October 3, 2024

While Dr. Jaykyri (Jay) Simpson, the executive director of Young Man With A Plan in Boston, Massachusetts, was reflecting on his youth with me, he dropped a phrase that caught my imagination: humble don’t stumble.

How did this come to be a meme for Jay, and why am I offering it to you today?

Jay grew up in a town just outside of Fort Worth, Texas, with loads of siblings, aunties and uncles, grand- and great-grandparents, and an abundance of cousins and friends.

Material comforts were few, challenges were real, but “we were rich in love.”

And rich in lessons, too, it turns out, that Jay carries to this day. The source of many of these lessons was—perhaps to no surprise—Jay’s grandmother, Mrs. Peggy Jay Scott.

Peggy Jay was the matriarch of Jay’s childhood years. When all the parents were out working, her door was always open to the neighborhood. Where Jay’s mom was very strict, Peggy Jay could afford a grandmother’s balance between discipline and heart. That helped the lessons go down!

From what I can tell, Jay was a firebrand kid. If there was one thing he hated, even from a young age, it was losing! And Peggy Jay had some things to say about that!

In second grade Jay was pretty darn pleased with himself when his relay team beat the team with the fastest kid in school. He came home with all his blue ribbons, bragging up a storm. Peggy Jay was not impressed. “If you’ve already won,” she admonished, “there’s no need to brag about it. Remember there will be times when you don’t!”

Fast forward two years. Jay’s fourth-grade basketball team lost a tournament, and Jay made very sure the whole school knew he was pretty mad about it. Peggy Jay was asked to come and bring him home. You can imagine there were some words she had to say about that, too!

Through these conversations with his grandmother, Jay began to understand that winning and losing is on a continuum. Sometimes you win. Sometimes you lose. That’s not what matters. How you handle it is what matters. The character you show is what matters. The respect you earn is what matters.

Jay added, "There’s no use winning or losing if the behavior you display makes you lose a bigger game." And this is how he came up with his meme: "humble don’t stumble."

Mind you, as a man now in his 30’s, Jay still hates losing! But he gets the bigger game now.

And that is the secret sauce of his success. Today he leads a mentoring program for high-school-aged boys. He draws on the legacy of Peggy Jay and his big southern family vibe to help boys know they are loved, SEEN, and able to choose their bigger game.

I offer this to you today with an invitation to reflect on moments when you may find yourself out of touch with graciousness, and grace. When you are too invested in being one-up or one-down. When you are gloating or griping.

Admit it! We all do it!

But like Jay, remember the biggest win is choosing to be humble, from which credibility and respect are the worthy fruits.

And thank you, Peggy Jay, his namesake, for teaching there isn't anything to trip over when we hold onto this truth!

Yours on the journey,

Martha

About the author 

Martha Hopewell

“A leader doesn’t get the message across; a leader IS the message!” I coach clients worldwide to embrace the opportunity AND the responsibility of this truth by building their credibility and skill to become remarkable change-makers. I look forward to helping you show up bigger and better for what you care about while taking good care of yourself, and nurturing communities of effort that are positive, productive, and rewarding for your organization and your team.

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