Crucibles, Chrysalis, and the Biology of Rebirth

Emerging from the Shell of Who You Used to Be

I have a profound, stubborn faith in a divine belief that the universe operates with a quiet, benevolent intention. I believe that even when the world feels chaotic, when our familiar grounding and dreams have shifted or dissolved, that Life is not just working for us but rather through us, if we let it.

This quote from St. Augustine is so relevant to both our own life journeys and my world as a venture capitalist.

Faith is to believe what you do not see; the reward of this faith is to see what you believe.

This describes both our own life journeys and my world as a venture capitalist. If you can see it, it isn’t the revolutionary, massive winner. You have to back a vision of the future before the data exists to prove it right or safe. If you wait for the proof, the opportunity is gone.

When I seeded Dollar Shave Club, the company was just four people in a crowded accelerator bullpen, before the now famous launch video dropped. The existing data told us that giants like Gillette owned the market.

But we had a deep faith in our core theme—a conviction that offline incumbents were sleepy and ill-equipped to compete online. We had faith in Mike’s brilliant flair for storytelling and his exclusive, advantageous supply deal. We backed an invisible future. Our reward for that faith was a $1 billion exit to Unilever.

Great companies, great love stories, great careers and strong families share this single truth: they are willed into existence through perseverance. None of them come with a guarantee. Each is a radical leap of faith—especially when you hit turbulent air and begin to question the flight.

But demanding faith in an energizing, beautiful future is the only way forward. There is no certainty in life—only the willingness to step into the dark and build anyway.

Dark Night of the Soul

As an investor, a coach, and a human being, I live daily in the world of “destructive creation.” I get a front-row seat to the messy, painful periods of change we all go through. We call them many things: a major transition, a career pivot, a “life quake.”

When you are in the thick of it, it can feel completely overwhelming. Your plans are in disarray, your old routines don’t work anymore, your supports & friends & motivations change and your soul feels a bit on fire. In those moments, it’s completely natural to feel exhausted, to want to pull the covers over your head, or to desperately wish things could just go back to the way they were.

If you are feeling that weight right now, hear this: You have not failed. You are just inside the chrysalis. And the squeeze you are feeling is actually a beautiful sign of what’s to come.

The Real Lesson of the Butterfly

There is a well-known story about a man watching a butterfly struggle to emerge through a tiny tear in its chrysalis. Out of deep kindness and a desire to stop its suffering, he takes a pair of scissors and gently snips the opening to make its escape easy.

The butterfly crawls out effortlessly. But its body is swollen and its wings are shriveled. It spends the rest of its short life bloated and grounded, never able to fly.

What the well-meaning man didn’t understand is the beautiful physics of breakthrough. The intense pressure of those cocoon walls is biologically mandatory. That tight squeeze is exactly what forces the fluid out of the insect’s body and into the veins of its wings. Without the struggle, the wings never develop the strength, the structure, or the capacity to lift off.

The pressure isn’t there to crush you. It’s there to burn away the old, to remove that which doesn’t serve you anymore, to build your muscle, to focus you on your gifts vs your obligations and to prepare you to become a butterfly.

Look for what new freedoms or opportunities have emerged in front of you and seize them. In venture, we say: Never waste a good crisis

When the overwhelm hits, our instinct is to look for an easy out, to numb the discomfort, or to busily distract ourselves so we don’t have to feel the shift. But bypassing the friction only keeps us trapped. To get to the beauty of your next chapter, you have to give yourself permission to dream and to trust and embrace the squeeze.

Fear constricts & clings to the past and fights for survival. Courage steps into the fear and architects the next chapter, then takes small steps forward. Courage has faith in that you cannot see.

The Reversal of Desire

To move through that tiny opening into your new life, it takes a counter-intuitive shift in perspective. My coach, Phil Stutz, talks about a tool called the Reversal of Desire.

Instead of shrinking back from the overwhelming friction of your transition, you learn to gently pivot, face it, and say to yourself:

“Bring it on. This pressure is how I build my wings.”

This isn’t about toxic positivity or ignoring your pain; it is about mastering your fears. It’s exactly what Aristotle meant when he called courage the gateway virtue—because it is the act of taking action before you have all the evidence that things will work out.

When you’re overwhelmed, you can’t wait until you “feel” perfectly confident, have no anxiety or are ready to move forward. You take one small step in the dark, and the confidence follows.

The sequence of growth is always:

Faith → Action → Feeling/Confidence

Squeezing Forward: The Three-Tier Protocol

If you are currently in the tightest, darkest part of your own cocoon, you don’t have to figure out the whole sky. You just need to focus on what Phil calls the Life Force Pyramid: Body, People, Self. Don’t think…move & do. When everything else feels out of control, you rebuild from the bottom up using three simple tiers of micro-transactions:

• 1. Relationship to Body (eat, sleep, move): When you are trapped in a loop of mental and emotional overwhelm, the quickest way out is physical movement. Do not overcomplicate this. You don’t need a massive workout; just change your state. Get sleep. Go for a morning walk, get out on a hike, hit a tennis ball, or just stretch on the floor. Do Breathwork. Get the body in motion to pump the blood into those wings.

• 2. Relationship to Others: When we are hurting, our primal instinct is to isolate, to pull the covers up, and to hide until we “have it all figured out.” Fight that urge with everything you have. Do not pull away from humanity and the people who love you right now. You don’t need to show up perfectly; you just need to lean in. They will love you just as you are…especially if you let them see what you are going through. Reach out to a trusted friend, grab a coffee, just smile & be with your partner in the quiet. Connection is the ultimate antidote to the dark night of the soul…find someone to go through the chrysalis with you, not alone.

• 3. Relationship to Self: Once the body is moving and you are supported by your tribe, turn inward. Get curious about patterns and beliefs that don’t serve you. Reconnect with your true essence. Breathe, ground yourself, and look honestly at the transition. Work with a therapist or a coach. Journal it out without judgment.

• As you look inward, ask yourself:

  • What old story is leaving? Why has this chapter run its course?

  • What limiting or false beliefs are keeping me small? How am I interpreting things in a disempowering way? (not enough, not relevant, discarded, etc)

  • How can I love more? As Rumi wrote: “Your task is not to seek for love, but merely to seek and find all the barriers within yourself that you have built against it.”

  • What lessons did I learn? What strengths have I rediscovered?

  • What beautiful new freedoms are actually becoming available to me now?

  • And, who (what butterfly) am I now becoming as I shed the cocoon?

Pema Chodron once wrote, “Nothing ever goes away until it has taught us what we need to know.”

If the universe is squeezing you right now, breathe through the overwhelm and trust the process. Lean into your people, move your body, and take it one micro-transaction at a time.

The walls aren’t closing in on you. They are just pushing the life into your wings so you can finally fly.