Three shoeboxes, an album with nothing written in it, and a drawer of paperwork nobody can throw away. Where to start, and what is actually worth keeping.
Label before you organise. The single most valuable thing you can do with a box of family photographs is sit down with the oldest person who can still name the faces and write the names down, even if the photographs stay in the same box afterwards. Sorting can wait; the naming cannot.
Do the naming first
Everything else can be done later or by somebody else. Naming cannot, because it depends on a person who will not always be there.
Sit down with whoever is oldest, or whoever knew that side of the family, with the box between you. Go through the photographs one at a time and write, for each one: who, where, roughly when. Pencil on the back, or a number on the back and a note in a book, or a photograph of the photograph with a caption on your phone. Any system beats no system.
Two hours of this is worth more than a year of scanning.
While you are there, record the conversation. It will be full of things that are not on the back of any photograph: who was not speaking to whom, why they were at that beach, what happened to him afterwards. The recording guide covers the practical side, though for this you barely need it: a phone on the table is enough.
Sorting, if you want to
Only once naming is done.
By person, then roughly by decade. Not by exact date, which is unknowable and unnecessary.
Pull out the ones that carry a story, not the ones that are best photographically. A blurred picture of a shop front with the family name over the door is worth more than a good portrait of an unknown cousin.
Put the duplicates in one envelope. Older families often have five copies of the same studio portrait.
Do not throw anything out on the first pass. You cannot get it back, and the thing you think is nothing is often the thing that dates a whole period.
Paper: what is worth keeping
More than people expect, though not all of it.
Worth keeping: letters, postcards, diaries, certificates, indenture and apprenticeship papers, service records, wage slips, rent books, works outing programmes, order of service cards, school reports, anything handwritten, anything with an address on it.
Usually not: bank statements, insurance renewals, receipts, instruction manuals, the great mass of modern admin. The exception is anything that names a place they lived or worked and dates it.
A useful rule: if it tells you where somebody was, what they earned, or what they were expected to do, it is evidence about a life. If it only tells you a company existed, it is paper.
Letters need one extra step. Read them before deciding, and be ready for the fact that some of them will contain things the family does not know. Think about that before other people are invited to read.
Scanning, without it taking a year
Scanning is the part that stalls most families, because they start with the whole box.
Do the fifty that matter. Phone camera, good daylight, flat surface, no flash. A phone photograph of a photograph is not archival, and it is entirely good enough to use in a book and to share with family.
Anything fragile, oversized or genuinely old, leave alone until you can do it properly or have it done.
Back it up twice, and name the folders with names in them, not IMG_4021.
Turning it into something readable
Photographs and paper on their own are a box. What makes them a story is the connective tissue: who this was, why they were there, what happened next.
That connective tissue lives in people’s heads, which is why the naming session matters more than the scanning. If you want the finished result to be something a grandchild will read, the order is: name it, record the talk around it, then write it.
If you would rather hand that over, it is a normal starting point for what I do, particularly after somebody has died. Tell me what you have and I will tell you whether there is enough to work with.