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Overthinking is the curse of the solo role-player, so what better way to break the habit than to launch right into the middle of the action - no preparation, worldbuilding or prior thought required.
We use Knave, its solo supplement A Lonely Knave and a host of other random table heavy books - mostly centered around the OSR sphere - to go back to basics and embrace the spirit of letting the dice take the lead.
This approach works well with systems like Knave, original (A)D&D or the various B/X clones (e.g. Swords & Wizardry, Old School Essentials, etc.).
All you need on top of that is some way to emulate a DM (e.g. Mythic Emulator, A Lonely Knave, Solo Adventurers Toolbox), some kind of bestiary to draw monsters and the occasional random encounter table from and you're off to the races.
Let the rolling begin!
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