Raising “Haves” When You Grew Up a “Have-Not”

The Connecticut Post recently ran a story about the two Connecticuts—the one of yachts and private schools and the one of food insecurity and paycheck-to-paycheck living. It hit a nerve. Not because it was surprising but because it was so familiar.

I grew up in the latter Connecticut.

My childhood was filled with love but not with money. We lived below the poverty line in my grandparents’ house. There were a lot of “nos” in those years. No Pop Warner cheerleading. No ice cream at school lunch. No tanning sessions in high school (yes, it was the early 2000s—we were all making bad skin choices back then). It always felt like the other side—the “yes” side—was where life happened—the side with green lawns and air conditioning and actual vacations.

When I got a scholarship to a private middle school, I stepped into that other world. Let me tell you—it was a culture shock. Suddenly, I was surrounded by kids whose parents drove luxury cars, went skiing every winter, and didn’t blink at the idea of buying a $90 hoodie from Abercrombie. Meanwhile, I was silently praying no one would notice my $9 jeans from Bradlees.

By the time I graduated high school, I was desperate to get out. Most of my classmates stayed. A lot became parents within a year of graduation. Some are grandparents now. At 42, I’m still packing lunchboxes and reminding my kids to wash behind their ears—I cannot imagine being someone’s grandma right now.

I left Connecticut for college, thinking I’d never look back. Then 9/11 happened. Like so many of us, I felt shaken and scared. I knew people deployed overseas. I came home, transferred to a local school, and kept a wide berth from my hometown. I needed distance. I needed air.

Eventually, I attended graduate school thousands of miles away. Nobody knew me there, and when people assumed I was from the “rich” Connecticut—the one with the sailboats and prep schools—I didn’t correct them. It felt like freedom.

For once, I didn’t have to explain the free lunch forms, why I never went to summer camp unless a campership paid my way, or why my mom sometimes worked more than one job, and we still came up short.

Fast forward to today, and life looks very different. My husband and I are both professionals. We live in a good school district. Our kids are involved in activities, and they never have to worry about crossing their fingers and hoping we can swing it financially. They don’t flinch when we say “yes” to extras—really expensive dance costumes, dinners out (sometimes more than once a week), and birthday parties at trampoline parks.

We are firmly in the “haves.” And that’s weird. Beautiful, yes. It’s a blessing, definitely. Because I remember what it felt like to be on the other side. I still carry that version of me around—the girl with the generic cereal and the free lunch ticket tucked in her backpack. And now I’m raising kids who have no idea what that life looks like.

So I try—really try—to make sure they see it. That they understand not everyone lives the way we do. We talk about giving back. We talk about gratitude. And when my daughter leaves food on her plate because she “wasn’t in the mood for apples today,” I pause. Not to shame her. But to help her understand that a fridge full of options is not a universal truth—it’s a gift.

I want them to grow up knowing they’re lucky—but not entitled. Comfortable—but not blind.

Parenting is hard enough without the emotional math of our own childhoods creeping in. But for those of us raising “haves” after growing up as “have-nots,” it’s always in the background. The push to give them more while also trying not to raise kids who expect more. The joy of giving them everything you didn’t have—and the fear that you’re erasing the grit that made you who you are.