Unpopular opinion: paying off your smallest debt first is a trap, and my coworker's math changed my mind
Last month my coworker Dan and I were grabbing lunch at a sandwich place near our office in Cleveland, and he said something that stuck with me. He told me he paid off a $1,200 credit card first instead of his $8,000 one even though the big one had higher interest, just because the small win kept him going. I always thought the math people were right and you should always hit the highest rate first. But Dan said he tried that for 2 years and kept quitting because it felt like nothing was happening. He cleared the small card in 4 months and used that momentum to knock out the big one in a year and a half. So now I am stuck between two sides: pure math says highest interest first, but real life says whatever keeps you actually paying. Which one has worked better for you, the math way or the feelings way?