#211 – Dictating to the Machine

by | Jul 18, 2026 | Health, House, Life | 0 comments

I’m writing this month’s post by dictating into my phone using Google’s GBoard keyboard, in Google Keep, because I’ve managed to acquire a repetitive stress injury in my right wrist. More on that shortly. It’s working surprisingly well, which is either a testament to how far voice recognition has come or a sign that I mumble less than I thought. 😊

The good news first, and there’s actually quite a bit of it.



The back is, for all practical purposes, back to what passes for normal. After the months I’ve had with it, I am not taking this for granted for even a single day. The stomach is still sorting itself out β€” the gut micro-biome takes time to repopulate after what the Flagyl put it through β€” but that’s just a matter of patience. Everything is moving in the right direction.



The condo purchase is imminent. I’m looking at the 3rd week of August for the actual transaction. I’ll be honest that parting with the money is not something I’m doing with a huge smile on my face, but the alternative β€” losing the place I’m happiest in to an unknown buyer β€” is worse. At least I have the ability to make a purchase of that magnitude. I’m not complaining. Much. 😊

The main project of the last two months has been getting my estate and executor documentation into a state I’m actually satisfied with. I mentioned last month that Kim’s death had exposed some serious gaps in my own arrangements. I think I’ve now closed most of them, and the system I’ve landed on is worth describing for anyone in a similar situation.


The core of it is my Proton ecosystem. Proton is a Swiss privacy-focused company that makes an email service, a password manager, and a cloud drive β€” all end-to-end encrypted, meaning only I can read the contents. My executors have a document that explains how to request emergency access to my Proton account in the event of my death. Once they’re in, they can access my Proton Drive, which contains a dedicated directory with everything they need: identification documents, all four wills, specific instructions for each country and each executor, contacts, account locations, and step-by-step guidance for what to do whether I die in Thailand or somewhere else entirely. I have originals of the wills etc., plus copies of the passports distributed but the instructions and how to access stuff is far more changeable.


The part I’m most pleased with is the update mechanism. Any changes I make to my instructions are automatically synced to the Proton Drive directory overnight. That means my executors always have access to the most current version of everything without me having to manually send updates every time something changes β€” which, given how frequently things do change, would be a nightmare.


Claude AI helped me work through the structure and logic of it, which I mention without embarrassment. Complex multi-country estate planning has a lot of moving parts and it helps to have something that can check your reasoning and flag what you’ve missed.


The one genuinely painful part of this process has been the Philippines, which requires what are called apostille documents β€” a specific form of internationally certified document authentication β€” and these currently cannot be obtained in Thailand. My concern remains that if local authorities here get hold of my original passports after my death, it could take months to retrieve them, which would delay probate proceedings in the Philippines and Singapore. I think there are workable solutions: Singapore will accept notarized copies of passports, and my business partners in the Philippines should be able to manage their end. But it’s the kind of thing you don’t want to be figuring out after the fact. In the end I’m trying to arrange in my instructions for my passports to be withheld from the police (giving them only notarized copies) and being hand carried to the Philippines.


One side note about this apostille thing. What a racket. Getting a document apostilled, a single document, can run hundreds of dollars. In Singapore $US500, In the USA, $700? What the f#*k?! Why?


Anyway. It’s done. It was a lot of work and I’m genuinely glad it’s behind me.


The repetitive stress injury came from the other major project I decided to tackle a few days ago: migrating nearly 22 years of journal entries into Obsidian.
Since 1998 I’ve kept my journals in a dedicated piece of software β€” one of those programs written and maintained by a single developer. It’s been reliable for 26 years, but I’ve started to wonder how much longer that will continue. Single-developer software is exactly as sustainable as that one person’s health, motivation, and circumstances allow. Beyond that, I’d found myself doing double work: writing diary entries in Obsidian (because that is my daily driver for notes) and then periodically copying them across to the journal software. No good reason for it. So I bit the bullet and did the full migration.
The result is good. Everything is now in one place and I’m very happy with it. My wrist, however, is not. Two days of recovery and counting. Hence the dictation. 😊

That’s July. Short month in terms of writing, for obvious reasons. Wrist permitting, August will be more expansive.

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