Before meeting wife Joanna, the former "Fixer Upper" star said he wasn't interested in starting a family.
"I dated girls whose goal in life was to get married and have kids," he told People. "They had it all planned out, but I was too selfish. It was about me and what I wanted to do, and I didn't have anything tying me down."
That all changed when Joanna entered the picture, though.
"Not itching to get married, not itching to have kids. And then when Jo and I met, it felt like there was this real transition," he said. "I matured and grew up. It just kind of clicked in my brain: 'This is going to work.'"
Today, Chip and Joanna are parents to Drake, 14, Ella, 12, Duke, 10, Emmie, 9, and Crew, 11 months. They've also gone on record saying they may not be finished expanding their brood.
And though the Magnolia moguls have created a large family, Chip, 44, said his parents were initially concerned he and Joanna would never be able to have the money needed to take care of their kids.
"When you're first having babies, especially when you have parents like Jo and I do, it was all about 'How are you going to afford these kids,'" said Chip.
"When we had our first baby, our parents said, 'Great!' But by the third they were having these interventions with us like, 'Are you sure you thought this through? How are you going to pay for college?'"
Chip also admitted he's not a perfect father. In fact, he's far from it.
"I've made every mistake in the book with Drake and Ella both," he said. "There's lots of stories of me leaving kids places I shouldn't have left them.
"I've forgotten birthdays. Afterward you're like, 'I'm the worst person.' But I'm a firm believer that it's the mistakes that make us who we are."
Chip, who recently celebrated his 16th wedding anniversary to Joanna, said marriage didn't come easy at first either.
"I had to make a lot of changes," he said. "I had to be a better person. But when I thought about the idea of being an 80-year-old man sitting on a rocking chair with my beautiful wife, and for she and I to have made it [that far], I got really excited."