I always pack an extra day’s worth of clothes. Two if it is a longer trip than usual. It has ended up being invaluable. Most of the time you never need that extra set of clothes, but when you do, it is a godsend.
I have had a couple delayed flights, and have traveled during bad road conditions. Having the extra set of clean clothes made the circumstances much more bearable. Being flexible is so important when you travel. If it is a long delay, you have some fresh clothes to change into while you continue to wait. I prefer waiting until after the flight and slipping on something fresh to hit the ground running. Instead of being too put out by unforeseen circumstances, I have a little buffer to make the added stress more bearable.
I also always pack in extra day or two of pills. It is better to have them with me and not need them, than to not have them at all. Personally, I hate traveling with a whole pill bottle because I am so nervous they will get lost. I take what I will need with some extras. A real lifesaver sometimes. Once I missed putting a pill in a couple of the day slots, but I had the extras to replace them. Super handy that time!
If you use daily contacts, always pack a couple of extras. A couple of times I had some contact issues while traveling and the extras really saved me. I travel to see new places, so without them I would have had to rely on my glasses which are not as great as the contacts for sharpness even though they are both current prescriptions. Once I left my glasses at home on accident so the extra lenses were very valuable that trip in case of a mishap.
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