Introducing the Modern Elder Academy with Chip Conley

Morning, Greg here! Welcome to Issue No. 16 of Midlife Male, the lifestyle magazine for midlife men, by midlife men. I wanted to personally welcome all our new readers, and if this newsletter was forwarded to you, subscribe below.

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How I See It With Chip Conley: Founder of Modern Elder Academy

Chip Conley on the TED stage.

I have a confession to make: I often struggle with being open-minded and accepting of other people’s viewpoints. It’s a lifelong thing. I know I can be a stubborn guy, which is one of the reasons we named this series 'How I See It,' because I think it is so important to understand, embrace, and learn from how other men see things and the manners in which they have navigated and grown throughout their lives.

Chip Conley is one of those men. He's a guy who I normally wouldn't gravitate towards because it's harder for me to seek out the sensitive, the empathetic, the learners, the softer side of strength – the mental, emotional, and spiritual side of strength. These are the muscles that don't always get enough reps and are not often enough a priority for me.

I’m rarely in awe of another man’s physical strength. Sure, a big lift or feat is impressive, but I understand it. I know exactly what it takes to develop physical strength, to move heavy things. I understand that purpose, the process, and ultimately, the payoff.

But what I truly marvel at is men like Chip Conley—men who are very different from me, who have a different kind of strength, grit, and perseverance, and an incredible entrepreneurial spirit. Men who battle cancer and win. Men who create businesses of tremendous value. Men who lift others up and build real community, connection, and collaboration. Chip is one of those men.

The way Chip lives and what he represents is in many ways the opposite of how I was raised and what I’ve traditionally thought of as strength or masculinity. He’s the kind of guy who speaks openly about transformation, about becoming a “modern elder,” and even uses imagery like chrysalis and butterflies—stuff that I used to cringe at because it felt like the antithesis of traditional strength. But I have the utmost respect for men like him who so freely, securely, and beautifully spread messages of positivity and build magical places like Modern Elder Academy, impacting how thousands of people see, function, and thrive in middle age.

Getting to know Chip, having him on the podcast, and spending time at the Modern Elder Academy, was one of my favorite experiences—getting out of my comfort zone and coming out better on the other side. I believe the word they used to describe me at graduation was “softening”. Watching how Chip has developed himself as a modern elder, how he lives, leads, loves, and guides by example, has broadened my perspective on what true strength and growth can look like; which is the definition of maximizing middle age.

Chip’s journey is a testament to resilience, reinvention, and the strength found in vulnerability and community. For those of us navigating this stage of life, his perspective can be both challenging and deeply inspiring. This isn’t just about self-improvement; it’s about embracing a more connected, purpose-driven approach to aging that defies traditional boundaries of strength and success. Please enjoy this ‘How I See It’ interview. I think you’ll come away with a fresh sense of what’s possible for yourself, your relationships, and your future, just like I did.

– Greg

MLM: I first heard about the Modern Elder Academy through a post by Tim Parr from Caddis about his experience at one of your retreats in Baja. I looked into it and your incredible backstory, and I was blown away. This concept feels groundbreaking. What led you to create the Modern Elder Academy?

Chip Conley: It’s really a two-part story. I started a boutique hotel company, Joie de Vivre, at 26 and grew it into the second-largest boutique hotel company in the U.S., with 52 hotels in California. I loved it for 22 years, but by 47, I was burned out. The Great Recession hit, and during that time, I tragically lost five male friends in midlife to suicide. I hit my own dark night of the soul and even had a near-death experience (NDE) when I flatlined nine times due to complications from an allergic reaction.

I sold my company at the bottom of the market, and as I rebuilt my life, I began reflecting on how challenging midlife is for so many. Two years later, I joined Airbnb as their “modern elder.” At 52, I was twice the age of most employees. Initially, I resisted the title, but when they described a modern elder as someone “as curious as they are wise,” I embraced it.

While writing my book Wisdom at Work: The Making of a Modern Elder at my home in Baja, I had what I call a “Baja Aha.” I realized we lacked spaces where people could reimagine and repurpose themselves in midlife. I wished something like this had existed for my friends who took their lives—and for me during my low point. In 2018, we opened the Modern Elder Academy in Baja, and since then, it’s grown to include locations in New Mexico, a regenerative residential community, and online offerings.

MLM: When you decided to launch the Modern Elder Academy, did anyone question your decision?

Chip Conley: Oh, absolutely! I had people asking, “Chip, have you thought this through? Why invest in this?” My mother had similar questions. So, before officially launching, we ran 13 beta workshops in 2018, hosting about 160 people in Baja for free. The response was overwhelmingly positive. Participants felt a deep need to reframe their relationship with aging.

One key piece of research that reinforced this came from Dr. Becca Levy’s book Breaking the Age Code. She found that shifting from a negative to a positive view of aging can add 7.5 years to your life. It’s not just about living longer—it’s about thriving. Participants in our beta program even asked for an alumni network, which validated the program’s impact and led us to open to the public.

MLM: I love your approach to reframing aging. I’ve always rejected the term “anti-aging.” Aging is a privilege. How do you help people embrace this perspective?

Read the Full ‘How I See It’ Interview

Andrew Huberman and My Case Against Biohacking

Do less, better.

Science is boring. Call me a simpleton, but I don’t want to listen to three-and-a-half-hour podcasts and hour long speeches and deep dives into the minutiae of data, research, studies, hypotheses, counter studies and convoluted mixed messages of what we should and should not be doing all in the name of health & wellness.

I’m interested in health and wellness, not biohacking.

Big difference.

We’ve over-indexed and have men thinking that if they don’t do all of these things, take all of these things, hack every aspect of their health and spend countless hours, time, energy and money all in the name of longevity, then they’re not going to be “optimized”.

And it’s wrong.

I have other things in my life that are much bigger priorities—like my kids, my wife, my business, finances, friends, fun and my actual health and wellness.

When it comes to health, longevity, fitness, nutrition, recovery, and subscribing to all of the science, and listening to the Hubermans, Mark Hymans, David Perlmutter’s, and the rest – the vast majority of it is completely impractical, unrelatable, unattainable, unsustainable, undesirable and not even aspirational for me to try to live by.

I had dinner with Don Saladino on Friday night in Palm Beach just before the Eudemonia Summit began and we got to talking about the basics.

What actually really works in application.

What we’ve experienced in 30 years of trial and error. Testing and retesting. And quite frankly, we’re doing pretty fucking well for a couple of men in their late 40s and early 50s; who are husbands, fathers, run businesses, AND prioritize our health, fitness and overall wellness.

I was captivated by Timbaland’s story at Eudemonia; and his personal transformation to lose over 100lbs and get healthy. I enjoyed hearing exactly how he did it alongside his trainer Phil Daru and how it encompassed the simple, measurable, quantifiable basics along with discipline and consistency. No hacks, no shortcuts. And each time Dave Asprey kept trying to take him down some obscure rabbit hole he was just like “nah, man…”…

And that’s what I want to get at in this Viewpoint:

Read VIEWPOINT

Millions of stories are posted online every day and 99.9% are noise. We sifted through the nonsense to share standouts with actionable takeaways you can use to maximize your life in each of our 6Fs: Fitness. Family. Finance. Food. Fashion. Fun. Let’s go.

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FAMILY – The Value of 25 Minutes of Being a Beginner Together

FITNESS – Try this 30 & Up Fitness Challenge

FINANCE – How Bitcoin Hit $90,000

FASHION – The Super High ROI Face Tanner

FOOD – This Is What I Eat: Greg Scheinman’s Daily Food Diary

FUN – Listen to the Middle Aged Dad Jam Band with Ken Marino