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Lessons from the Modern Elder Academy

Lessons from the Modern Elder Academy

Last updated on: October 29, 2025 at 3:49 pm by Carl Gregg

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Lessons from the Modern Elder Academy 2025-10-29T15:49:25-04:00 Carl Gregg

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In July, I had the opportunity to spend a week in Santa Fe, New Mexico, at the Modern Elder Academy, the world’s first “midlife wisdom school” (Learning to Love Midlife, 225). It was a stunningly beautiful place to be.

On the final day of the retreat, we embarked on a hike. The hill did not look like much, but keep in mind we were at about 7,000 feet above sea level. Here in Frederick, we’re at roughly 300 feet. I’m a runner, in pretty good shape, but by about halfway up that hill, I was breathing hard! It was worth it — the panoramic view at the top was spectacular.

I’ve come to think of that hike as a metaphor for the shift in perspective at the heart of the Modern Elder Academy’s midlife wisdom curriculum. Our culture has a persistent myth that once you turn 40, you’re “over the hill” — as if life’s best days are behind you and it’s all downhill from there. But from the perspective of midlife wisdom, we can reframe that story: we’re not over the hill — we’re on the hill. And from that higher vantage point, we have access to a more panoramic view of life — a perspective only possible through years of lived experience.

On the way back from that hike, I noticed a cactus growing from the space between two branches, about halfway up the tree. That cactus — growing in such an unlikely place — became another powerful metaphor for me of midlife wisdom. Sometimes experience shows us that growth and new life are possible in ways and places we never imagined possible. And even as some things fade, the sunset season of our lives can reveal a beauty beyond words.

We live in a culture obsessed with youth — afraid of aging, and in deep need of wisdom. And at the core of the Modern Elder Academy is the conviction that aging is not a sentence to become elderly — it’s an invitation to become an elder.

If you get the chance to attend a Modern Elder Academy retreat, I recommend it. You can go either to their Santa Fe campus or to their original beachfront campus on the Baja Peninsula in Mexico. I haven’t been there, but I’d like to go! If such a pilgrimage isn’t in the cards right now, the founder has written several books that share its teachings widely.

A great starting point is A Year of Wisdom with Chip Conley, a collection of daily meditations — each a page or less. He has also written Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, a book full of practical insights. And there’s Wisdom at Work: The Making of a Modern Elder, where he shares what it means to bring the gifts of experience into a new generation’s world — balancing the roles of mentor and learner.

For podcast fans, this summer Chip launched The Midlife Chrysalis, which has started strong. Early episodes feature conversations with Maria Shriver, Seth Godin, Marian Goodell (CEO of Burning Man), Krista Tippett, Elizabeth Gilbert, Anne Lamott, and more.

As we prepare to go deeper, it may help to take a moment to clarify what we mean by midlife. As people live longer, the definition is expanding — some sociologists now see it as stretching from about age 35 all the way to 75 (6).

Midlife is often associated with the so-called “midlife crisis,” the dip in life satisfaction many people feel in their forties (19). It’s the period when adulthood often confronts us with the gap between our youthful expectations and the realities of our lives (132). We may find ourselves wondering, “How did I end up like this?” (25). But if you’re in your forties and may live into your eighties, consider that you’re only at halftime in the game of life. “Your story is only half told” (25).

Research shows that “younger people tend to overestimate how satisfied they’ll be in five years, while older adults tend to underestimate future satisfaction” (132). And most people report feeling “better and happier in their fifties, sixties, and seventies,” and beyond (19).

The invitation of the Modern Elder Academy is to redefine the “midlife crisis” as a “midlife chrysalis” — the transformative stage in which the caterpillar prepares to be reborn (Love 36). Instead of a “crisis,” midlife can be better viewed as a “crossroads,” an opportunity for a “mid-course correction” — an invitation for a new story to emerge on the other side of the messy middle (203; Year 3/13).

There are some important reasons why life tends to get better and happier in our fifties and beyond. As we get older, it becomes easier to care less about what others think and instead to listen more deeply to our own inner voice (ibid 9/27). That shift — tuning in to what we most deeply value and most passionately care about — can be the catalyst that helps us thrive in the second half of life.

To quote an Internet meme, “We should start referring to ‘age’ as ‘levels’ because ‘I’m at level 68’ sounds more badass than just being an old person.” Or, more poetically, the writer Anaïs Nin put it this way: “The day came when the risk to remain tight in the bud became more painful than the risk it took to bloom” (Love 67). Have you ever felt like that? It can also feel like reaching the point where you just don’t have any more bleeps left to give. However we get there, reaching that threshold can give us permission to live differently.

I should hasten to add an important caveat from Mark Manson’s bestselling book The Subtle Art of Not Giving a [F**k]: “Not giving a f**k isn’t about being indifferent. It’s about feeling comfortable with being different” (86). And giving ourselves full permission to be different — to be fully and authentically ourselves — can make all the difference in the world.

What does that mean, specifically? Busting out of your midlife chrysalis can look like finally doing that thing you know you need to do. Inside, it can feel like saying, “Screw it — I don’t care how old I am — I’m going to…”

learn to play the piano.
take that trip I’ve always dreamed about.
clear out the clutter and make space for what matters.
volunteer for something that makes a real difference.
go back to school.
stop apologizing for who I am.
say “no” when I need to, without guilt.
forgive myself for what I can’t change. (Year 1/16).

I can’t tell you what that specific thing or things are for you. You have to look within and ask yourself, what would give my life more purpose and meaning — and then give yourself permission to go do it. I can tell you this: it boils down to the old adage: “Be yourself. Everyone else is taken” (ibid 12/31).

In developmental psychology, there’s a saying that adolescence is often deeply shaped by the dynamic of “When I see you seeing me, I construct the me I think you see” (James Fowler). When we’re in our teen age and early adult years, many of us are strongly influenced not by who we actually are, or even by who others truly think we are, but by who we think our peers think we are. Some people stay caught in this stage for their whole lives — forever chasing the approval of others instead of trusting their own inherent worth.

But the invitation of midlife is to get honest about who we actually are. Who am I, really? What do I feel most deeply called to do? This shift toward being more authentic and inner-directed reminds us why it’s vital to let go of seeing midlife as “over the hill,” and instead to embrace the wider view that opens up when we’re “on the hill,” rooted in the wisdom of our lived experience.

In contrast, consider my two-year-old: a single year represents half of his life. If he does or doesn’t get a cookie — or if he does or doesn’t get to keep playing with a toy — it can feel to him like a world-historic crisis. Perspectives change with time.

Or, when I was a youth minister, if we made a change in the program, it sometimes felt to the youth that we’d changed something that had always been that way — whereas we knew as adults that it had merely been that way for as long as that particular person had been in the youth group. Consider that “a year represents 10 percent of a 10-year-old’s life, but just 2 percent of a 50-year-old’s life” (Love 164).

That’s an “on the hill” perspective. You can start to ask yourself: Is this thing that feels so impactful in this moment really going to matter in five minutes, five hours, five days, five weeks, or five years? Brené Brown calls these the “Five Fs” (Atlas of the Heart 105). Thinking through these increments of time helps me take a step back — to discern between what will still have reverberations months or years from now, and what will likely fizzle within minutes, hours, or days. Can you feel the shift that perspective can bring?

It’s not that you can’t have longterm perspective when you’re younger. It’s just that when you’re older — a little more on the hill of life — perspective becomes more at hand, more second nature. Your views on life are less theoretical and more grounded in your many years of experience.

And that brings us full circle to why the Modern Elder Academy is known as a “midlife wisdom school.” The founder, Chip Conley, defines wisdom as “metabolized experience that leads to distilled compassion” (101). Wisdom emerges from hard-won experience — the kind you’ve had enough time and distance to process — so that you can be more compassionate toward others and toward yourself.

There’s an old saying about sermons: you should “preach from your scars, not from your wounds.” If I preach from my wounds, I’m going to bleed all over you, metaphorically speaking. It’s going to feel raw and unprocessed — more about my pain than about your growth or our growth. But if I preach from my scars, then I’ve already done some healing, and gained perspective on what I’m sharing — and it’s much more likely to come from a place of wisdom — “metabolized experience that leads to distilled compassion” (101). The same principle holds beyond the pulpit: wisdom comes when we’ve had enough distance to metabolize our experience — so our words and choices carry compassion and perspective instead of reactivity.

In the first half of life, our focus is often quite naturally upon learning, growing, and accumulating, seeking more knowledge, experiences, and possessions. Some common and age-appropriate mindsets focus on:

Achievement: “I am what I do.”
Image: “I am what others say about me.”
Status: “I am what I have.”
Power: “I am what I control.” (Love 146)

And some folks stay in that mindset for the rest of their lives.

But in the second half of life, the invitation of the midlife chrysalis is to shift your focus toward the deep inner wisdom of what truly matters. Once we’re far enough up the hill, we have enough perspective and experience to more clearly and skillfully discern how we do — and don’t — feel called to spend our finite time. Greg McKeown says it this way in his book Essentialism: “If it isn’t a clear yes, then it’s a clear no.” In midlife, we have gained enough clarity to realize, in the words of James Clear: “No is a decision. Yes is a responsibility.”

There’s a related adage that you should “say yes to everything before you’re 40…and say no to everything after you’re 40” (Love 168). That’s an exaggeration, but the underlying point is that in the first half of life, your default should be saying “yes” when you can. You need new experiences to learn which people, places, and activities give you energy, meaning, and purpose, and which ones leave you feeling drained and worn out. You need to know this — it not theoretically, through lived experience.

I promise you this: there are a lot of surprises along the way. There are so many people, places, and activities I thought I’d enjoy — or that others told me I would — that simply didn’t pan out in real life. And vice versa — so many people, places, and activities that I love that I never expected, stumbled backward into, or that turned out to be so different from what people told me. Anyone else experienced that?

I’ve been singing the praises of midlife, so let me also be honest that there is a partial truth behind the stereotype that anyone over forty is “over the hill” and on an inevitable decline: psychologists tell us that fluid intelligence — “our ability to process new information, learn, and solve problems — peaks in our early twenties.”

But the other half of the truth rarely gets told: crystallized intelligence — our brain’s ability to think holistically — actually improves with age and doesn’t peak until after seventy” (98). On the hill of life, we gain an increased capacity to synthesize — to access the wisdom that can only come from the perspective and experience that accompany age.

I began this sermon with a hike we took on the final day of the Modern Elder Academy retreat, so I will move toward my conclusion with a ritual that we did at the end of the first full day. If it resonates with you, consider doing this ritual later today or sometime this week:

Start by thinking about where you feel stuck in life, especially if it relates to an expectation you have about yourself. What keeps you up at night? Where do you feel like you’ve failed? What’s a belief you have that’s robbing you from living up to your full potential and feeling joy? What’s a habit or habitat you’re ready to junk? What’s a way of being or thinking that used to work, but doesn’t anymore?

Take a small piece of paper and write down all the mindsets, habits, and relationships you’re ready to let go. Read the list of things you’re editing from your life out loud, then light the paper on fire and throw it safely into a bowl or a fireplace. Watch it burn to a crisp. What are you ready to let go of in pursuit of a better second half of life?

Then, take out another piece of paper and list the mindset, habits, or relationships you’ll be adding to your life to replace what you’ve just edited.

If you wrote, “I’m terrible at yoga” as a mindset you want to edit, the replacement mindset might be “I love how I feel at the end of a yoga class.” [Give yourself permission to be the yogi that you are, not the yogi you or others think you should be. As the saying goes, “Stop should-ing on yourself.]
Or if you wrote, “I will never be as successful as I used to be in my career,” you might replace that with “I will define a new way to measure success in my career.”

You might shift “I’m too old to start over” to “It’s never too late to begin again.” Or reframe “I have to keep everyone happy” to “I can love people without losing myself. I matter too.” Or, “I’m bad at saying no,” to “Every no makes space for a truer yes.”

Don’t rush it. You may need some time and space for the deeper wisdom to emerge. Try taking this question on a walk and see what insights unexpectedly come to mind. Once you have shifted your mindset, write it down. “Don’t burn this piece of paper. Save it and savor it.” Maybe tape it up where you can see it regularly. “It is a guide for your future.” (140).

What new way of being in the world are you ready to embrace because you know deep down in your inner wisdom that it is a full-hearted yes?

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