Hi Josh. This is a big question at this time of year, for sure. You put your finger on what makes this a headache for me, personally – I’m not necessarily the best at crunching the numbers across different discount scenarios to spot the best deal/timing.
So, my approach is to bypass the math component and ask myself: “Is this sale item something that I need to buy ANYWAY?”
– If I legitimately need the item AND it’s on sale, that’s a green light
– If I need the item but it’s not on sale (yet), I MAY delay till I find a better price
– If it’s on sale and I only casually wish I had that item (“would be nice…”), that’s a no go
It’s not always easy to abide by this rule but it helps keep me out of the “but it’s on sale” trap. I think, over time, I end up saving money by buying fewer things that I don’t really need.