Wit, Wisdom, and the Sensei of Surprises: Dad’s Masterclass

People often ask me, “What was your dad like?” In part, because my mom’s personality is so vibrant, they wonder who could possibly be the yin to her yang. There’s genuine curiosity, too, because I never talk about him in any concrete tense. I know they wonder: Is he alive? Is he still...around?

All of the above.

Today, however, he would have turned 67. So, I’m feeling moved to share one of his go-bys, his philosophies, if you will.

How good of a scholar I was growing up is debatable. But cunning? Always. Given Pops was a scientist, he certainly knew this. He was the kind of person who would adjust his methods based on the situation to achieve his goal. When it came to talking to my Uncle Bill, he took a cerebral approach. With my mom? A team-based, “we’re in this together” Socratic approach.

For me? I’ve always been a bit… unconventional. Part rebel, part logic warrior. So, his approach to me was largely aimed at finding the right question to neutralize my cunning nature. 90 percent of the time, he chose to mislead me at the beginning of the conversation to get my guard down, followed by his true intention. He loved this game. How off-guard could he catch me? “Got to keep you guessing,” he’d insist. “Can’t believe I caught you slipping,” he’d remark.

He found joy in asking the right questions. And it wasn’t just about being clever. It was about making me think—about pushing me to figure out the answer on my own rather than handing it to me. Looking back, I realize how much that influenced how I approach problems today. I’m always trying to find the right question to ask, whether at work or in life, because I learned early that the right question could unlock the best answer.

While I was a junior at Howard, before we started missing him, he used to text me. To this day, I don’t know why he rarely called. Maybe he figured I should either be in class or on a date. But the texts? I still have most of them. He’d repeat himself. Because, you know me, I’m a little “hardheaded,” as my Uncle Henry would say. After all, I am also a Winder.

Today, one of those messages springs to mind. It went like this:

“Fight the temptation to do anything but study. Nothing is more important than studying—not meetings, not Facebook, not friends, only your work. You must succeed… you are allowed to exercise, though.”

By this point, my eyes were well into the back of my head.

He continued, “I have one question for you… What is the temperature in the library where you are….‘dude’?”

Now, I thought this was odd! Hahaha. Dude? Temperature? The old man led with his standard “you need to x, y, z,” then instead of saying for the 67th time that I should be in the library studying every day, falling in love with every subject, he asks a question implying that I could not possibly be stupid enough to not be in the library. He wanted to verify by asking a question that implied I’d listened. This tickled me. I think he even used an emoji. Very on-brand.

It was almost as if, just when I’d start to roll my eyes, he’d hit me with a bit of unexpected cleverness. To be clear, y'all, I always knew it was coming, but NEVER when. It was his way of getting through to me without hammering it home too hard. He always kept me on my toes. That was my dad. Thoughtful, strategic, clever.

Another memory that sticks with me is how he’d always find a way to mislead me just enough to make me think. Like the time he asked me, “What’s the most important tool in a toolbox?” My mind immediately raced to answers—hammer, wrench, screwdriver. No, hmmm, ruler! He let me fumble about before smirking and saying, “The most important tool is the one you need.” I failed to think “beyond my nose” ...again. I still laugh now at how Ludacris his assessments were. This isn't even an exam bro. "It's always an exam."

I'm still laughing to myself.

Here’s to you, Dad—on what would have been your 67th birthday. Thank you for keeping me guessing and for always finding ways to make me think a little differently, laugh a little louder, and stay… dangerous.

I still carry this.

I think a lot about how to ask the right questions. How to keep people guessing just enough to make them think—and maybe laugh. How to approach challenges with a bit of strategy and cleverness— like him.

The truth is, even though my dad’s not here, his lessons still guide me. Whether it’s in a tough moment at work, a conversation with friends, or just making decisions in life. He lives in my psyche. Always looking on with slight disapproval, yet, slightly impressed. Reminding me to think just a little bit deeper. Imploring me to consider the nuance.

“Memento Mori.”

And maybe that’s his last lesson: to live with purpose, curiosity, and a sense of humor—because none of us get out alive. And he was right, we do miss him now that he is gone.