The Midlife Reorientation - a User's Guide
The Midlife Reorientation - a User's Guide
"WTF is happening to me?" and How to navigate the midlife transition with grace
Welcome Entrepreneurs, I'm so glad you're here.
And welcome back to Substack! Funny enough, I’ve already seen more subscriber growth on Substack in the two weeks since posting that announcement than I saw in the last two months on Mailchimp. I wonder why…👇
Anyway, onto this week’s essay. A guide to how to do midlife right, as an entrepreneur.
The Midlife Reorientation — A User’s Guide
“Man has two lives. The second one begins when he realizes he has only one.”
— Confucius
Much of my work is with entrepreneurs at midlife. At that very specific point (not necessarily tied to age), they find themselves struggling for the first time to answer two important questions - who am I? and why am I here?
Up until this point, answering these questions has been as easy as falling off a log.
Who am I? – I’m the CEO and founder of XYZ company
Why am I here? – to make XYZ company successful
But then there’s a break in the action - an exit, a failure, an identity shift - and all of a sudden, the answers aren’t so clear anymore. While the rest of the world has been asking and answering these questions regularly, slowly orienting by degrees to the life they’re meant to live, entrepreneurs’ enmeshment with their companies makes the answers seem self-evident for years, allowing unexamined questions to build up until they all come rushing back at once.
Brene Brown captures the midlife process for most people with her article “the Midlife Unraveling.” But for entrepreneurs, the stark shift in volume really makes it occur as a crisis.
I’m drawn to this work for two reasons.
First, I went through my own reorientation, and it was the most difficult, most important transformation of my life to date. It literally gave me my life, my work, my relationship with the Universe, and the deepest relationships with those around me, which are much more numerous and satisfying than I ever expected. So I understand the importance of it.
And second, later stage entrepreneurs have enormous capacity to effect significant change, so this reorientation carries incredible leverage. If one successful entrepreneur does the work to come alive and step fully into their life, it immediately impacts their team, their company, their customers, and their little corner of the world. I think of it as “trickle-down consciousness.”
I help a dozen or so entrepreneurs at a time navigate this process more gracefully, with less collateral damage to their lives, but there’s no way I’ll ever be able to satisfy the demand. And if you’re going through it, the demand is as painful as anything you’ve ever experienced. Not dealing with it is not an option.
So for those going through the process with whom I can’t work directly, I provide the model below as a touchstone.
So. What the fuck is going on?
It’s a reasonable question. When founders reach this stage (usually sometime mid-thirties through late forties), everything feels like it’s falling apart, and yet nothing feels like it matters. It’s holistic and disorienting. What the fuck is going on, indeed.
That’s what I hope to answer here.
At midlife, all the chaos and rethinking centers on two profound identity shifts. They can take place simultaneously or in rapid succession.
First, you shift from an external, acquisition-based identity, to an internal, expression-based identity. And second, you shift the focus of identity from the individual to the collective.
See this image for a map of how this works:
These shifts in identity would be hard enough on their own, but for those of us living in the consumerist, individualist West, they also run directly opposite to our culture.
Movin' eight miles a minute / For months at a time / Breakin' all of the rules that would bend / I began to find myself searchin' / Searchin' for shelter again and again
“Against the Wind” – Bob Seger
These identity shifts are a doozy. Let’s start by breaking down the first one.
From acquisition to expression
During the first half of life, we acquire our identities from worldly things (money, stuff, status, etc). We build and buttress our idea of who we are based on our accomplishments, the roles we play, and the relationships we have. This is how we test ourselves and learn what we’re capable of. Without this phase we’d never know just how much capacity we have (we also wouldn’t have the actual, financial/skillful capacities we develop over that time), and in the second half of life, we would have much less capacity. In other words, acquisition in early life is a feature not a bug.
Some of us stay in the first half of life for our entire lives, building taller and taller towers of success, twisting ourselves into pretzels to become the ideal citizen and never questioning why. But when done well, once we’ve learned what we’re capable of through the first half of life, in the second half we let go of all the inherited aspects of identity, and we get to know ourselves deeply. Our True Self. The person underneath all the roles, accomplishments, and relationships.
This happens in two stages.
Part one requires a reorientation, which, because nobody reorients because they want to, requires pain. People typically enter into stage one of this reorientation because of either a fall or failure, or at the empty end of tremendous material success. Either way, the result is the same – a wholesale reckoning with what they thought was important.
For entrepreneurs, it usually means letting go of the outward success-chasing, however that word is defined for them, and instead looking inward. Finding what is truly important by looking beyond or underneath all the things they thought were important. This is what is meant by dying a large number of small deaths, to earn the privilege of living a bigger, more meaningful life.
You need a very strong container to hold the contents and contradictions that arrive later in life. You ironically need a very strong ego structure to let go of your ego. You need to struggle with the rules more than a bit before you throw them out. You only internalize values by butting up against external values for a while. All of this builds the strong self that can… “die to itself.” — Richard Rohr
If all that sounds dramatic, it’s because it is. This work is the most lonely, isolating, and crazy-making I’ve done in my life, and I see the same in the clients I work with. Which is why it can be so helpful to have a fellow traveler on your journey. Without someone who’s been to the other side helping you take the next step, it’s way too tempting to turn back. To just build something bigger, thinking the size of your accomplishment was the issue.
Either way, after significant effort to let go of all the things we thought we were, if we’re lucky, we get to meet our True Self, our Soul, or whatever you want to call the unique imprint at the core of our being. Underneath all the things we’ve been trying to be. This usually doesn’t occur as a list of values, or a mission statement, because, by definition, the minute we objectify the self in such a way, it immediately stops being our true self and starts being an object to interact with. You recognize your true self intuitively, not intellectually. Like love.
That’s step one. And as I wrote about vocation, step one never ends.
Step two is following what you find inside—both beautiful and ugly—and expressing that Self into the world, honestly and thoroughly, with all the skills you've amassed during the first half of life. Even if you don’t fully understand it. Even if you don’t want to at first. Following it, and trusting that expressing what’s inside you to help your fellow travelers is the true work of your life.
There is a vitality, a life force, an energy, a quickening that is translated through you into action, and because there is only one of you in all of time, this expression is unique. And if you block it, it will never exist through any other medium and it will be lost. The world will not have it. It is not your business to determine how good it is nor how valuable nor how it compares with other expressions. It is your business to keep it yours clearly and directly, to keep the channel open. You do not even have to believe in yourself or your work. You have to keep yourself open and aware to the urges that motivate you. Keep the channel open. – Martha Graham
Amidst a culture that deifies acquisition and consumption, it takes a certain amount of seasoning to realize that because you will only live once, and you can’t take anything with you at the end, the true measure of success is what you leave behind.
It takes something to sacrifice what everyone else is chasing, for what is uniquely yours to express. But there is nothing more tragic than a song not sung.
From the individual to the collective
“From the time we are born, we go about our lives looking at the world with the eyes of “me,” hearing sounds through the ears of “me,” and pursuing the happiness of “me.” This is so for all people. When one knows real love, however, the subject of life changes from “me” to “us.” It allows one to live by completely new guidelines that are of neither self-interest nor other-interest.” – Ichiro Kishimi & Fumitake Koga
As if transitioning from acquiring your identity to expressing it isn’t complex enough, there’s another axis to traverse.
The second part of the transition is this: shifting the locus of the ego from yourself the individual to some greater “us.” Be that your family, your community, your country or the world.
For the first couple decades of our life (give or take), our identity, first and foremost, is as a child. We are who we are in response to (either pulling toward or pushing against) our families of origin and/or our communities. If our family is poor, that means we as individuals are poor. If they are mean, we are mean. It’s not until the teenage years that we start to establish our independence. Our own identities.
What starts in our teenage years, the shifting of identity from “we” to “I” continues all the way up until midlife. The act of pushing against our groups of origin is what allows us to figure out who we are as individuals. Through this process we learn individuality, boundaries, responsibility, and our own, personal values. By pushing against the value structures we were born into, we develop the ability to do unpopular things, to think for ourselves, and we cultivate an understanding of our capacity to affect change – both how strong we can be, and the limits of that strength.
Developing this strong sense of “I” is the purpose of the first half of life, and it’s wonderful and useful in its own right. But, it’s also a phase that is eventually transcended, at midlife, on the way to a broader, personal, sense of “us.”
It’s worth noting that the first shift – from acquisition to expression – often happens before, and indeed causes, the second – from individual to collective. Because when you look deeply into who you are, and if you do that exploration honestly, what you find is that you aren’t who you think you are.
As you see the external origins of your cherished beliefs and values, you learn that you don’t actually have the degree of free will you always expected. The more you zoom into yourself, the more clearly you see that you as an individual are inseparable from the world around you. Your family, your friends, your community. I’ve heard it said that you’re the average of the five people you spend the most time with. Well, they are too, and that fact connects us all. You aren’t an individual at all. You are actually part of a massive and holistic web of the universe.
Once you fully grok this (which like the first step often takes some serious work because it’s so countercultural), your identity starts to shift to include the world around you. Your well formed “I” is transcended and included within a growing sense of a personal “We,” which can refer to anything from the scale of the entire world, to that of a family or community. Anecdotally, in my work with founders I often see people who in their first half of life measured their impact according to the largest possible scale (millions of users, say), shift to a much more local focus as they mature. This is the transition from an “I” who needs to put a dent in the universe, to a “we” for whom there are many opportunities to make a difference (perhaps part of why so many startup elders begin seeding their communities with angel investments).
What gives? You might be asking. We spend the whole of our first half of life trying to break away from our groups and establish ourselves as individuals. Only to go back to being defined within groups?
Yes. But whereas the “We” of our early life refers to the groups into which we’re born, our family, faith, and friends of origin, the “We” of the second half of life grounds us firmly in the groups born out of who we are as individuals. The people, places, and causes about which we choose to make our lives. This is what T.S. Eliot meant when he wrote: “We shall not cease from exploration / And the end of all our exploring / Will be to arrive where we started / And know the place for the first time.”
The opportunity for entrepreneurs at midlife
At our particular moment in history we live in a consumerist, individualist society. Everything around us supports the solo striving that is characteristic of the first half of life, and as a result we’ve achieved more than we ever could have imagined. But what even the most successful among us have not achieved is lasting contentment. See Tony Hseih, Jim Carrey, etc.
“I think everybody should get rich and famous and do everything they ever dreamed of, so they can see that it's not the answer.” – Jim Carrey
But we haven’t always lived in this zeitgeist. Consider the 99.9% of human history in which we lived communally, in towns and villages. Close knit communities, anchored by those in their second half of life, in which everyone had their place and everyone contributed to something more important than their individual selves.
For most of human history, our communities were led by elders. That is the opportunity for entrepreneurs making their journey through midlife today.
Like a village elder, an entrepreneur in their second half of life finds their place not by acquiring, but by expressing their hard earned time, talents, and treasure. And accomplishes great things, not to buttress their individual pride or status, but for the good of the village.
Things I read this week
One: Rethinking the narrative of success and spirituality
People think that being spiritual will cost you success. And that trying to become materially successful means you can’t be spiritual. I’ve found it’s the opposite, and the path to material success flows most easily through spirituality. So has Scott Britton (who incidentally I’ve met and his work is very cool).
Two: AI Powered Journaling
I’m a huge Morning Pages Stan. I journal even on days I don’t meditate. And I’m very curious about how AI can leverage my journals to help me understand myself better. I haven’t taken the plunge here, but I sense there’s a “yet” behind that sentence.
Three: The Value of Surrender
I’ve been consciously surrendering to the flow of my life for a few years now, and am making more money, having more fun, and feeling more alive than ever. While I still have a bit of a hangup “selling” the value of this way of living, I love when others do, like Sasha does here.
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
Here are a few of my favorites:
The secret to leadership (why authentic leadership is simply more effective)
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