How do I declutter sentimental things without regretting it?

Normal decluttering questions do not work here. "Have I used it in a year" is meaningless for a christening gown, and "could I replace it" is meaningless for a letter. Sentimental objects need a different test, and they need to be done last, when you have made a few hundred easier decisions and got better at deciding.

Step by step

1. Do this category last, and only when you are well.Sentimental sorting after a bereavement, during an illness or in the week before a move produces decisions people regret. If a move is forcing the timing, box it unsorted and move it, and sort it in the new house when the pressure has gone.
2. Gather one sentimental category at a time.All the photographs, or all the children's schoolwork, or all of one person's things. Mixing categories makes it much harder, because each type needs a different question.
3. Separate the memory from the object.Ask what specifically you are keeping. If the answer is a particular grandmother, twelve of her ornaments do not hold twelve times as much of her. One does. This single reframing removes more volume than anything else.
4. Sort into carriers and companions.Carriers hold the memory on their own — a wedding ring, a specific letter, a photograph of a person. Companions were merely present — the box it came in, forty duplicate holiday snaps, the third-best mug. Companions can go without loss.
5. Photograph before disposing, and do it properly.Flat on a plain surface, good daylight, one item per frame, with a note of what it was and whose it was. An unlabelled photograph of an object is worth very little in ten years. This works well for children's artwork, trophies, bulky gifts and clothing.
6. Set a container limit before you decide, not after.One box per person, or one shelf. Fixed. It converts an unlimited series of yes-or-no questions into a much easier ranking question — keeping this means that goes.
7. Return other people's things to them.If your adult children's belongings are in your loft, or your parents' things are in yours, they are not your decision to make. Give a generous but real deadline, and be clear about what happens afterwards.
8. Use a dated box for the genuine maybes.Sealed, labelled with a date six months ahead, out of the main living space. It removes the item without requiring a decision you are not ready to make.
9. Consider giving things to someone who will use them.A tool used by a nephew, china used at Christmas, a coat worn by someone who needs one. For many people this resolves the guilt that keeping was really about.
10. Accept that you will get a few wrong.You will. The alternative is a house you cannot move around in and a job you leave to somebody else. The safeguards above make the error rate low and the errors small.

Tips

• Guilt about what something cost is not sentiment. That money is gone whether you keep the object or not, and storing it does not recover any of it.
• Inherited objects you never liked are allowed to go. Being given something does not create an obligation to house it for the rest of your life.
• If a whole category is unbearable, do a different one and come back. Progress elsewhere makes the hard category easier, not harder.
• Scan letters and documents at a high enough quality to read the handwriting, and back the scans up somewhere that is not the same building.
• Where several family members might want the same thing, ask before disposing. It is a five-minute message that prevents a permanent grievance.

Common mistakes

• Starting with sentimental items because they are the biggest pile — They are the hardest decisions, and you will make them badly with no practice. Almost everyone who starts here stops within an hour and does not resume.
• Keeping whole containers unopened because opening them is upsetting — The distress is deferred, not avoided, and it is usually deferred onto someone else. Opening one box with someone else present is far easier than opening twelve alone.
• Photographing objects without labelling the photographs — In ten years a folder of unlabelled object photographs is close to worthless, which defeats the entire purpose of taking them.
• Storing sentimental things in a loft or garage — Heat cycling, damp and pests destroy paper, textiles and photographs — the exact categories most likely to be sentimental. The things you care most about are in the worst place in the house.

Questions people ask