process of asking and sitting with those questions didn’t always lead to answers, but it certainly helped me see with more clarity and understanding what had happened to me and why, and what I was going to do with this next season of my life.

That reinvention is what unfolds in my new book of poetry, a collection that explores my journey into this “fifth season.” That time in our lives as women where we are unnamed and unlabeled. No longer young, but not yet old. No longer maiden or mother, but not yet crone. A liminal time of uncertainty and questions and thresholds and rediscovery. A time for reinvention and rediscovery and reimagination.

The poem that started in my car on that miserable day now bears little resemblance to the poem that evolved over many years. What it became is a snapshot of a moment when everything changed. It contains all the fear and hope I felt in that moment, and it’s something I could never write today. I don’t feel the same; I’m no longer the same person.

But when I read it, I am transported back in time to the woman in the car who couldn’t see a way forward. And I am grateful to that heartbroken version of myself who took a pen and poured her heart out, word by ink-stained word, leading me to grow, learn and evolve into this new season.

Cori Howard is a Vancouver-based writer and author of the new poetry collection, The Fifth Season, which became available this month in the US. You can learn more and pre-order HERE

“They come to us, from shelters or friends or in any number of ways, these beings of fur or feather or other outer shells. They come to us wanting only to be fed, sheltered, and loved. And we take them into our homes and our hearts.

They may have prized pedigrees, or they may be abandoned or abused and rough around the edges. But there is something about them, some sort of light in their eyes that tells us they are meant for us. And a sweet dance of love begins with our new friends. We watch them delightedly discover their new home, laugh at the antics of kitten or puppy, smile as the former lost soul settles comfortably into our arms. They become a beloved member of our family, a reminder of the uninhibited joy that we have often forgotten how to feel.

The dog that excitedly runs to greet his human friend returning home, or the contented cat curled up on a lap remind us of how large unfettered love can be. They come to teach us to remember how to love. They come to teach us that our hearts, so often battered by this world that we struggle through, are still open enough to feel wonder and mystery and a precious connection to another being. And we love them, and care for them, and experience the joy we thought was lost from our lives.

But life is fragile. One day, perhaps unexpectedly, or perhaps after a long struggle with illness, our precious friends are gone. And we mourn them deeply. We feel lost, and alone, and that the joy is once again gone from our lives. We feel anger, and pain, and fear. We question Deity, and wonder why. Life is fragile. Their lives are more fragile than ours. We cannot escape death, and for it to take our most precious friends, who ask so little, seems unfair and too much for us to bear.

But they leave us always with a gift. They leave us with that love they gave, that joy they sparked. Our hearts are larger for having loved them. We are enriched by having these special souls in our lives, even if it was for too brief a time. Love never dies. And the love that was created by our special friends who came into our lives is a living thing, always a part of our being.

We may think our hearts are closing again, but we cannot erase the fact that they have been opened. They teach us love for a reason: so that we will have it in our hearts always. Each day, each act of kindness or love, is a tribute to our pets who have moved on. Honor your special friend with kindness and love.

Each day, reach out to your living companions and let them know how precious they are. Reach out to others in your life and let the love your friend brought you live on. Reach out to others in need, whether human or animal. I can think of no better gift than the love they teach us. And I can think of no better way to honor their memories than by extending that love. In this way, they will truly live forever.”

Arun Gupta, CEO of NobleReach and co-author of The Mission Generation, joins Chip Conley for a thoughtful conversation about finding purpose, staying curious, and creating a meaningful career at every stage of life.

Some of the ideas they explore:

• Why following your energy can lead you somewhere a career plan never could

• How becoming a beginner again can bring fresh energy to midlife

• Why learning, earning, and giving back can happen throughout our lives

• What younger generations can teach us about work and purpose

• Why our most human strengths matter even more in the age of AI

From leaving a 20-year career in venture capital to stepping into the vulnerability of teaching and public service, Arun shares why the next chapter doesn’t need to be mapped out before you begin it.

Watch the full episode of The Midlife Chrysalis.

Timestamps:

(03:39) Arun Gupta’s Mission-Driven Journey

(09:05) From India to Venture Capital

(12:50) Why Careers Don’t Follow a Straight Path

(16:28) What Gen Z Is Teaching Us

(20:33) Rethinking Learn, Earn, and Return

(22:33) Finding New Purpose Later in Life

(25:07) What Makes a Great Mentor

(29:24) Learning Across Generations

(33:23) AI and the Future of Work

(36:17) Building Human Capital in the AI Age

(39:25) Arun’s Midlife Career Reinvention

(43:46) What Problem Do You Care About?

(47:24) Doing Good and Doing Well

(49:00) Rebuilding Trust Through Interdependence

Learn more about MEA at ⁠https://www.meawisdom.com/

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