Interesting concept and responses...
It's somewhat similar to the "Let go without food and eat only what we can hunt and gather" challenge.
The overall reasoning in both is you will learn something about yourself and become more confident and skilled in the process. These feel to me like rushing the process though.
The thing is, you could learn to make do without intentionally leaving anything behind. There's really very little difference between not taking it and not using it, but neither of those give you the real life experience you're looking for.
That said, I know for sure I could do just fine with these items in most conditions for one night:
Large SOL emergency blanket.
windproof jacket w/hood
2 cup stainless steel mug
I'd rig the SOL blanket as a tarp for shelter, make a fire with sticks, a stove with rocks, use the cup to boil water, eat a lot of one kind of food, whatever it was, find a rock to use as a knife and whittle a stick for a utensil and find another big stick to defend myself from bears and axe murderers.
Now, for real life experience what I do instead is forget or break stuff. That way I can learn and relearn those lessons without really planning it at all. This method gives you the advantage of surprise, which is really much more devastating emotionally, and therefore arguably a much better approach to learning how to deal with it.
For example, I forgot my sleeping pad on a recent trip. Not long before that I forgot my stove. Now I know I'd rather forget my stove than my sleeping pad, but you might not learn that if you made a list like the one above.
"You want to go where?"