Understood, but you are putting the bullet train before the horse here.

Journaling is good. Keep doing that. Writing more is how you write better. This makes turning your notes into legible materials easier with time.

Encrypting your notes is good. Keep doing that. Developing a practice of pervasive encryption and proper opsec around that practice is good for you and good for your comrades.

Designing a dead man's switch into your journaling workflow will sap all the energy you should have been putting into journaling and leave you with a recurring chore.

This recurring chore will make your opsec worse. By investing in the theatre of it, you will dull your good sense and you will slip up and include information you shouldn't have.

This recurring chore is radioactive. Failing to do the dishes makes your place unpleasant and may annoy your roommates. Failing to maintain your dead man's switch will get your cadre hanged in the square.

Most importantly: a digital dead man's switch is not functional. If you want this to work as stated, the actual process is as follows:

1. Acquire long-term, secure, physical storage. Safe deposit box, vault, things of this nature. Ideally multiple.
2. Make multiple copies of your private key. Physical paper copies, magnetic tape backups, some digital storage media for flavor. Store these physical objects in the secure physical storage locations. 2.a. If you want to be real cloak-and-dagger about it, use different keys for different sensitivity levels, then encrypt the contents for each key of that level or higher.
3. Publish your encrypted notes widely. Ensure multiple copies are available at all times. Back your notes up to multiple storage providers, keep local copies, print armored output out on paper, whatever.
4. Develop a contingency plan that ensures that access to private key material is conveyed to trusted parties. This should be durable and include plenty of redundancy. Automated emails with access credentials for physical storage, ads placed in print papers with instructions (or even online ads if you're wild about it), a tontine. Whatever works. 4.a. If you've gone with layered keys, you may, for instance, publish the private key and authentication phrase for the lowest sensitivity content publicly. That content may contain further steps that can be enacted by trusted (or unknown) parties to unlock the rest, or you may have the other keys also be published at a later date.

When the switch is tripped (RIP), the meeting minutes for the People's Front of Peoria will be the hottest ARG of the millennium and all the people who value the work they can recover will scream to the heavens "why didn't they publish this when we could act on it?!"