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Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age

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New York Times bestselling author and co-founder/CEO of The Modern Elder Academy “reminds us all to savor the wisdom, self-knowledge, and joy that accompanies [the middle decades] of our lives” (Father Richard Rohr) and “provides a clear blueprint for creating the lives we want” (Gretchen Rubin)

The midlife crisis is the butt of so many jokes, but this long-derided life stage has an upside. What if we could reframe our thinking about the natural transition of midlife not as a crisis, but as a chrysalis—a time when something profound awakens in us, as we shed our skin, spread our wings, and pollinate our wisdom to the world?

In Learning to Love Midlife, Chip Conley offers an alternative narrative to the way we commonly think of our 40s, 50s and 60s. Drawing on the latest social science research, inspiring stories, and timeless wisdom, he reveals 12 reasons why life gets better with age. They
The relief of “my body doesn’t define ” We finally grow comfortable in our own skin Stepping off the We redefine what a successful life looks like The “Great Midlife ” We let go of our emotional baggage, mindsets, and obligations that no longer serve us Growing We begin to feel a part of something bigger than ourselves
No matter where you are in your midlife journey, this perspective‑shifting guide will inspire you to find joy, purpose and success in the years that lie ahead—and how those years can be your best ones yet.

Audible Audio

Published January 16, 2024

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About the author

Chip Conley

12 books153 followers
At the age of 26, Chip Conley started his own hospitality company, Joie de Vivre (JDV), and, as CEO for two-dozen years, expanded it into a collection of over 35 award-winning hotels, restaurants and spas – the second largest boutique hotel company in the U.S. The bestselling author of PEAK, Chip is a veteran practitioner of emotional intelligence in business and in his latest book, EMOTIONAL EQUATIONS, he takes us from emotional intelligence to emotional fluency. The preeminent thought leader at the intersection of psychology and business, Chip speaks around the world on finding meaning at work, is a regular blogger on The Huffington Post and his own blog at http://www.emotionalequations.com . Chip has been honored with the highest accolade in the American hospitality industry, the coveted ISHC Pioneer award, and was named the Most Innovative CEO – and JDV the "2nd Best Place to Work" – in the entire Bay Area by The San Francisco Business Times. He received his BA and MBA from Stanford University, and holds an Honorary Doctorate in Psychology from Saybrook Graduate School & Research Center, where he is the school’s 2012 Scholar-Practitioner in residence.

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5 stars
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453 (38%)
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378 (31%)
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Displaying 1 - 30 of 134 reviews
9 reviews1 follower
February 18, 2024
"Beware of inviting me to a cocktail party! I tend to ask inappropriate questions such as 'In what ways are you a beginner right now'?

If that type of conversation excites you, you'll likely adore this book from start to finish. If a complete stranger approached me that way, I'd think they were unhinged.

Conley isn't unhinged, and I loved the first half of the book, to the point where I was preparing to recommend it to several friends.

Unfortunately, the book turns into hot garbage in the back stretch. Conley pads it with anecdotes from his uber-wealthy friends, who have the means and time to travel the world for months, if not years, in search of themselves. As someone who isn't part of the 1%, I rolled my eyes at most of this stuff. The advice is utterly unusable for the vast majority of us, which Conley never acknowledges (Conley also touts his role in building the exploitative gig economy, which doesn't help.)

Conley also takes inspiration from horrific people, both real and fictional. He unironically celebrates Woody Allen's character in Manhattan (a man who has an affair with a teenage girl) and Kevin Spacey's character in American Beauty (a man who tries to have an affair with a teenage girl). He champions Joseph Campbell, to mixed effect, and tells a ton of dad jokes.

There's a lot to hate in Chapters 7-12, but the first 6 are full of sage advice, optimism, and joy. I wish I'd stopped there.
Profile Image for Jill.
674 reviews
March 15, 2024
Maybe life gets better with age if you have the financial resources to take a "gap year" and pursue your "passion project," or perhaps head to Mexico and figure yourself out at Conley's "Modern Elder Academy," which he touts several times throughout the book. But for the rest of us middle class schmucks trying to deal with the emotional and financial realities of the nascent empty nest years, there's not much help here.
Profile Image for Markie.
474 reviews34 followers
August 26, 2023
**Book Review: "Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age" by Chip Conley**

"Learning to Love Midlife" by Chip Conley presents a refreshing and empowering perspective on the often-misunderstood phase of midlife. As the co-founder and CEO of The Modern Elder Academy, Conley draws on his expertise to challenge the notion of midlife as a crisis and instead presents it as a transformative period filled with growth, wisdom, and new possibilities.

In this book, Conley offers readers an alternative narrative to the conventional view of midlife. He invites us to reframe this stage of life as a chrysalis—a time of profound awakening and transformation. Through a combination of the latest social science research, compelling stories, and timeless wisdom, Conley presents 12 compelling reasons why life improves with age.

One of the key themes explored in the book is the concept of shedding societal expectations and embracing self-discovery. Conley highlights the relief that comes with realizing that "my body doesn't define me," allowing individuals to grow comfortable in their own skin. He emphasizes the importance of stepping off the treadmill of external pressures and redefining success according to personal values and aspirations. The concept of the "Great Midlife Edit" underscores the idea of letting go of emotional baggage, limiting mindsets, and obligations that no longer align with our evolving selves.

As readers delve into the book, they'll find inspiration in Conley's exploration of how midlife offers opportunities for growth and connection. The concept of "growing whole" resonates as individuals begin to feel a sense of belonging to something greater than themselves, leading to a deeper understanding of purpose and fulfillment.

The writing style is engaging and accessible, making complex ideas relatable and actionable. Conley's storytelling is a blend of personal anecdotes, scientific research, and philosophical reflections, creating a narrative that is both insightful and motivational. He draws from a variety of sources to illustrate his points, ensuring that readers from all walks of life can find resonance in his words.

"Learning to Love Midlife" is not only a guide to navigating the middle decades of life; it's an invitation to embrace the richness and potential that come with age. Chip Conley's book offers a roadmap for finding joy, purpose, and success during this transformative stage. Whether you're already well into your midlife journey or approaching it with uncertainty, this book provides a perspective shift that encourages readers to view midlife as a time of renewal, growth, and self-empowerment.

In conclusion, "Learning to Love Midlife" is an illuminating and empowering read that challenges societal norms and embraces the beauty of aging. Chip Conley's insights and wisdom serve as a guiding light for those seeking to make the most of their middle years and beyond. This book offers a fresh perspective that celebrates the growth, wisdom, and potential for transformation that come with the passage of time.
Profile Image for Shana Kennedy.
386 reviews17 followers
February 29, 2024
Well-intentioned, but just an endless series of cheesy cliches and plays-on-words.
Profile Image for Alla.
34 reviews5 followers
March 15, 2024
Trite, vapid, and super niche (written for wealthy white dudes in midlife). This author simultaneously advocates stepping off the hedonic treadmill and rapturously recounts his instagram reel of traveling to Pamplona, Bali, Maha Kumbh Mela, among other “eat, pray, love” type of destinations. Unironically gushes over The Burning Man. 😂

One additional star for an occasional accidental good quote, as well as for the author’s own very briefly shown vulnerability in describing his darkest moment.

Profile Image for debbicat *made of stardust*.
855 reviews125 followers
July 2, 2025
4 stars! I enjoyed this! I saw the author on a daytime talk show and was intrigued. Lots of wisdom here about middle age and the second half of life. Didn't know the connection with Richard Rohr when I requested this to read. I am a huge fan of Rohr. Lots of great information here for those in their 40s-60s. Embrace all of the changes. Slow down and really live. It is a great part of life to be in. Aging comes for everyone. Lots of positivity and hope.

Many thanks to NetGalley and the publisher for a digital copy to read for review. I highly recommend it!
Profile Image for Elizabeth.
2,321 reviews56 followers
March 27, 2024
I liked Chapter 10 which speaks to having time to be a beginner again. I love this thought. I can try new things but I can also pick back up things I tried once upon a time but veered away from. Life is amazing. Questions for defining your legacy (p. 173) were terrific for narrowing down on mission. Each life stage has its upsides and downsides!
Profile Image for Kayti.
365 reviews1 follower
August 1, 2025
Audiobook. Meh. There were a few good nuggets but a lot of cliches and things that didn’t line up with my faith practice. While I don’t mind reading authors who don’t share my beliefs, this topic really needs more alignment in my opinion.
269 reviews58 followers
November 1, 2025
I felt this book had a good premise, but it fell down in execution. The chapters had a decent length but they didn't seem to say much. I was looking for solid information and in the end I felt like I read nothing helpful.
241 reviews
February 18, 2024
Nothing groundbreaking, but a good motivational that people are happier the older they get.

Recommended reading for mid-lifers. Not worthy it a second read.
53 reviews1 follower
April 16, 2024
I read this having had it recommended by someone I have a lot of time for, but it wasn’t really for me: I am far too much of a sceptic. And yet, and yet…. Some pages and passages were really thought provoking.
396 reviews15 followers
January 10, 2024
This book hits home as a woman who would be considered midlife. I thought this approached the topic in a way that didn't feel preachy or like it was trying to solve every problem. It was honest and refreshing.

Thanks to the publisher and NetGalley for advanced copy, and I give my review freely
Profile Image for Lani.
585 reviews
March 8, 2024
I listened to this on audio and the amount of audio changes which I assume are from editing are terrible. Many times the volume or pace of speaking changes mid chapter. It's very distracting.
That being said, the content wasn't all that interesting or life changing either. Not impressed.
Profile Image for Salena Copeland.
74 reviews1 follower
May 21, 2024
This book seems targeted for a very specific audience. Not just those in or approaching mid-life, but also those who can afford to take a “gap year” of not working in their 40s or 50s without worry about their bills and financial obligations to family, not fear of finding work when they decide their gap year is over. That said, I did find some of the ideas match what I’ve been struggling with - how to find time to be a lifelong learner, how to try being new/bad at something, and how to build in time for rest and connection now, in my 40s, rather than busting my ass until I’m 65 and THEN I get to rest. Maybe the trade off is working for pay for longer but enjoying life now a bit more.
Profile Image for Elizabeth .
84 reviews1 follower
Read
September 3, 2024
Passages I liked:

“If you yield to the chrysalis call [rather than thinking midlife is a time of crisis], it means that the incessant accumulating (the caterpillar consuming) must come to an end. This means dropping mindsets, habits, identities, stories, and choices made when we were younger, which no longer reflect who we are or who we're meant to be. As David Bowie is reported to have said before he passed away, way too young, ‘Aging is an extraordinary process whereby you become the person you always should have been’” (7–8).

“How are you preparing for the second half of your adult life? If the first half was learning the rules, could the second half be about breaking them? And one of the key rules to break is the societal mindset that midlife is boring and uninspired. Break convention. Break habits. Break free!” (37)

“For many, midlife is when we start to treasure our relationships more than our possessions. And, as Dutch sociologist Gerald Mollenhorst has shown, we replace half of our social network every seven years or so, so investing in friendships is a lifelong endeavor. If you don’t invest, your network will atrophy” (73).

“In a world that is changing faster than ever before, the ability to master transitions has become an essential twenty-first-century skill. So don’t let the prospect of unfamiliar soil scare you from exploring what’s next. You might be able to plant your seed in many places by thinking of your work life as a portfolio of activities” (155).

“With age comes alchemy. Maybe your mastery is the combination of two of your identities or skills. ... Finding two skills that you can alchemize is a way to find your unique gift” (161).

“The goal of becoming a beginner in midlife is not just to get smarter or more proficient at something: it’s to approach life with fresh eyes. Becoming a beginner allows us to reengage with and rediscover natural talents we can build at any age. Taking this leap gives us confidence at the exact time we need it most. It turns back the clock” (170).

Profile Image for Chris.
474 reviews4 followers
May 24, 2025
Well like many of these books it’s got the brag feeling of “when I took a gap year in mid life and went to a gazillion conferences” and blah blah blah. Sure buddy. Do that. No one else does that.

The acclaim for his program and center hidden by some story of someone who was transformed at your retreat—yeah just advertising your own stuff.

When “I started at Airbnb or VRBO (whatever one it was) and I made more millions”…yeah whatever we get it money doesn’t make people happy. We all see the misery of most rich people daily.

When I was chosen to help the pastor of some mega church do the offering I was amazed and in awe of my awesomeness. Seriously? Just stop.

Did I like any of this book? Meh. A few things here and there. Basically, live in the moment. Live purposefully. Live bravely. Live fully. Getting old and getting wise are better than dying young.

Does this author have any expertise? No
Does this author write well? No
Does this author narrate well? Yes
Does this book transform anything in my life? No
Do I wish I read it? No
Profile Image for Mai Nguyen thuy.
59 reviews1 follower
December 7, 2024
At 35 which is probably midlife of the health span (rather than lifespan) I thought it’s an interesting read to get a glimpse of what’s ahead.
Despite the bad reputation midlife has, the author argues that this could be the transformational Chrysalis period that let you bloom into a butterfly 😂
I tend to agree - It’s true that in my 20s I looked at others, followed a safe path and didn’t know what I truly want. I feel much more in control of my life now, as I’m fortunate to have the stability and means to purposefully start crafting a life that I’m looking forward to.
Some reasons why life gets better with age:
- The great edit: letting go of mindsets and obligations that no longer serves you
- “Stepping off the treadmill”: define what’s a successful life to YOU that could mean finding new use for your expertise, exploring career and hobby options, investing in relationships and communal joy
- “Be a beginner at something”: never stop learning and get new experiences

There are some cliché bits trying hard to bleech white middle-aged men stereotypes but hey, after all, aging is a privilege, a gift of time that our ancestors didn’t have.
Profile Image for Sbwisni.
376 reviews2 followers
December 22, 2024
4.5 About half the chapters had reflective or profound things for me and where I am in life (as a full-time working 42 year old mom with aging parents), but enjoyed listening to most. Will come back and add bookmarked quotes later!

Listened on audiobook.
Profile Image for Will Peterson.
44 reviews5 followers
April 17, 2024
Meh. Occasional insights, but too much pithy nonsense and T-shirt slogans. Abandoned halfway.
Profile Image for Dianna.
234 reviews
July 3, 2024
2.5 The first half was pretty insightful but the last 4 or 5 chapters felt like a different take on the same ideas. Could've easily been 6 reasons explained with less filler
183 reviews
July 4, 2025
Audiobook - had some good exercises/questions to get you thinking.
Profile Image for Charmin.
1,077 reviews140 followers
June 2, 2024
HIGHLIGHTS:
1. Middle age is knowing what YOU want from life.

2. KNOWING what you want from life allows you to CONTRIBUTE to life.

3. ACTION:
- Write out your 10 commitments of how you were going to live your life.

4. INVISIBLE:
- We all want to be seen and appreciated for who we are.

5. WISDOM COLLECTION:
- Harvest daily wisdom in a journal.

6. DIVULGE WISDOM:
- Make a list.
- Make a highlight list of things that you learn this year. Share

7. SERENITY PRAYER:
- Recite the serenity prayer everyday.
- Identify what you have control of and what you do NOT have control of.

8. METABOLIZED EXPERIENCE:
- Regularly ask yourself what you learned.

9. WHOLENESS:
- Wisdom isn’t taught, it is shared.
- We are meant to be whole.
- Life gets more interesting when there is a limited amount of time left.

10. REGENERATION:
- When does “growing” stop and “aging” begins?
- old and growth can be synonymous
Profile Image for Mia Henry.
108 reviews1 follower
June 20, 2024
More like a 2.5 for me. Maybe a three for someone new to these types of books. I heard very little new information. He is just telling his own discovery stories, telling the stories of others, or quoting people who are more profound. Honestly 80% of this book is the author sharing the wisdom of others but I’ll bet they are not getting any proceeds from sales! At the end he asks people to send him their stories. Don’t do it, people!

This is also an extended plug for the author’s current venture - MEA - coaching people looking for meaning in midlife - which according to him is basically all of life after 25.

Warning I’m going to start getting petty now…

The author is super wealthy and swimming around in a world of other rich people looking for meaning after being some of the few who reaped the fruits of capitalism.

I listened to the audiobook and he laughs in it a little too much for me. It does not feel authentic. He also said a few things that rubbed me the wrong way. It seemed that he kind of made fun of or held in weird reverence things he doesn’t understand. It also reeks of false humility.

All this said. it was easy to listen to in the car and while cleaning. And now I say ROI means “ripples of influence.” I liked that reframing a lot.
Profile Image for Leslie Riley.
44 reviews1 follower
February 22, 2024
I needed & appreciated the perspective in this book after a particularly rough year that left me asking, “Is this all there is?!” As I stare 50 in the face, it has given me inspiration to embrace my next chapter in life with vigor instead of dismay. Except the chin hairs…not sure I will ever embrace those suckers.
Profile Image for Thea Marlowe.
559 reviews4 followers
March 14, 2024
Loved these quotes, says it all❣️

- Aging is a privilege, a gift of time.
- Growing and aging are the same thing.
- Happiness is not the same thing as joy; as author J. D. Salinger—who lived to 91—has written that “happiness is a solid and joy a liquid.” Happiness is often based upon external circumstances, but joy bubbles up from inside you.
Profile Image for Keilee.
16 reviews2 followers
August 13, 2024
Really enjoyed this read, even if I'm not technically in Midlife. However, I think those having any sort of crisis (quarter-life or mid-life) can learn from this book. Thematically, I really enjoyed the structure and focus of the chapters. A fun read.
Profile Image for Terri Mead.
Author 3 books13 followers
September 4, 2025
What Chip Conley Gets Right (and Wrong) About Midlife: A Critical Review
Learning to Love Midlife by Chip Conley | Read: July 2025

When several students in my Stanford Continuing Studies course “Navigating Midlife for Women” mentioned the Modern Elder Academy, I knew I needed to read Chip Conley’s Learning to Love Midlife. As someone who wrote Piloting Your Life specifically for women over 40, interviewing only women and focusing my research entirely on women’s midlife experience, I was curious about how Conley’s perspective would land.

Here’s the thing: Conley is more aware than most men authors writing about aging, and there are valuable insights in this book. But reading it reinforced exactly why I felt compelled to write a book specifically for women. Despite good intentions, Learning to Love Midlife falls into the familiar trap of treating the men experience as the default, with women’s experiences sprinkled in as variations on the theme.

As a 60+ gay man, Conley brings unique perspectives to aging, but many of his stories and examples, drawn largely from his own life and men friends, simply don’t translate to what women face in midlife. The book takes broad strokes at universal truths while glossing over the specific realities women navigate: workplace ageism that hits us differently, the particular challenges of menopause, the way society renders us invisible in ways that don’t parallel men’s experience.

That said, there are insights worth extracting. Here’s what I found useful in Conley’s research, viewed through the lens of what actually serves women in midlife.

TLDR: These takeaways focus on the research-backed insights that do apply to women’s midlife experience, while acknowledging where Conley’s perspective falls short. As always, bolded quotes come directly from the book.

https://medium.com/terri-hanson-mead/...
134 reviews
September 7, 2025
I've been embracing life in my fifties as, for the first time in my life, I have been able to overcome mental health challenges and simply appreciate life. In many ways, I feel like my life is just beginning.

As such, I wasn't looking for anything like this to read, stumbling across it while reading something else. Conley's book Peak helped form my attitudes towards leadership and business management and in some ways contributed to my making a shift, in what I probably called midlife in my thirties, from a career in statistics to becoming a librarian. Since then I hadn't heard or thought much about Conley and so the sudden appearance of this book on my radar prompted me to read it.

It turns out Conley dealt with mental health concerns soon after Peak was published and also emerged from them in recent years and he, too, is finding enjoyment in his life.

From my own experiences, I wonder how much of his appreciation of "old age" is simply being able to appreciate life in general but just happening to be older. It's hard to say because unlike Peak, whose precepts were driven by the work of Abraham Maslow, this book is more haphazard and based on Conley's personal experiences which, as many other Goodreads reviewers have pointed out, are greatly influenced by Conley having considerable wealth and connections at his disposal.

I still found the book educational, although probably not enlightening, and he cites a number of other books he has read which seem to have potential of providing a higher level of useful information than this book does. It's also a pretty quick read so I would probably recommend it to someone as a primer if they were struggling with what to do with their lives as they hit their 30s, 40s, 50s, 60s or whenever they felt an age-related shift occur.
Displaying 1 - 30 of 134 reviews

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