His actions caught up with him. He was unable to maintain the house where he lived and moved in with his sister to save money.
"It's a very personal thing, finances. It's like religion. It's like sex. It's hard to kind of really disclose everything about it," he says. "At this point, I had such pain. I had to alleviate that pain."
He talked to a credit counselor, who helped him budget and get a handle on his finances.
His debts, including credit cards, a student loan and a car loan, at the time amounted to $55,000. Through debt management, he took aim at his $6,229 in credit card debt and has whittled it down to $4,086. He says he's paid off more than one-third of his other debt.
He also enrolled in Weight Watchers and has shed 85 pounds.
It hasn't always been easy. He slipped up once when he didn't have enough to pay a card issuer. Hamilton has since worked out a payment plan with the creditor and is building a savings cushion so he won't have a shortfall again.
Early on, he says, the hardest part was giving up credit cards. Today, he sticks to a debit card.
For her part, Clay-Boone was happy to give up her plastic as part of her debt-management plan.
"I really didn't want to use the credit cards," she says. "I had that much debt."
Debts started piling up when she took on the bulk of household expenses as her marriage faltered several years ago, says Clay-Boone, 60. She worked 30 years with Verizon before taking a buyout in 2001, after which she held a variety of jobs.
Eventually, her card payments became too much to handle. "I was a little overwhelmed," she says.
She tried unsuccessfully to negotiate with creditors on her own before enrolling in debt management in October 2009. By then, her balance totaled $68,810 on about a dozen cards, one with a rate of 27 percent.
A counselor was able to get Clay-Boone's interest rates into the single digits. She now pays $1,263 a month under the debt plan and has worked off more than $28,000.
She has faced numerous challenges. The most serious: She was laid off last April from her customer service job at a Verizon subsidiary.
But she got some help. Several months ago, she qualified for a federally funded loan program designed to help homeowners who suffer temporary setbacks. It pays about 70 percent of monthly mortgage payments, for up to two years. If the homeowner continues to keep up with the payments thereafter, the federal loan is eventually forgiven.
Clay-Boone says her monthly income from an annuity and unemployment benefits is $3,120. She says that she doesn't have much left after paying her bills, and that an emergency could wipe out that cushion. She hopes to start job training this month so she can work as a medical assistant in a hospital.
"I am definitely not a person to give up," she says.
As the experiences of Hamilton and Clay-Boone illustrate, it's hard work to begin the process of eliminating debt. But it can be done.
"The first few months are actually the hardest," says Lynnette Khalfani-Cox, a money coach and author of "Zero Debt: The Ultimate Guide to Financial Freedom." She speaks from experience, having racked up $100,000 in credit card debt — which she paid off in three years.
She advises consumers digging out of debt to start by writing down all outstanding bills. Many people don't even know how much they owe, she says.
Look for expenses to cut. This might call for some tough choices. Khalfani-Cox, for instance, moved her children out of their pricey private school to a less expensive one.
Find ways to do things for free or cheaply. Khalfani-Cox goes to the library instead of buying books.
Negotiate with creditors to get better terms, she says.
And if you need help, check out a reputable nonprofit credit counseling agency.