just found a name for the store: Dress And Go,” Jaden Weems announces, as he describes his latest entrepreneurial concept, in which customers would go online to design anything from sweatsuits to formal wear, made-to-order.

“Instead of having it made in China and delivering it, it'll be made in that store,” he says. “As soon as you order it, we'll be like, ‘OK, we'll have it prompt in like three or four hours.’”

Mr. Weems loves his son’s ambition and his daughter’s drive to study at the Massachusetts Institute of Technology. Sometimes, though, he worries that his kids, both of whom take advanced courses at Woodland Hills, occupy an uneasy bridge between two worlds. “We've got Forest Hills on one end and Rankin on the other end. And we're in the middle. And you can’t really be both. But I want them to be both.”

He can feel the tension between Rankin’s inertia and his efforts to improve his family’s situation. Push too hard? “You become the smart-ass. You become the know-it-all.” That can blow back on the kids.

So as he mulls expanding the family home, putting in a dormer and a deck, a new kitchen and a larger bathroom, he has to think about how that will be viewed. “That's something that doesn't really happen around here, so you've got to be careful,” he says. A big, visible home improvement can cause “issues [for the kids] at school. ‘Oh, ya’all think ya’all got money.’”

He looks out his front window, to the empty lots across the street that wait for the wave to come up from the furnace site below. That urge to invest in “the best city” surfaces again.

“We could buy that space and build there,” he muses. “But do we want to spend the rest of our lives in Rankin? I don’t know.”