𝐓𝐡𝐞 𝐌𝐨𝐫𝐧𝐢𝐧𝐠 𝐖𝐚𝐬 𝐍𝐨𝐭 𝐚 𝐋𝐢𝐞𝑆𝑜𝑚𝑒 𝐸𝑛𝑐𝑜𝑢𝑛𝑡𝑒𝑟𝑠 𝐵𝑒𝑙𝑜𝑛𝑔 𝑡𝑜 𝑡ℎ𝑒 𝐴𝑓𝑡𝑒𝑟𝑛𝑜𝑜𝑛

There is a scene in the movie 𝐺𝑜𝑜𝑑 𝑊𝑖𝑙𝑙 𝐻𝑢𝑛𝑡𝑖𝑛𝑔 that has stayed with me for years.

A young Will Hunting sits on a park bench with his therapist, Sean Maguire.

Will is brilliant. He can quote books, solve impossible problems, and intellectually dismantle almost anyone who stands in front of him.

To borrow one memorable line from the scene, Sean tells Will that he may know everything about the Sistine Chapel except "𝑤ℎ𝑎𝑡 𝑖𝑡 𝑠𝑚𝑒𝑙𝑙𝑠 𝑙𝑖𝑘𝑒."

Then Sean points to something deeper. Will can quote sonnets from Shakespeare, but he has never surrendered himself to love.

That he can discuss suffering but has not yet allowed life to break open his carefully constructed certainties.

The scene is powerful not because Sean wins an argument.

He doesn't.

It is powerful because something else happens.

Will is not merely spoken to.

He is met.

Or perhaps more accurately, he is encountered — not as a problem to be solved, but as a whole person whose defenses, brilliance, wounds, and possibilities are all somehow seen at once.

Perhaps the first time, someone meets him beneath the intelligence, beneath the performance, beneath the identity he has spent years constructing and defending.

There is a difference between knowing about a thing and being changed by the encounter with it. Between a conversation that helps us become better at being who we already are — and one that changes what becomes possible.

Most leadership development is built for the first. The feedback, the frameworks, the self-improvement tools, the competency models, the performance coaching that refines a self we have already settled into. This work is useful. I spent much of my career inside it, and I am not against it.

Yet many of the moments that genuinely shaped me seemed to belong somewhere else.

Some of them were conversations. And some of them — I am aware of the irony, having just invoked a scene about the limits of book-knowledge — were books.

Some were simply questions that stopped me in my tracks.

Some were encounters with people I met only briefly.

By encounter, I simply mean a meaningful meeting with a person, a book, an idea, a question, an event, or even a previously unseen part of oneself.

Life is full of such encounters. Some diminish us. Some leave us unchanged.

And some enlarge us.

This blog is an inquiry into the third kind.

The Monday morning after I stepped away from a long career in Human Resources across engineering, R&D, and manufacturing, I found myself in the company of James Hollis’s Finding Meaning in the Second Half of Life.

Somewhere in those pages, a question rose and woke me up a second time — a question that has stayed with me ever since:

𝑾𝒉𝒐𝒔𝒆 𝒍𝒊𝒇𝒆 𝒉𝒂𝒗𝒆 𝒚𝒐𝒖 𝒃𝒆𝒆𝒏 𝒍𝒊𝒗𝒊𝒏𝒈?

I didn’t have a comfortable answer.

For most of my working life, I had treated every role I held 𝑎𝑠 𝑡ℎ𝑒 𝑜𝑛𝑙𝑦 𝑖𝑑𝑒𝑛𝑡𝑖𝑡𝑦 𝐼 ℎ𝑎𝑑.

Each job felt like the only way to be. 𝗜 𝘄𝗮𝘀 𝘁𝗵𝗲 𝗿𝗼𝗹𝗲.

But over time, as I entered the worlds of coaching, Gestalt, adult development, dialogue, systems thinking, and deeper inner work, I began to notice something.

The roles had shaped me.

But the stories I had been living were not the only stories available. The identities I had inherited and constructed were not the whole self.

I began to see how pervasive and seductive those roles had become. I saw the cracks, and the shadows I had not wanted to face.

Then something shifted further: I realized the cracks and shadows were part of me too.

𝑇ℎ𝑎𝑡 𝑙𝑖𝑓𝑒 𝑖𝑠 𝑎 𝑙𝑜𝑛𝑔 𝑠𝑒𝑟𝑖𝑒𝑠 𝑜𝑓 𝑒𝑛𝑐𝑜𝑢𝑛𝑡𝑒𝑟𝑠 𝑤𝑖𝑡ℎ 𝑜𝑛𝑒'𝑠 𝑜𝑤𝑛 𝑑𝑖𝑓𝑓𝑒𝑟𝑒𝑛𝑡 𝑠𝑒𝑙𝑣𝑒𝑠 𝑎𝑛𝑑 𝑑𝑖𝑓𝑓𝑒𝑟𝑒𝑛𝑡 𝑡𝑟𝑢𝑡ℎ𝑠.

To come to this point may take a lifetime. Carl Jung wrote that, "𝘄𝗲 𝗰𝗮𝗻𝗻𝗼𝘁 𝗹𝗶𝘃𝗲 𝘁𝗵𝗲 𝗮𝗳𝘁𝗲𝗿𝗻𝗼𝗼𝗻 𝗼𝗳 𝗹𝗶𝗳𝗲 𝗮𝗰𝗰𝗼𝗿𝗱𝗶𝗻𝗴 𝘁𝗼 𝘁𝗵𝗲 𝗽𝗿𝗼𝗴𝗿𝗮𝗺 𝗼𝗳 𝗹𝗶𝗳𝗲'𝘀 𝗺𝗼𝗿𝗻𝗶𝗻𝗴; 𝗳𝗼𝗿 𝘄𝗵𝗮𝘁 𝗶𝗻 𝘁𝗵𝗲 𝗺𝗼𝗿𝗻𝗶𝗻𝗴 𝘄𝗮𝘀 𝘁𝗿𝘂𝗲 𝘄𝗶𝗹𝗹 𝗶𝗻 𝘁𝗵𝗲 𝗲𝘃𝗲𝗻𝗶𝗻𝗴 𝗯𝗲𝗰𝗼𝗺𝗲 𝗮 𝗹𝗶𝗲"

Peter Block, reflecting on the same idea, said it allowed him to accept a radical shift in his later years without regret for his younger days — without thinking his early pursuits had been a mistake.

𝑻𝒉𝒆 𝒎𝒐𝒓𝒏𝒊𝒏𝒈 𝒘𝒂𝒔 𝒏𝒐𝒕 𝒂 𝒍𝒊𝒆.

Hollis puts it most precisely of all: "𝗧𝗵𝗲 𝘀𝗲𝗰𝗼𝗻𝗱 𝗵𝗮𝗹𝗳 𝗼𝗳 𝗹𝗶𝗳𝗲 𝗶𝘀 𝗮 𝗰𝗼𝗻𝘁𝗶𝗻𝘂𝗶𝗻𝗴 𝗱𝗶𝗮𝗹𝗲𝗰𝘁𝗶𝗰𝗮𝗹 𝗲𝗻𝗰𝗼𝘂𝗻𝘁𝗲𝗿 𝘄𝗶𝘁𝗵 𝗱𝗶𝘃𝗲𝗿𝗴𝗲𝗻𝘁 𝘁𝗿𝘂𝘁𝗵𝘀 𝘁𝗵𝗮𝘁 𝗮𝗿𝗲 𝗴𝗲𝗻𝗲𝗿𝗮𝗹𝗹𝘆 𝗾𝘂𝗶𝘁𝗲 𝗱𝗶𝗳𝗳𝗶𝗰𝘂𝗹𝘁 𝘁𝗼 𝗯𝗿𝗶𝗻𝗴 𝘁𝗼 𝗰𝗼𝗻𝘀𝗰𝗶𝗼𝘂𝘀𝗻𝗲𝘀𝘀 𝘂𝗻𝘁𝗶𝗹 𝘄𝗲 𝗮𝗿𝗲 𝗳𝗼𝗿𝗰𝗲𝗱 𝘁𝗼 𝗱𝗼 𝘀𝗼."

As I reflected on that passage, I began to recognize something.

The encounters had not started there. They had been accompanying me for years — perhaps decades — often unnoticed while I was busy living them.

Some arrived through people. Some through roles and responsibilities. Some through books, teachers, and traditions. Some through questions that refused to leave. Vertical development. Dialogue. Systems thinking. Embodiment. Presencing. Myth and meaning-making.

Looking back, I can now see them as a long trail of encounters, each one enlarging something, each one revealing something previously unseen.

And over time I began noticing a pattern. Some encounters left me essentially the same person. Others expanded what I could see, who I could become, and what felt possible.

I eventually began calling these Generative Encounters — not because they always transform us instantly, but because they generate new awareness, new choices, new meanings, and sometimes entirely new chapters of life.

Some unfolded in a moment. Others took years to reveal what they had set in motion.

The premises behind this idea are something I will explore gradually in future issues.

I am increasingly curious about the encounters that enlarge us — and the conditions under which they become possible.

A coaching conversation can be a generative encounter. So can a book, a movie, or even a single scene.

The trick, I think, is not simply to consume them. It is to 𝑎𝑙𝑙𝑜𝑤 𝑡ℎ𝑒𝑚 𝑡𝑜 𝑓𝑖𝑛𝑑 𝑦𝑜𝑢.

But there is something I have only understood slowly, and it is the heart of why I am writing this at all.

Some encounters could not have found me earlier. The book I needed at fifty would have meant little to me at thirty. The questions I can sit with now would have frightened me before I was ready. The morning was not a lie; it was part of the journey that brought me here. Certain encounters arrive only when we are finally able to be changed by them.

So, I will leave you with the question that started my own second half — offered now as yours, if it fits:

𝐋𝐨𝐨𝐤𝐢𝐧𝐠 𝐛𝐚𝐜𝐤, 𝐰𝐡𝐢𝐜𝐡 𝐞𝐧𝐜𝐨𝐮𝐧𝐭𝐞𝐫𝐬 𝐞𝐧𝐥𝐚𝐫𝐠𝐞𝐝 𝐲𝐨𝐮?

𝐀𝐧𝐝 𝐥𝐨𝐨𝐤𝐢𝐧𝐠 𝐚𝐡𝐞𝐚𝐝, 𝐰𝐡𝐚𝐭 𝐞𝐧𝐜𝐨𝐮𝐧𝐭𝐞𝐫𝐬 𝐦𝐢𝐠𝐡𝐭 𝐬𝐭𝐢𝐥𝐥 𝐛𝐞 𝐰𝐚𝐢𝐭𝐢𝐧𝐠 𝐭𝐨 𝐟𝐢𝐧𝐝 𝐲𝐨𝐮?