I am about nine years from retirement, unless health concerns force me to go sooner (not impossible by any stretch of the imagination). The cost of living where I live now (Vancouver), likely will make retiring here unaffordable. My goal when that day comes is for everything I own to fit into two suitcases, and winter in Southern Europe (Spain/Italy/Greece) There is work to be done.
Obviously, I have got some time, but I have started the process:
1. I have hundreds of books. I have switched to an ereader and have started giving my existing books away, so I haven't bought a new physical book in over a year.
2. Board games/LEGO - also taking up a fair bit of space, I may try to sell/donate these as well. The board games are pretty niche (mostly military history style wargames), but there is a market for them, it is just finding the energy to sell/ship them that is a problem. (if you are wondering why someone in their fifties would have LEGO, just think of them as really expensive jigsaw puzzles. 🙂
3. I went through a couple of garbage bags of old clothes - some of which could be salvaged for donation, other stuff I don't know why I didn't throw it out at the time. It is weird how much stuff I have found that I have no idea why I kept it in the first place.
The harder stuff - momento's, old letters, cards, photos etc. Well, I will leave that until the end.
Furniture - again, until the transition to a nomad's life, I will need it.