Candid Conversations Newsletter: When the Reflection Ripples

Have you ever gazed into the mirror and seen the years staring back at you?

During a recent video call with an old friend, something within me finally found context, if not language. We were catching up, letting the conversation drift across time, when a quiet realization surfaced. I have known them for a long time. In that exact moment, the years came alive. They added weight and texture to our relationship. Time took on shape and form.

I didn’t see smooth skin filled with elasticity and vigor. I didn’t see the boundless enthusiasm of youth, the excitement over a simple swim, or the joy of a freshly picked mango. Instead, I saw the passage of time itself.

It also reminded me of my own mortality. My hair has grayed. My recovery time after a 5K has lengthened. These are not complaints, just observations. Markers.

This week, I did something I hadn’t done in a while. I attended a networking event. A happy hour. The kind of thing I once enjoyed and actively looked forward to. A space meant to connect with new people and reconnect with familiar faces.

At first, I felt the tension. Part of it was being new to the room. Part of it was sensing the excitement buzzing around everyone else.

As the evening unfolded and night became the backdrop, I met Kate.

After the basic introductions, the conversation deepened quickly. She spoke about her work with genuine enthusiasm. Her eyes lit up as she described what she does and how long she has been doing it. She walked me through her journey with clarity and intention. The college she chose. Her major. Her professional degree. What she learned in her previous role. Why she stepped into her current one. Where she hopes to be in five years.

She was bright, articulate, intelligent, and grounded. She carried youth, tenacity, and a clear vision. The kind of person anyone would appreciate working with in any capacity.

Kate is thirty-one.

At that age, I was moving fast, convinced speed was the same as direction. Watching her speak so clearly about her path, I realized how much of my own thirties were spent learning to slow down.

Youth is Wasted on The Young 👦🏾

I saw my reflection in my conversation with Kate. Her focus. Her drive. I am older than Kate, and at her age, I was navigating life differently. I was surviving. Holding tightly to what I believed was virtuous at the time.

How was I supposed to know?

Like Kate, I had a clear vision. Climb the corporate ladder. Vice President was the marker. “I can hit VP in two years, then Executive Director in three or four,” I told myself, all while balancing personal life and the expectations that came with ambition. I spent my twenties chasing that vision, negotiating its demands.

Wisdom is Wasted on The Wise 👵🏾

On a night during Covid, I sat quietly. A familiar playlist hummed in the background. A glass of  bourbon rested in my hand. No urgency. No resistance. Just space. Just thought. Holding a vibe.

And it dawned on me.

What am I chasing?

I didn’t have language for it yet, but I had context. Years have a way of offering that.

For my thirtieth birthday, I gathered five of my closest friends and we drove for 17 hours straight, miles dissolving into laughter, arguments, music, and reflection, all to attend a men’s conference.

During the conference, a speaker posed a question that has stayed with me ever since.

You are born with a date. You die with another. Between them is a dash. What have you done with your dash?

Since that day, I have been defining and living mine.

Wisdom is Justified by Her Children🚸

That quiet evening, as I reflected on the chase, I finally understood what had been driving my questioning. I was chasing status. Relevance. The American Dream.

And then it struck me. The chase never ends. There is always something bigger. Shinier. More impressive. Offering more status.

I wanted to stop chasing and start living.

To live consciously. To move how I want to move. To choose how, and with whom, I spend my time. And for the moments I must be somewhere I would rather not, to remain calm while maintaining presence.

Now I see life as a greenfield. Full of unknowns. Known unknowns. Unknown unknowns. And I have drawn my line in the sand.

I can appreciate Kate’s ambition, her enthusiasm, her youth. I can offer perspective when asked. Be available when needed. I can honor the beauty of changing seasons and the quiet passing of time without regret.

Nothing is Wasted 🚮

That same evening I met Kate, I also met Sophia. She was fifteen years from retirement and aiming to be done in nine or ten, at most. I joked that she could shorten the timeline if she was willing to move.

Her eyes sparked, as if she was genuinely considering it.

“That’s an idea,” she said.

And just like that, I found myself between Kate and Sophia. Different perspectives. Different drives. One carrying youth. The other experience.

And in both of them, I saw myself.

There’s absolutely nothing wrong with that.

If anything, it confirms I was exactly where I needed to be.

The Ripples of Time ⌛

As time moves forward and space continues to stretch, one truth becomes clearer. Wisdom does not rush. It arrives through discernment. Through the eyes, ears, heart, and mind shaped by lived experience. Over time, those faculties learn when to converge, and when to answer the call.

It brings me back to a line I’ve carried for years, one that continues to age with me:

A society thrives when old men plant trees whose shade they know they will never sit in.

At the end of that conference I attended for my thirtieth birthday, each of us was given a small packet of seeds. We were charged with a simple task: sow them. It was both symbolic and profound. A reminder that growth is patient, intentional, and rarely immediate.

As the night came to a close and I said my goodbyes, I reminded Kate of a few books I thought she should read. Nothing more. Nothing forced.

And if that is the only thing she remembers from our conversation, then I did what I was meant to do.

I planted a seed.

And that, I’ve learned, is enough.

Until next time…