Do not start with the sentimental things
Everybody does, and it is why so many downsizes stall. The first box people open is a box of photographs, and the afternoon disappears — pleasantly, but it disappears, and nothing has been decided.
Start somewhere with no feeling in it at all. The garage. The airing cupboard. The shed. You will get through a great deal, you will build some momentum, and the sentimental things will be easier when you reach them.
Measure the new place before you decide anything
Not the rooms — the walls, the doorways and the turns. A wall that will take a particular piece is a fact you can decide against. A room that "should be fine" is a hope, and hopes do not survive a staircase.
While you are there, count what is already built in. The storage you are losing is almost always fitted: the loft, the cellar, the wall of wardrobes, the cupboard under the stairs.
Sort into four, not two
Keeping and not-keeping is too blunt, and it is why the not-keeping pile never gets dealt with. There are four real destinations:
- The new place — it fits, you use it, it is coming.
- On to family — somebody actually wants it and has measured.
- Into storage — you are genuinely not ready to decide, and you will look again.
- Cleared — sold, donated, recycled or disposed of.
Be honest about the storage pile
It is the useful category and the dangerous one. Deferring a decision during a move is entirely reasonable. Deferring it indefinitely turns a storage unit into something your children will deal with, which is the opposite of what a downsize is for.
Agree with yourself when you will look at the list again. Once the new place has settled is usually about right.
Ask family early and plainly
Not "would you like it?" but "do you want it, and have you measured?" It is a more awkward question and it is far kinder than a wardrobe that sits in a garage for a year before being quietly got rid of.
You do not have to do it in one go
Clearing first, so the house shows better. Family deliveries before the main day. A storage run to take the pressure off. Stages cost a little more than a single day and are very much easier.