The Crossing

I watched four human beings leave Earth’s orbit last Tuesday.

I did not catch it on a replay or scroll past it as a headline between meetings. I sat down and watched the Artemis II launch live, from the countdown through the moment Orion cleared the tower, and I did not move for a long time after that.

It has been fifty-three years since anyone traveled beyond low Earth orbit. Fifty-three years since Apollo 17 came home in December of 1972 and the door to the moon quietly closed behind it. For more than half a century, no human being crossed that threshold again. And then, on the first night of April, four astronauts strapped into a capsule smaller than most studio apartments and let themselves be hurled toward something no living person had experienced in their adult memory. Reid Wiseman, Victor Glover, Christina Koch, Jeremy Hansen. Four people who decided the crossing was worth the cost.

I keep thinking about what that felt like. The emotions of it, rather than the physics.

The months of preparation that cannot fully prepare you. The moment the engines ignite and the decision you made in a calm room six months ago becomes irreversible in the body. The vibration. The noise. The point where the atmosphere thins and the blue curve of Earth appears in the window and you realize, in a way you could not have understood from the ground, that there is no version of this that includes turning back.

That is what a real transition feels like.

I have been sitting with the word transition for weeks now, long before the launch. It keeps surfacing in conversations I am having with founders, with executives, with people building things they believe in who have arrived at a point where the next version of their work, or their life, or their identity requires them to leave something familiar behind.

The word gets used lightly. Career transition. Market transition. Digital transformation. We talk about transitions as if they are planned migrations with a clear departure point and a known destination. In practice, they are closer to what happened on that launch pad. You commit before you fully understand what you have committed to, and the rest unfolds in motion.

What I have noticed, in rooms, in advisory conversations, in my own life, is that most people do not get stuck because they lack a plan. They get stuck because they are waiting to feel ready. And readiness, in the way we imagine it, does not come. It does not arrive before the launch, before the pivot, before the conversation you have been avoiding for months.

The astronauts aboard Orion trained for years. They studied failure scenarios, practiced abort sequences, simulated every phase of the mission until the movements became automatic. And still, I am certain of this, there was a moment on that pad where the knowledge and the preparation met something older and less rational. The part of the brain that knows you are about to do something you cannot undo.

Courage is not the absence of that feeling. It is the decision that happens alongside it.

A few weeks ago, I was in a conversation with a founder who had spent 18 months building a product that was gaining traction, real revenue, early signs of product-market fit. By every external measure, things were working. And she sat across from me and said, quietly, that she was terrified.

The fear was not about failure. It was about the next phase.

The version of the company that was coming, the one with a larger team, more complex operations, higher stakes, scrutiny that arrives once people start paying real attention, required her to become someone she had not been yet. The scrappy, intuitive, hands-on-everything version of herself that had built the first chapter was not the person who could carry the second one. She knew this. And knowing it did not make the transition easier.

I recognized that feeling because I have lived inside it. The transition from one version of yourself to the next does not happen in a single moment of clarity. It happens in a long, disorienting stretch where you are no longer who you were but not yet who you are becoming. You are mid-flight. The atmosphere is thinning. And the temptation to retreat to the familiar is enormous, driven less by the familiar being better and more by it being known.

The hardest transitions are not the ones that ask you to do something new. They are the ones that ask you to stop being someone you have already proven you can be.

What strikes me most about the Artemis program is not the technology. It is the gap.

Fifty-three years. We went to the moon, and then we stopped going. The knowledge did not disappear. The science did not vanish. We stopped because the will shifted, the funding moved, the political moment passed, and the risk calculus changed. We told ourselves we would go back. We built plans. We announced timelines. And for more than five decades, we stayed in low Earth orbit, circling close to home.

I see this pattern everywhere. In organizations that talk about transformation but keep circling the same operational altitude. Founders who know the next chapter requires a leap but keep optimizing the current one instead. In my own career, if I am being honest, the years where I knew a transition was coming and chose the comfort of preparation over the discomfort of movement.

The gap is never about capability. It is about the accumulated weight of reasons not to go.

Every year you do not make the crossing, the crossing feels larger. The risk feels more real. The distance between where you are and where you need to be stretches until it looks insurmountable. And then someone, four someones strapped into a capsule, decides to go anyway. The risk had not diminished. The cost of staying had simply become visible.

Victor Glover is the first Black astronaut assigned to a lunar mission. Christina Koch holds the record for the longest single spaceflight by a woman. Jeremy Hansen is the first Canadian to travel to the moon. These are not just technical milestones. They are human ones. They represent transitions that took generations, shaped less by engineering than by who gets to be in the room, who gets to sit in the capsule, who gets to be part of the story.

The transitions we are living through right now, in AI, in entrepreneurship, in the broader reshaping of how we work and build and define ourselves, are not only technological. They are personal and touch our core identity. They ask us to cross thresholds we did not choose and cannot fully prepare for.

The founder sitting across from me was not facing a business problem. She was facing an identity problem. The astronauts aboard Orion were not simply executing a mission plan. They were doing something that required them to trust the version of themselves they had not yet been tested as. That is the part no preparation fully covers. The part that makes transitions terrifying and necessary and, when you look back on them, the only moments that actually mattered.

I used to think courage was a trait. Something you either had or you didn’t, something that lived in certain people and not in others. I have spent enough time in rooms with founders and leaders to know that is not true. Courage is not a trait. It is a practice. It shows up in the moment you decide to move even though the fear has not left.

The Artemis II crew will loop around the far side of the moon, the part you cannot see from Earth, the part where communication with mission control goes silent for a stretch of minutes that must feel much longer than they are. And then they will come back. They will re-enter the atmosphere, endure the heat and the deceleration, and land in the Pacific Ocean, changed.

That is what transitions do. They take you to the far side of something. Communication gets thin. The familiar signals disappear. You are, for a period of time, on your own with whatever you brought with you. Your training, your instincts, the relationships you built before the crossing. And then you come back. But you do not come back the same.

I am in my own crossing right now. The work I am doing with SmartHaus, the questions I have been asking for three years about governance and quality and the missing layer, they have brought me to a threshold I can see clearly but have not fully stepped through. The next chapter requires something from me that the last chapter did not. I know this. And I am moving anyway.

I am moving because I have watched what happens when people wait for readiness that never arrives. They stay in low Earth orbit and circle. They optimize what they already know. And the gap grows.

The courage is not in the arrival. It is in the leaving.

I watched those four astronauts disappear into the sky last Tuesday and I felt something I had not expected. It was not quite inspiration. It was recognition. The recognition that every meaningful transition in a life, whether leaving a role, starting a company, becoming a different kind of leader, or admitting that the version of you that got here is not the version that gets you there, begins with the same terrifying act. You let go of the ground.

The moon has been there for 53 years, waiting. Some crossings cannot be optimized or scheduled or made comfortable. They can only be made.

I hope you are making yours.

Reaching for the far side,

Yen