The midlife renaissance
Crunching joints.
Demands from both children and parents.
Needing to make a noise to get up off the sofa.
Midlife can feel exhausting.
But what if midlife could be a chrysalis, not a crisis?
A transformative period of growth, self-discovery, and reinvention?
Joining us to explore this idea was Chip Conley, founder of the Modern Elder Academy and best-selling author of one of the best books for midlife, Learning to Love Midlife: How to Embrace What’s Next.
Chip offers profound insights from his work and personal journey, showing how midlife is not a crisis but an opportunity to curate the rest of your life with more intention, joy, and freedom.
This one’s for you if…
You want an inspiring new way to look at midlife and how to make the most of it
You want an intentional practice to draw wisdom from your experiences
You want to find your purpose, and need a different way to think about it
You’re ready to embrace your natural capacity to become a role model
Here are 9 takeaways from the conversation
1. The equation of knowledge vs wisdom
Information is at our fingertips, but wisdom? That requires personal experience and reflection.
Understanding the difference transforms our life experiences in midlife and explains why we have more to offer than ever.
“Knowledge is something you accumulate. Wisdom is something you distil.
So if it's a math equation, knowledge would be a plus sign and wisdom would be a division sign. It's the essence of something.
It is taking all of that knowledge, all of that information, and distilling it down to what's essential.”
2. Wisdom comes from what we’ve been through
We can feel ashamed about how tough things are for us. Especially if we think others are doing better.
But our struggles and challenges aren't just obstacles to overcome; they’re the foundation for our future wisdom. As Chip points out,
“Our painful life lessons are the raw material for our future wisdom.
In many ways, wisdom comes from the school of hard knocks, the challenges we've had.”
This perspective helps us see tough times as our valuable teachers.
3. Cultivate a wisdom practice
How often do you reflect on your experiences? Most of us focus on the next thing on our to-do list
But creating an intentional practice can speed up personal growth. Chip shares a powerful weekly ritual he's maintained for decades.
“I've been doing something since age 28.
Each weekend I spend 20 minutes making a list of all my key lessons of the week. They could be personal, professional, spiritual, physical, etc.
Often the lessons were painful.
And then I say, ‘How will it serve me in the future?’”
4. Clear the path for insights
One of the biggest reasons why people join Alptitude, Summercamp, or Vision, is the space they create.
The space to open up a path between our heads, hearts, and guts, to access the deeper wisdom that's been waiting to emerge. As Chip puts it,
“Allow the spiritual plumber to open up the pipe that goes from the head to the heart, to the gut/soul, because that heart to soul pipe is usually pretty clogged.
The moment you start to open that up .. we become a sort of midwife for midlife epiphanies, and new ideas come up that have been stuck down there.”
5. Understand your unconscious patterns
We think that we’re directing our lives, making conscious decisions. But more often than not we’re a passenger, with our unconscious at the wheel.
Tools like the Enneagram help us spot our biases and patterns, allowing us to see ourselves more clearly - and respond accordingly.
“Once you understand the unconscious bias of how you see the world, you can say, ‘Oh God, that's me being performative right now.’
Or, ‘That's me caring too much what other people think about me.’
Or ‘That's me being self-critical to push myself to success.’
Sometimes those are good things, but sometimes they're not. And to understand the dark side of your personality type allows you to transcend it.”
6. You’re already a role model
Leading others goes beyond titles. Chip explained how he experimented by banning the words “manager” and “leader” for a month in his organisation. He asked everyone to replace them with the term “role model.”
“It was miraculous. Leaders recognised that the more senior you are in leadership, the more contagious your emotions, the more contagious your habits.
A CEO is not just a Chief Executive Officer. They're the Chief Emotional Officer because our emotions are contagious.”
The more senior your position? The more your emotional state creates a ripple effect.
7. Know when it's time to step away
We work with many founders, and sometimes the wisest leadership decision is recognising when you're no longer the right person to lead - even if it's a company you built.
Chip knows this realisation first-hand after a near-death experience.
“After 24 years I knew I needed to leave because I was sort of depressed. I didn't want to do that anymore. For the good of the company, I needed to do that.
Even if I wanted to stay, I was not the visionary that I used to be. I was the martyr.”
8. Forget purpose. Be purposeful
Has finding your purpose become a source of stress? You’re not alone. As Chip notes,
“There are a lot of people who freak out because all their friends have a purpose, and ‘I don't have a purpose,’ as if it’s a BMW in the driveway.”
He suggests we focus on the many ways we can live purposefully, treating purpose as a verb, not a noun. And your purpose doesn’t need to come with a capital P, either.
While career accomplishments often define our public identity, having many smaller purposes creates and curates the kind of life that’s well-lived.
“Whether it's being a parent, a political activist, a gardener, or a marathon runner, or being involved in a spiritual community, those ‘small p’ purposes add to a broader tapestry of a life.”
9. Four purpose shortcuts
While major life events can provoke us into reviewing our lives, they don’t have to.
If you're searching for purpose with a big or a small ‘p’, Chip offers four pathways that don't require a crisis to discover:
Something that excites you
Something that agitates you
Something that makes you curious
Something from earlier in your life that you were passionate about that you have neglected.
And who knows? Your second mountain might lie at the end of one of these pathways.
As we move through midlife and beyond, the opportunity to reimagine our lives becomes more apparent.
The skills, experiences, and even the challenges we've faced become the raw materials for crafting a life that brings not just success but deep fulfilment.
Both The Happy Startup School and Chip's Modern Elder Academy share a vision of entrepreneurship as a journey of self-discovery - one that can lead to businesses and lives aligned with our truest selves.
As Chip models through his own life, this is about “growing whole, not just growing old.”
Many thanks to Chip for your time.
You can find him at The Modern Elder Academy, read his NY Times bestseller Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age, and discover his website.
Last call for Alptitude
14-21 June 2025, French Alps
A once-in-a-lifetime retreat in the mountains for 20 leaders that want to level up their impact, create space for reflection and share meaningful experiences in nature with like minds. This is the week that dreams are made of.
Register your interest below
(You'll receive a link to book a quick call to check if it's a good fit for you)
Ready to explore your own midlife renaissance?
Join our community of purpose-driven entrepreneurs who are crafting businesses and lives that feel as good as they look.
Discover our Vision 20/20 small group coaching program, our Alptitude leader’s retreat, or our business retreat for hippies at Summercamp.
