Since Dungeons & Dragons is anachronistic, most people, and basically every player character, know how to write. But what about those that know how to write and count better? The late middle ages were a time when there was a rapid need for more writers, more accountants. Guilds needed to track the money they were bringing in.
If your D&D world has many guilds it would have many clerks. Some of those clerks may get bored of quill and ink, or precisely measuring liquids, or whatever mundane task their employer has for them — so they head out on adventures, which is what happened in real life too. Lots of clerks got involved with murdering.
You are someone who counts fast, keeps precise notes, reads for others, writes for others. You are meticulous and detailed. When
Skill Proficiencies: Investigation, Insight
Tool Proficiencies: Calligrapher’s Tools
Languages: One language
Equipment: Common clothes, tabard, abacus, merchant’s scale, jar (precisely 1 quart), pouch, signet ring, 10 gp
Feature: Measure Twice
You can rapidly and accurately account for large quantities of coins or other staples, assessing their value using just a single action. Clerks are also able to stretch large quantities of staples further than expected. If you need more than 50 of an item a Clerk needs 10% less of that item. For example, 900 ball bearings works just as well for a Clerk as 1000. Or if others would need 50′ of rope the Clerk can make do with 45′.
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Alternate Background: Tax Collector
You are a representative of the government, collecting fees and taxes for the services they provide. Maybe you work at a toll bridge, a city gate, or you wander to various farms. Some pay in gold, most in silver or even copper. You’ll take barter too. The Barony needs the funds however it can get them.
A just collector may go easy on a family in years of struggle. An unjust may continually take. Your character’s behavior and history is up to you.
The Tax collector has the same skills, tools, and languages as the Clerk. The difference is in their Feature and in their role in society.
Feature: Forgotten Refund
Knowing the ways of governments you are able to assume the debts of a group that owe. You can also find a way to get a tax refund for yourself or others, or avoid paying the full amount. If normally the government takes 10% you would only pay 5%. If you are short gold, you may visit another tax collector, if one can be found, to get 5 times your proficiency bonus as a refund.
Clerks were so common in the late middle ages they killed a lot of people. Which sounds a lot like D&D adventurers, so why not have a Background based on them. Sure, they could be represented by Sages and Acolytes or other thinkers.
But, I’ve watched too many Clerks movies, and so needed to honor the OG clerks in a special way. Don’t be murdered by clerks, be the clerks that murder.