Nearly 40% of parents expect to take on debt to cover back-to-school costs this year. 15% say they have used personal or payday loans, and 8% admit they have gambled to pay for school supplies. Beyond Finance calls this the “Back-to-School Parent Trap”: the tug-of-war between protecting a family’s finances and making sure a child does not feel different from their classmates. “Parents aren’t just buying school supplies. Take Advantage of Tax-Free WeekendsMany states hold sales-tax holidays for school supplies and clothing, usually in the weeks leading up to the new school year.