Derek Sall, 31, still remembers the first time he realized he was in debt — and the spike of motivation he felt to pay it off.
Sall's then-wife had returned to their house from the mailbox carrying their first student loan bill. It caught the young couple completely off guard.
"I think that happens to so many people: It's six months after you graduate, you're not thinking about it," Sall explains to CNBC. "I was sitting at the computer, doing our budget, realizing we were going backwards already."
From there, Sall, who chronicles his financial journey on his blog, Life and My Finances, resolved to get out of debt as quickly as possible. Between his wife's $12,000 in student loans, his own $6,000 worth of loans, and some outstanding credit card payments, the couple carried about $20,000 worth of debt between them.
They began aggressively attacking it, and managed to pay everything back in full within 14 months.
A few years later, Sall, then 27, found himself underwater again.
He and his wife had divorced, splitting their assets down the middle. Because Sall wanted to keep the house, he ended up owing his ex $21,000. He also had $60,000 left on their $75,000 mortgage to pay.