I was sitting on a mattress on the floor of my cold, unfinished basement, reading beneath a bare lightbulb dangling from exposed wires. Renovations to my newly purchased post-divorce house had exiled me downstairs, where even the dogs couldn’t visit. Outside, the Chicago winter was 20 below zero, and the wind seeped through the windows, gently swinging the bulb above my head.
Just two years earlier, a string of investment wins had landed me on a Top 100 VC list. My divorce had been amicable, yet here I was, freezing and alone, feeling as “stripped to the studs” as my house.
I remember thinking, “Well, I’ve had a good run. Now I just need to wait out the clock until the Big Guy takes me upstairs.”
I’d stopped imagining a future worth getting excited about. The game felt over. My marriage, career, home, and daily life had all changed, leaving me adrift, unsure what came next.
Ironically, I was standing at the threshold of one of the most extraordinary chapters of my life.
“We must be willing to get rid of the life we’ve planned, so as to have the life that is waiting for us. The old skin has to be shed before the new one can come.”
- Joseph Campbell, A Joseph Campbell Companion
But often, the hardest part of transformation is letting go of the old, the life we thought we were supposed to live. We may be willing to endure the struggle, but are we willing to release the identities, expectations, relationships, and dreams that defined our old life?
What if our greatest obstacle to our next chapter isn’t what we’ve
lost, but what we’re Unwilling to Release?
There is a particular kind of sadness that comes not from losing something we had, but from losing something we believed we were going to have. We lost the job, a marriage, our health, a loved one or a friendship. We expected our career to go a certain way, a marriage to live happily ever after, our family would look and feel a certain way.
We don’t just grieve what is gone. We grieve the future we had
already written in our minds.
So we cling. We try harder. We replay conversations, seek clarity, and grasp for control. We spend more energy trying to preserve a life that no longer fits than creating one that might truly bring us alive.
The Hardest Thing to Lose Is Actually Our Identity
What if letting go isn’t about losing ourselves, but
finally discovering who we really are?
There is a beautiful Buddhist parable about the Golden Buddha, a magnificent golden statue covered in clay to protect it from invading armies. Generations passed, and eventually people forgot what lay underneath. Only when the clay cracked and fell off, did the villagers and monks rediscovered the Gold.
There is parallel in the Christian concept of Imago Dei, that we are created in the image of God, with an inherent dignity and worth that precedes anything we accomplish.
Yet somewhere along the way, we learn that our worth comes from our spouse, community, job title, bank account, or others’ approval. To belong in our families, schools, workplaces, and relationships, we believe we must Become Something Else. Something Better.
We forget that we were Born Golden. Our natural gifts, strengths, and inherent worth were there all along. Jim Collins calls some of these enduring qualities our “Embeds”, the strengths and dispositions woven into who we are and cannot be taken away.
Perhaps our task isn’t to become someone else, but to shed the clay, the
bullshit masks, and reclaim who we’ve always been.
But that’s terrifying. What if our authentic selves aren’t enough? What if shedding those masks gets us kicked out of the tribe? How do we do this and pay the bills?
So we resist, even when life is practically screaming at us to change. As my friend and mentor Jerry Colonna once put it:
Eventually life grabs you by the throat and says, ‘I’ve been whispering to you and you won’t listen. Listen now, motherfucker.’
Facing the Dragon
In Campbell’s Hero’s Journey, the protagonist must eventually face the dragon. We imagine it as something external: a failed business, a broken relationship, a lost fortune, an uncertain future. But often, the real dragon lives within:
I’m not enough. There’s not enough. I’m not safe.
I must achieve to be worthy. Give to be loved. Please others to belong. Control to feel safe.
I know this dragon well. Achievement, ambition, and service have brought extraordinary meaning and relationships into my life. But growing up, I learned that doing well earned my mother’s approval and offered her a welcome respite from her anxiety. Somewhere along the way, achievement and giving became intertwined with being loved.
Which raises an uncomfortable question:
Am I achieving and serving because it brings me alive, or because I believe I must earn my worth, approval, or love?
The same behavior, driven by two very different motivations, can be the difference between the Good Life and the Rat Race.
We can work hard from passion or fear of irrelevance. Give generously from love or fear of rejection. Pursue excellence to express our gifts or silence the voice insisting we’re still not enough.
But our dragons aren’t always about worthiness. Sometimes they’re about survival and security. How will I pay the bills? What if I lose my financial independence? What if I let go of this relationship and never find love again? What if the next chapter is worse than the last?
These aren’t imaginary fears. Financial obligations, uncertainty, and the need for stability are real. Courage doesn’t mean ignoring those realities. It means distinguishing what we genuinely need to protect from what fear is keeping us from releasing.
And sometimes we hold on simply because something was beautiful, meaningful, or worth fighting for. Letting go doesn’t diminish that.
Perhaps the first step toward letting go isn’t releasing what we’re holding onto. It’s understanding what we’re afraid will happen if we do.
The Courage to Let Go
The butterfly must leave the chrysalis to fly. Yet we want the freedom of a new life without the vulnerability and uncertainty of leaving the old one behind. We long for what comes next while clinging to what feels familiar and safe.
The next chapter isn’t guaranteed to be better. But it may hold extraordinary possibilities we cannot yet imagine. I know from experience that getting there can be uncomfortable, terrifying, and, at times, brutal.
Letting go is not the same as giving up.
It doesn’t mean the marriage wasn’t meaningful, the career wasn’t worthwhile, or the dreams were foolish. It doesn’t mean denying the love, the beauty, the mistakes, or the loss. It means recognizing that some things were meant for a reason or a season, but not a lifetime.
It means honoring what was without insisting that it must still be.
And it means allowing ourselves to feel the sadness. We don’t need to outrun grief, intellectualize it, or immediately turn it into a lesson. Some things deserve to be mourned. Some chapters were beautiful even if they ended differently than we hoped.
But sadness and hope can coexist.
We can be grateful for what was, grieve what will never be, and still feel excitement about what might come next.
Perhaps the most courageous thing we can say is:
That chapter mattered. I loved parts of it deeply. I wish some things had been different. But I don’t have to keep living in a chapter that’s ended. I’m ready to discover what comes next and more of who I truly am.
The Northstar: What Brings You Alive?
Since we are taught to define ourselves by external markers, external validations and external milestones, what becomes our Northstar when we shed much of this. The answer is simple and timeless. Simply ask:
DOES THIS BRING ME ALIVE?
Not: Will this impress others?
Not: Is this what someone in my position is supposed to do?
Not: Will this earn me approval or love?
Instead: Does this energize me, deepen my connections, express my strengths, and give my life meaning?
The Good Life, as I’ve come to understand it, isn’t a destination or a checklist of accomplishments. It’s a life of increasing alignment between who we truly are, what we value, how we love, and what we choose to do with our precious time.
This doesn’t mean chasing pleasure or avoiding discomfort. Some of the things that bring us most alive: raising children, building something meaningful, loving deeply, serving others, also demand sacrifice, discipline, and courage.
It might mean rediscovering an old passion. Building something new. Finding the courage to love again. Spending more time with people who appreciate our authentic selves. Saying no to obligations driven by guilt or approval, and yes to experiences that fill us with curiosity and purpose.
And it means making room for the unexpected.
When we stop forcing life into the shape of our old expectations, we become open to possibilities we couldn’t have planned. We notice the people who bring out our best, the experiences that energize us, the strengths waiting to be expressed, and the dreams quietly taking shape.
We don’t need to know exactly where the road leads.
We just need to know who’s walking it.
Simple Letting Go framework:
A Small Exercise in Letting Go
You won’t figure it all out in advance. Much of it will be revealed along the way.
You don’t need a five-year plan. You don’t need to know exactly who you’re becoming. You need only enough faith to loosen your grip on what no longer serves you, and enough courage to take the next step.
If you’re navigating a transition, take ten quiet minutes to answer five questions:
What am I holding onto that no longer serves me? What identity, expectation, relationship, or imagined future am I struggling to release?
What am I afraid of? What do I fear losing—my worth, love, belonging, financial security, or sense of safety?
What is holding on really costing me? My energy, peace, time, relationships, or opportunities? How might life feel different if I let go?
What brings me alive? Which people, activities, and experiences reconnect me with my authentic self?
What is one courageous next step? What small action can I take this week toward the life I want to live?
The life waiting for you may not be the one you planned.
Perhaps becoming isn’t about creating a better version of ourselves. Perhaps it’s about finally allowing the person we’ve always been to emerge.
Now, knock off that mud.