"I Want To Retire Early But I'm $44,000 In Debt"

Trina, 38, called into The Ramsey Show with a clear ambition: she wanted to retire by 40, just like her father had done twice. Her dad retired from the city and then from semi-professional boxing, both before turning 40, and that inspired her to set the same goal. But when the hosts asked about her current financial situation, the gap between the dream and reality became stark.

Trina makes about $60,000 a year and carries $44,000 in debt: roughly $20,000 on a car, $16,000 in credit cards, $4,000 in personal loans, and $2,000 owed to her son's private school. She had filed for Chapter 7 bankruptcy two years earlier. The bankruptcy was triggered when she tried to start her own government-contracting company, only to have the government agency pull all her existing clients. She went from a decent income to nothing overnight. While waiting for the new business to generate clients — it took about a year and a half — she drained her children's college funds, pulled from retirement, and took on debt. She also filed an adversary proceeding to discharge student loans through the bankruptcy.