Recently, an old friend emailed me for help with his family's financial woes. The confession that followed wasn't pretty, and included tales of student loans, car loans, unrestrained spending, and empty bank accounts. It was all bad news, which I found rather surprising considering their relatively high income. So, of course, I asked about their fixed expenses. What were they? We emailed back and forth for quite a while, and he gave a few more details of their situation. For example, their house payment was only around $900. Affordable. Car payments and student loans consumed around $450 each month. Not shocking. Then there were the expenses that everyone must contend with -- things like groceries, gas, school supplies, and insurance. It was all rather boring.Follow the money trail So, what was the problem? This is a couple who easily pulls in six figures and lives in an incredibly affordable part of the country. Their fixed expenses were relatively low, but they were constantly coming up short on funds. Why? Obviously, something was going on, but they couldn't put their finger on it. And neither could I. "You guys should track your spending," I suggested. "That's the only way to see what you're spending your extra money on." He agreed, and I said that I would check back with them in 30 days. So I waited, and waited, and waited. A month later, I emailed to see what they had discovered. "We gave up," he said. "It was too depressing." "Depressing?" I asked. "More depressing than being broke?" Apparently so. "The kids are always needing something," he said. "And we hate staying home on the weekends. We want to go out and have fun." "But you'll never know where your money is really going unless you track it," I said. "Maybe you can just start over at the beginning of the month."