What do you think are signs someone has made it?

Their time is their own and they have no issues about housing, food or health costs.

for me I "retired" at 40, adopted a frugal lifestyle and reinvested my surplus from having that lifestyle and that compounded over the decades. I've changed lifestyles along the way (off grid small mud brick cottage in the forest, high rise condo on the beach, now a small house on acerage on the edge of a small town) . I'm now 60

i boomerang travel back to Australia (my base) which is a quiet place on edge of a small rural town, with clean air and lots of outdoor activities, for 4 months a year and travel SE Asia for 8-9 months. I would like to add Europe into the mix next year as well.