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I'm usually a night-before kind of packer. But I usually over-pack and over-prepare. I'll bring everything from sunscreen, to rain coats, extras of every piece of apparel, even extra toiletries when I can.
I go from being totally unprepared two days prior, to basically ready to go on a month-long trip for a week vacation, in less than 4 hours.
That is my wife.
We agreed a week in advance to pack a specific size luggage. I had my luggage packed a week in advance. The night before she finally packed and we had to check a extra bag.
We were going to another metropolitan city. 😭😭😭
Oh, you're me.
Oh, I almost never go far from a major metro. I can buy anything I forget, generally a replacement is less than 10 minutes by car at most, and usually less than 5 minutes walking.
There's just something satisfying about the SO going "darn, I forgot my brush/comb/usb charger/phone cable/toothbrush/whatever" and within seconds I produce one for them.
I don't usually travel by plane so checking bags isn't usually a concern.
In my case it's similar, but specifically I overpack work stuff (camera gear, mostly) thinking I'll be taking time during vacations to film personal things/try new techniques/update my website/plan future shoots/do marketing/etc etc etc. All the stuff I never have time to do while grinding away at home.
Sometimes on big road trips where we don't visit family, I manage to film some personal stuff (landscapes, etc), but right now we're on the annual family visits trip and feeling like fuck no am I not gonna bother haha. Then I spend the whole time complaining about why on earth I felt the need to bring this cumbersome stuff every time I'm packing the car...
Something about, having it being better than needing it?
IDK.
honestly as a photographer - i rarely regret not taking it, trying to capture the moment makes you miss it