I lost my father in my early twenties, and only years later did I realize how much I took him and the time we had completely for granted. I never asked him the questions I should have once I became an adult. It’s easy to assume our parents and elders will always be around…until they’re not. And then, again and again, you’ll think of one more thing you wish you could ask them.

Years later, my father’s older sister, Rosa, who lived to almost 102, became a priceless resource for me. I visited her often. She said I reminded her of my father, who was her best friend, but she also gave me something I desperately needed: answers.
Stories.
History.
The pieces of my dad’s life that I never thought to ask him directly.

Those painful lessons taught me something crucial: don’t leave the important questions unasked. Not with your parents. Not with your grandparents. Not with anyone you care about. Life has no obligation to give you another chance.

As I’m writing this, we’re entering the holiday season—a time when many of us gather with family members we may only see once a year— so I encourage you to do something bold and meaningful:

Record the people you love. On video. Now.

Years ago, I recorded a 90-minute video of Aunt Rosa, just asking her about her life and my father. I learned many things that I had never known. That recording is one of the most treasured things I possess.

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On the other hand, I deeply regret not recording a message from my dear friend, Madelyn, for her grandson to show to his future bride someday before his wedding. She passed before I got the chance. Imagine what a meaningful gift that would have been.

Today, we live in a world where everyone has a video camera in their pocket. It’s easier than ever to capture those stories and messages. And trust me, future generations will treasure them. And so will you.

I also believe in recording some of these yourself. Record messages, thoughts, guidance, things your loved ones may one day want or need to hear. None of us is here forever, and boldness means acting before regret sets in.

A Small Story About Ruth

A few days ago in Whole Foods, an elderly woman in front of me insisted I go ahead of her in line, as she was only buying a cup of coffee. After some playful back-and-forth, I agreed and then bought her coffee, to which she slyly replied, “I do this trick all the time!”

We both laughed, and later I sat with her for a few minutes while she drank it and asked her about her life.

Her name was Ruth. She had no family nearby. Some were gone; others lived far away.

For her, that short conversation mattered. For me, it was a reminder of a younger version of myself who was uncomfortable talking to older people. And of how far I’ve come.

This, too, is boldness: Taking a moment to connect with someone who might otherwise go overlooked.

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THIS WEEK'S SUPERBOLD EXERCISE:

If the opportunity appears—and it almost certainly will—spend a few minutes chatting with an elderly stranger.

It will brighten their day more than you know.

And it will strengthen your boldness muscle in a meaningful, human way.

And please… don’t stack regrets.
Ask the questions now.
Record the people you love.
Capture the stories before they disappear.



Your future self—and your family’s future generations—will thank you.

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