Candid Conversations Newsletter: The Dichotomy of History

There is something about long friendships. They hold memories without needing explanation.

Recently, I sat with a couple of friends I have known for a long time. We spoke about discipline. About focus. About the subtle nuances that are not readily visible, yet often costly when ignored. We spoke about mentorship and how access to the right guidance might have altered the trajectory of our lives. Hindsight is always clear, they say.

I have often said that if I changed even one thing in my past, it would alter my entire life’s course. That is the paradox. We long to adjust certain chapters, yet we also understand that every page shaped who we became.

Mentorship matters. We cannot deny that. So does proximity.

I did not have a formal mentor early in my career. But I had examples. I had proximity. I had people around me who were doing things I wanted to be involved in.

Take Micky.

I met him early in my professional journey. He was smooth, charismatic, dressed with intention. Super 120 wool blend suits. Double vented. Two-button notched lapel. Tapered sides. Some days he wore a double-breasted peak lapel. Pinstripes. Herringbone. The details mattered.

But it was not the suit that stayed with me. It was how his eyes lit up when he was with a client. The way his love for the work revealed itself in conversation. The precision. The composure. The presence.

He may not have known it, but he was mentoring me by example.

That is one side of the dichotomy. The absence of structure, yet the presence of influence.

Those Who Planted Trees 🌱

I have always been drawn to the 1970s. It felt like one of the most progressive and socially charged decades in modern history. Across the Caribbean and Africa, nations were defining identity, shaping sovereignty, building futures independent of colonial conditioning. There was a sense of camaraderie among emerging states, a shared hunger for self-definition.

I sometimes envy those who grew up in that era. It must have felt like standing at the edge of possibility.

I recently watched an interview with Maurice Bishop, the Prime Minister of Grenada who was later assassinated in 1983. Bishop was instrumental in shaping Grenada’s direction after the 1979 revolution removed corrupt leadership. He spoke with conviction about national pride, sovereignty, and the psychological work required to break free from a colonial past.

His story is layered. Vision and vulnerability. Momentum and fragility. Nation-building and political fracture.

Another dichotomy.

We often romanticize eras. Yet those same eras carried turbulence. Progress and peril lived side by side.

The Past ⌛

In risk management, inherent risk is the level of risk present before controls are applied. It is raw exposure.

Our past is similar.

Our inheritance, cultural memory, subconscious patterns, family narratives. They are inherent. They exist before we consciously apply “controls” in the form of discipline, therapy, mentorship, reflection, or faith.

Bishop’s legacy remains a reminder of how quickly systems can shift. How fragile progress can be. How power can consolidate or collapse.

But there is strength in this understanding.

The past shapes us. But it does not own us.

There is power in our past. Not because it confines us, but because it informs us. The stories we inherit are not instructions. They are data points.

The dichotomy is this:

We are shaped by what came before us.

And we are responsible for what comes after us.

Mentorship matters. History matters. Proximity matters.

But so does authorship.

And perhaps maturity is learning to honor the past without being imprisoned by it.

The Past As Our Mentor 🕴🏽

All my passions, the disciplines I’ve cultivated, the questions I wrestle with, have been shaped by those who came before me.

The past is brutal in and of itself. War. Ethnic cleansing. Systems built on exploitation. Atrocities committed in the name of power, profit, or preservation. And yet, within that same past, we find beauty. Resistance. The fight for equality, peace, justice. Liberation.

Both are true.

I was never one who fully embraced the idea of Black History Month. I used to ask, why do Black people need a month to remember their past? Should history not be whole? Integrated? Continuous?

But this month finds me more curious than ever about the juxtaposition of Blackness and history. Not as a compartment, but as a lens. A magnifying glass that forces remembrance.

A Past Awakens 🧬

I have always loved long drives.

From one end of the island to the other, through hills and valleys alike. That love followed me to the United States, where I now find myself driving across state lines, often choosing the scenic route over the efficient one. There is something meditative about it. Something grounding.

Part of my dream is to drive the East Coast of the United States, then along the Gulf Coast, through the Northwest, and across the heartland, visiting national parks along the way. Romantic in thought and in theory, after all, this is a beautiful country.

But sometimes, while driving, I am jolted by a sudden consciousness.

Just decades ago, I would have needed to be careful not to end up in a sundown town. I would have needed the Green Book in my glove compartment to know where I could safely stop for food or lodging.

The reality of the segregated South under Jim Crow was not ancient history. It is within living memory.

The Negro Motorist Green Book existed because safety was not assumed. It had to be researched. Curated. Verified.

Jim Crow laws enforced racial segregation in America well into the twentieth century.

And across the Atlantic, Apartheid institutionalized a rigid separation that denied Black South Africans citizenship, restricted movement, dictated work, and stripped away fundamental rights until 1994.

These were not misunderstandings. They were systems.

America had Jim Crow. South Africa had Apartheid. Different geographies. Similar logic.

When I drive freely today, that freedom sits on the shoulders of people who did not have it.

That is what Black History Month is beginning to mean to me.

It is not about isolation. It is about intentional remembrance.

It is a pause. A deliberate act of sitting with the fullness of what was. Not only the pain, but the courage. Not only the brutality, but the brilliance.

Remembrance is mentorship.

To study those who endured and overcame is to sit at their feet. To glean wisdom from their restraint, their resistance, their strategy, their faith. It is authorship by inheritance.

The past mentors us, even when we resist the lesson.

And perhaps the greater dichotomy is this:

The same species capable of designing systems of oppression is capable of dismantling them.

What man has done, man can do.

If injustice was engineered, justice can be engineered.

If separation was codified, dignity can be codified.

The past is not simply a record. It is a curriculum filled with data points.

And whether we choose to learn from it may determine the trajectory of what comes next.

To ignore it is to risk repeating it. To study it is to build differently.