Millstone or millstone means a large stone that was used for grinding grain in a mill, used figuratively to mean a heavy burden--
When the water turns the wheel, the millstone turns and grinds the grain.
He sometimes felt that his responsibilities were a millstone around his neck.
Milestone or milestone means a marker or sign used to mark a highway or route, often used figuratively to mean a significant life event--
Turn left when you see the milestone marked "7".
His first solo was a milestone in his career.
Now that you know that, you can say--
"Buying a house should have been a milestone in his life, but instead the old place was a financial millstone, sinking him deeper in debt every day."
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