Somebody leaves and you are handed their work. Or a relative dies and there is a laptop, and on it a decade of writing that nobody has ever read.
Both situations produce the same paralysis, and it is not a technical one. The technical part — opening files, searching them — is easy. The difficulty is that you are holding a document that was written by someone who did not expect you to read it, and there is no obvious rule for what to do with that.
First, the question about reading
Before any organising, one decision: is this material you should be reading at all?
Work notes, handed over deliberately. Yes. That is what a handover is, and the person wrote it expecting exactly this.
Work notes found on a machine, not handed over. More care. A departed colleague's personal file may contain their own frustrations, their salary conversations, their private assessment of you. Look for what you need to do the job and stop when you have it. There is no obligation to read someone's diary because it happened to be on a work laptop.
A relative's private writing. The hard one, and it deserves a real answer rather than a technical one.
About a relative's journals
There is no rule here and anyone offering one is overreaching. What can be offered is the set of considerations people find useful.
Look for a stated wish first. In a will, a letter, a note at the front. People sometimes leave one and it is frequently missed, because nobody thinks to look for it before opening the files.
Consider that they knew they would die and did not destroy it. That is not consent. It is also not nothing — for a lot of people the journal was left because it was theirs and they were not going to spend their last months curating, and they would not have wanted it read.
Slower is better. There is no deadline. Deciding not to read something now does not prevent reading it in five years; reading it now cannot be undone, and things read in grief land differently than the same words read later.
A journal is not a message to you. This is the observation people find most useful afterwards. Journals are where people put the worst version of a bad week, because they had nowhere else. Reading a difficult passage as a considered summary of what they thought — of you, of themselves, of anything — is almost always a misreading. It was Tuesday, and they were angry, and they wrote it down instead of saying it.
Whatever you decide, back it up first. That decision does not have to be made under time pressure and it certainly should not be made irreversibly.
The practical part: making it searchable
Once you have decided what to engage with, the technical problem is straightforward.
Copy everything before touching anything. One copy on a separate disk, untouched. Everything else happens on a working copy. This is the whole insurance policy and it takes ten minutes.
Establish what format it is in. Plain files are trivial. An app's database is workable — SQLite is an open format and readable by free tools if the original app is gone. A proprietary blob may need the original software, which is a reason to try installing it before anything expires.
Get it into text if you can. Whatever the source, an export to Markdown or plain text into a folder means Spotlight indexes it and grep finds anything Spotlight misses. That is a working search over somebody's entire collection for about an hour of effort.
Do not reorganise. Strong recommendation. Their structure encodes their thinking, and imposing yours destroys information you do not yet know you need — most obviously the order in which they wrote things, which is often the most informative property of the whole collection. Search, do not sort.
What to look for in work notes
If this is a professional handover, the useful material is narrower than the volume suggests.
The undocumented facts. The reason something is done a strange way. The client who needs a phone call. The system that fails in a particular manner. These are what a handover document is supposed to capture and frequently does not.
Who they talked to. Their notes name people, and those people know things. Often the most valuable output of reading somebody's notes is a list of six names to go and ask.
What was in flight, and its real state. Distinct from its reported state, which is what the shared tracker has.
Their judgement. What they thought was actually wrong. Worth reading and worth weighing — they had context you do not, and they also had frustrations that may have coloured it.
You can usually extract all of this in an afternoon with search, without reading the collection front to back.
Then write down what you learned
The step everybody skips, and the reason the same loss happens again in two years.
Reading somebody's notes produces understanding that exists nowhere in writing. Put it somewhere: a short document of what you found, where the material is, and what the six important facts turned out to be.
Because the material itself is not the deliverable. Nobody will read a colleague's decade of notes twice, and if you do not extract the useful part now, the collection reverts to an archive nobody opens — and the fact that you once understood it is lost the same way theirs was.
For your own collection
The obvious corollary, and it is a two-minute job.
Whoever inherits your notes will face the same decisions with the same lack of guidance. You can remove that entirely by leaving one line somewhere findable: what should be kept, what should be read, what should not, and what should be destroyed. It costs nothing to write and it converts an impossible decision into an instruction.
That plus where the material is and how to get into it is the whole of a digital estate for notes, and it is worth doing while it is easy.
The honest version
The technical half of this is an afternoon. The other half is not a technical problem and there is no correct answer — only the observation that reading cannot be undone, backing up can always be done first, and nothing here has a deadline.
Cyanote is on the easy side of the technical question by construction: everything is in one SQLite database on the machine, in an open, documented format that outlives any particular app, and it exports to one readable JSON file. There is no account to recover and nobody here to ask, which is the guarantee working as intended — and the reason to leave a line about what you want done, while you can.