I seem to always either overpack or under pack when I'm going on trips; what are some packing strategies that can help me avoid this problem?

Pack for the amount of days you will be gone for. This includes socks and underwear. Next, pack pieces of clothing that are interchangeable. So, instead of packing 7 shirts and 7 pants, only pack 3 pants and 4 shirts.
Be realistic about what you are going to wear. A lot of people will save outfits for when they travel, but never end up wearing them.
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