From Gutters to Kindergarten: What I’d Tell My Future Self

41 Hits Different

They say age is just a number. But let me tell you—41 is a very different number than 21.

At 21, I bought two 12s for the car, bragged to my friends, and stayed up until 2am.

At 41, I bought gutters with leaf guards, bragged to my neighbors, and was in bed by 10pm.

Funny how the things we brag about change. At 21, I had no idea what life at 41 would really look like—yet here I am, gutters and all.

And today? Today is my 41st birthday… and my daughter’s very first day of kindergarten.

One of us thought about faking a fever to get out of going. The other one wore a backpack and ran into the classroom with big smiles.

She is definitely braver than me.

Which makes me wonder… if I was that clueless at 21 about what 41 would bring, what’s 61 going to be like?

Let’s send him a letter, just in case.

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Dear 61-Year-Old Me,

You better not have uploaded your consciousness into a robot. I don’t care if it can run a go route without spraining an ankle—or switch shows on Netflix by simply blinking your left eye. We’ve always believed in change, remember? That includes you embracing those old knees and that stubborn back pain.

Still, I hope the things you value haven’t changed much. I hope you’re still bragging about the little things—maybe it’s a new grill, a bigger TV for football Sunday, or finally beating the kids at ping pong and darts.

Don’t take it easy on them. They’re old now…

I hope the gutters you bought at 41 are still holding strong (and if they’re not, I hope you got the senior discount on replacements).

I hope Mom and Dad are doing well. I hope they truly understand how much they meant to this version of you—their sacrifices, lessons, and love woven into every part of the man you became.

I hope the family is thriving—your kids building lives they love, and your wife still putting up with your next big creative idea. (Are you really running for office, or was that just a joke?)

I hope you created real change in the child welfare space like you always wanted. The only reason you wouldn’t have is if you gave up trying—and I know you wouldn’t do that.

I hope you published those next three books. They’re already done, so they better be—especially that one you know is going to be a game changer.

I hope you’re still inspiring people. Who knows what the world looks like in 20 years, but remember: the only things that separate you are the lessons you learn and the chances you take.

I hope Maggie and Frankie are following their dreams, too. Do they know how proud their mom and dad are of them today?

If life at 41 taught you stability, it also taught you patience, unconditional love, and the humbling truth that no matter how much you think you know, there’s always more—deeper, harder, and richer things to learn than you can possibly imagine right now.

I do hope 61 is teaching you gratitude—that quiet kind that sinks into your bones when you realize the loudest parts of life are behind you, and the richest parts are right in front of you.

Keep showing up. Keep loving well. Because one day, you’ll realize the loudest brag you have is the legacy you’ve quietly built—and the people who are living it with you.

And if I've learned anything, it's that what you’re proud of at 61 will outshine anything I could have imagined today.

See you then, Curtis

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Disclaimer

If you are reading this, the views expressed in this blog are solely those of the author and do not represent any other individual, organization, or company. This content is intended for general knowledge and to highlight tools, techniques, and ideas that inspire positive change. Readers are encouraged to explore the topics further and form their own conclusions.

If 61-year-old Curtis is reading this—first of all, wow. That means Google still exists… and so does Speak4MC. Hopefully you’ve added some new trainings by now.