Lots of us made progress to where we are at by several means:

0) look at other people's lists to see how they do it.

1) slowly aquiring new gear and/or changing how we do things. Often this meant carrying, carefully, appropriate gear for the conditions we are going to face, as opposed to carrying year round gear the summer.

2) in combination with 1), going through our packs mercilessly after each trip, and outside of emergency gear, giving the critical eye to anything that wasn't used on the trip.

Plus, I revisit constantly.
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Any fool can be uncomfortable...
My 3 season gear list
Winter list.
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