The first part is mental. Get comfortable with the idea of wearing the same clothes multiple times on a trip. Overpacking is reassuring - it's your own personal insurance policy against anything going wrong on your trip. At least that's how is feels. In reality, it's a ball bearing chained around your neck. The fact is, things will probably go wrong on your trip and this is okay. You can handle it!
I once packed about 9 outfits for a weekend trip to Chicago and wound up wearing 2. Meanwhile, I had to lug a giant backpack and a duffle bag around the airport and train into the city. It was absolutely miserable and so unnecessary.
Why did I do this? Because I didn't want to risk wanting any particular item and not having it. I wanted to make sure everything went perfectly and wound up screwing myself over instead. If you are an overpacker, I'm sure this has happened to you at least once, if not regularly. How many times have you returned from a trip, unpacked, and stared at the pile of belts, dresses and lotions that you never even glanced at on your trip?
(Sorry, that last line was woman-specific. Men - feel free to substitute in jock straps, porno mags... whatever items you tend to overpack.)
This is the hardest part. Once you can mentally acclimate to the idea and embrace the prospect of luggage freedom, then you're ready for the next step.
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