What My Grandmother Taught Me About Legacy

Two years ago, in a packed church, I learned more about legacy than any class or book could have taught me.

I was at my grandmother’s funeral. She lived to be 92. In addition to raising six children, she started a record shop in her hometown of Detroit in 1966 and ran it until 2019.

Simpson’s Records became more than just a place to buy music. Over time, it added penny candy, hot food, and even a few arcade games. As the neighborhood changed, her store stayed the same. It became a constant. She offered jobs to local kids, handed out coats and meals to those in need, and gave out the kind of grandma hugs you still feel years later.

She wasn’t just the matriarch of our family. She was the matriarch of the neighborhood.

Her funeral was standing-room only. No speakers mentioned her title. No one mentioned that she was one of the only Black women running a business in Detroit in the ’60s. No one mentioned how much revenue the store brought in.

Every single person talked about how “Ma Simpson” made them feel.

That moment stuck with me.

It made me ask: What would people say about me if I left my job tomorrow?

At some point, we’ll each leave our jobs. We’ll leave behind projects and results. But long after those fade, what sticks is how we made people feel.

Maybe today you’re tired. Maybe someone at work is getting under your skin. It’s fine to feel that. But how you consistently show up shapes what people remember. That’s your legacy.

At the funeral, one of my uncles told a story. He was working at Simpson’s when a group of kids came in with 25 cents each. They agonized over what candy to buy. They picked something, changed their minds, picked again. My uncle got frustrated. Then my grandmother stepped in and said:

“Honey, look. They got a little bit of money and all this candy. It’s a major decision. Don’t you ever rush them.”

She could’ve let it slide. But she didn’t. She saw a teaching moment. She showed patience, respect, and care. Even though it was small, that’s what people remembered about her.

So, what story do you hope someone says about you at your goodbye party?

Here’s what I’d want to hear:

• He always had my best interests in mind

• He listened, even if he didn’t have time

• He told me the truth and helped me see things I was missing about myself

• He wanted the best for me, no matter what

I’m not there yet. I’ve missed moments to speak up and avoided hard truths to keep the peace. But knowing how I want to be remembered helps me course-correct.

You can do the same:

1. Choose 2–3 things you want to be known for

2. Write them down somewhere visible (on your desk or wherever you take notes)

3. At the end of each day or week, ask yourself: Did I act in line with those values?

Titles come and go. But how you make people feel leaves a mark. And it’s fully within your control.

Start small. Help people feel. Live out your legacy. Don’t wait until it’s too late.

Until Next Time,

Winston