Life Through the Eyes of an 8-Year-Old: Insightful and Funny Reactions (Lenny the Kid)

This one is one of my favorites because it’s not a guest, not a city, not a “how-to”… it’s just me sitting down with my kid and letting him run the show.

He kicks it off by introducing himself like he’s on a late-night talk show — first name, last name, full confidence — and immediately I’m realizing I’m not interviewing my son… I’m being interviewed by him. And he comes in hot with the real questions: When do you become “old”? What age does “grandpa” start? And apparently, according to my eight-year-old, I officially crossed into old-man territory at 38.

That part was brutal. But also hilarious. One year ago I was safe. Today? Grandpa Dad.

From there, the conversation turns into a surprisingly honest little window into how kids see the world. We talk about whether it’s more fun being a kid or an adult, and he doesn’t hesitate: being a kid wins. His reasoning is flawless: adults have to “walk every single day of the year” (translation: go to work), and kids don’t. He also has a better grasp on why adults work than most adults do — because you have to make money for your kids… and also because kids are expensive. Food, water, shelter… and, of course, Jordan 1s.

Yes, my son is already budgeting for sneakers.

We get into the economics of childhood too. He starts throwing out numbers for what people make and what houses cost, and none of it adds up — which honestly feels like an accurate reflection of the economy anyway. At one point “regular people” make $50 an hour but somehow also only make $5,000 a year, and houses cost a million dollars unless it’s a “cheap house.” It’s chaos, but it’s pure, and it’s hilarious. And it also reveals something real: kids are constantly trying to understand money, work, and “how life works,” even when they don’t have the math yet.

We also hit the big milestone question: what age should a kid get a phone? His answer: nine. Which means I have about one year left before I get that negotiation packet slid across the table.

But the best part of this episode is the vibe. It’s funny, it’s playful, and it’s one of those conversations that starts as a joke and ends with something you don’t forget. Right at the end, out of nowhere, he drops it on me:

“You’re my best friend.”

And that’s it. That’s the whole point.

If you’re a parent, you’ll get it. If you’re not, you’ll still probably laugh. Either way, this episode is a reminder that the stuff we think is “small” is actually the stuff that matters.