There is a scene near the end of Mad Men that has been living in my mind lately. It appears in “The Milk and Honey Route,” the penultimate episode of the entire series. Don Draper is sitting alone on a simple wooden bench at a literal crossroads. His past is heavy. His sense of identity is shaken. Every illusion he has held onto is slipping away.
He is not in a boardroom. He is not commanding a room or crafting the perfect pitch. He is simply a human being at a crossroads waiting for a bus. Two roads stretch away from him. The world around him is still and quiet. Then Buddy Holly’s song, “Everyday,” begins to play. It is light and gentle almost innocent against the weight of everything happening in his life. Don does not say a word. He simply smiles. It is small and worn but it is real.
And in that moment the crossroads becomes something else entirely. It is not a sign of failure. It is a place of possibility. A reminder that endings are also invitations. A signal that a new chapter might be waiting just beyond the next turn. That scene has always stayed with me and it echoes especially whenever I reach crossroads. The crossroads can sometimes be a place where I feel like a castaway from my own story. It sometimes resonates as place where the past feels louder than the future.
But crossroads are also moments of choice. They remind us that the narrative is not over.
Leaders Are Human First
Leadership can trick us into believing that we need to be composed and clear at all times. But human centeredness asks us to stop pretending. It reminds us that we can feel discouraged. We can feel disconnected. We can feel unsure. We can feel deeply human.
We cannot foster belonging for others if we ignore our own longing.
We cannot create connection for others if we are afraid to name the disconnection inside of us.
We cannot invite others to honor their gifts if we forget the gifts we carry.
When we forget our humanity leadership becomes empty.
When we honor our humanity belonging begins to grow.
Taking Back the Narrative
Lately, I have been wrestling with my narrative. The old version no longer fits yet the new one has not appeared in full shape. That in-between space can make even the strongest leader feel small. It can stir up doubt. It can amplify old wounds. It can convince us that we have failed.
But the narrative is not fixed. It is alive. It breathes.
We have the ability to reclaim it.
We have the ability to reinterpret the past.
We have the ability to decide what comes with us into the next chapter.
Reclaiming a narrative does not require us to erase pain.
It requires us to believe that we are still in the story.
How Might We Move Forward
I have been sitting with a set of big questions. Quiet questions. Honest questions that come from a place of wanting to understand what comes next.
How might we create belonging when we feel lost?
How might we honor our gifts when doubt feels heavy?
How might we acknowledge the seasons that humbled us?
How might we carry on when the path does not reveal itself?
Maybe the answer is simpler than we think.
We choose the next small step that moves us forward.
Not the perfect step.
Not the loudest or most impressive step.
Just the one that points toward healing and growth and connection.
Forward is not about speed. Forward is about intention. There is always a way forward at a crossroads.
A New Narrative Begins With One Step
Crossroads do not require us to know the entire map. They only require us to breathe to rise and to choose. Leaders carry the responsibility of illuminating a future path for others. That same responsibility calls us to illuminate a future path inside ourselves.
We keep showing up.
We keep tuning into the gifts that are still there.
We keep noticing the gifts others bring.
We keep giving ourselves permission to change.
We keep claiming belonging even when we feel like castaways.
Most of all we keep writing the next sentence of our narrative with honest hope and steady courage trusting that more of the story is still waiting to be revealed.
Your Move at the Crossroads
If you find yourself at your own crossroads I hope you remember this. You are not alone. You have not failed. You have not reached the end. You are standing in a place where your narrative can open into something new and meaningful. A place where the horizon stretches in every direction. A place where you get to choose the next chapter.
There is a future waiting that you cannot yet see. But it will meet you as soon as you take the next step toward it.
Leadership Liner Notes: Sean Gaillard 