I routinely travel with a single small bag and disagree with the primary claim of this site: that a packing list is needed to travel light. Sure, it is useful in other ways such as not forgetting things. But to me packing light is as easy as not bringing things I don’t need. You could just ask yourself if you really need something every time you pack it. If this question wouldn’t work, I can’t see how applying the same logic in list form would perform any better.
If you are anxious about traveling, then you are likely to over prepare for every scenario you think you might encounter. It is difficult for someone in this situation to do what you suggest because the asking whether something is really needed will result in "yes" because it is there to solve a situation they have anxiety about.
Without a coping mechanism for the anxiety, it is difficult to change the packing behavior. Having a friend review items with you is going to be much more effective because they can have that back and forth about whether the situation is likely or not. This situation is something people discover with their partners when they travel for the first time. Initially, it is tolerated, but as the relationship progresses it becomes more of a challenge either through travel constraints, or requirements for joint packing.
If you are anxious about traveling, then you are likely to over prepare for every scenario you think you might encounter.
That was the conclusion I came to on a motorcycle trip to Prudhoe Bay, Alaska, which travels down the 400-some miles of the gravel haul road. Everything I had, and everything I needed, fit within the two saddlebags, the duffel strapped to where the passenger seat used to be, or the tank bag. No shit bungied to seat backs and saddlebags, just a nice, clean look. Were I out for two weeks or two years, didn't matter, I could live off that bike indefinitely with what I had.
And then there were the Jed Clampetts[0] of the motorcycle world, with stuff strapped everywhere, and little bags strapped to the frame, spare tires hanging off the back. I saw more of those than I did those that IMO did a more reasonable job of packing. Having spoken with a few around the campfire, my experience says that the hard-core experienced riders pack about like I do (editor's note: mikestew is NOT a hard-core rider, though he is experienced). Newer folk don't know they're not going to need it on that 2 year old BMW, so they pack it just in case the ABS module does go out.
I think life experience is a factor, though I'm a bit scant on anecdata for that one. Ever go backpacking? More than once? You might be a light packer. Most adventurous thing you've ever done is stay in a Motel 6 instead of a resort hotel? You might be attached to those two carryons and 125 litre checked bag.
In conclusion, yeah, "just pack less" doesn't work for a lot of folks. That might change later, or it might not. But in the meantime, a checklist constructed in conjunction with another traveller can set the constraints necessary to keep the imagination running wild with what might be needed.
If you travel a lot, it can also work to have one or two small pre-packed kits that contain various electronics, repair items, OTC medications, earbuds, etc. I'll adjust my electronics kit some--like I'll take out my presentation clicker if I'm not presenting. But basically I have a travel pile and I mostly just grab some things from that pile and toss them in my bag.
