Leveling Up Your Background, Part Three

This is the conclusion of my series on advancing your background. If you’ve forgotten what the heck is going on here, go back to Part One.

Part One | Part Two | Part Three


The term “sage” typically carries connotations of advanced status – something more like the endpoint of a nonexistent “Academic” or “Scholar” background. Sort of the same problem as “entertainer,” so… welcome to the same solution!

Legendary sages have made significant, lasting contributions to the scholarship on one or more major topics. A group of at least three students (using the acolyte, commoner, cultist, scout, spy, or thug stat blocks, and adding proficiency in Arcana and History) come to study at your feet. There are often a greater number of students, but you can always convince three of them to help you with any task, no matter how demeaning. You’re obligated to teach them from time to time, but that’s something you can make one of the other students do in your place.

Furthermore, you can gather more information when you spend at least 1 minute studying a magical effect. Roll an Intelligence (Arcana) check against DC 15. On a success, you can choose two of the following questions for the DM to answer.

  • Was this magical effect created by a person, a creature, a deity, an item, or an anomalous event?
  • Does the personal signature of this magic resemble that of any spellcaster I have previously encountered?
  • Approximately how long ago was this magical effect created?
  • If a spell was used to create this effect, what level was the spell slot?
  • If the magical effect is an item or comes from an item, what is its rarity?

Once you use this feature, you can’t use it on the same magical effect again for 24 hours.


As an able sailor you might, with time, earn promotions on a ship. (Consider developing a specialization within the crew, and moving into one of the nautical backgrounds of Ghosts of Saltmarsh or the forthcoming Seas of Vodari using the Changing Your Background rules.) You also might purchase, steal, or receive command of a ship. It’s not until you’ve completed a risky voyage or brought the ship through a major naval battle that you can be counted a famed captain

A famed captain has the reputation to recruit crew members or extra muscle in almost any port. You can recruit up to six thugs for the promise of a share of future spoils, or up to twelve thugs for half pay up front, with one hour of work. These characters also have proficiency in water vehicles.

Furthermore, you know how to lead by example to rally your crew. When you succeed a Strength (Athletics) check that isn’t part of a shove or grapple, you can choose one creature that can see you. That creature gains temporary hit points equal to half your level. While a creature has any of these temporary hit points remaining, it ignores the effects of the frightened condition. You can use this feature once, and regain use of it when you finish a short or long rest.

Sailor (Pirate)

A pirate follows a similar trajectory to a sailor. Maybe they specialize within a crew, earn and defend a captaincy, or come in from the cold and become a privateer. 

As an alternative to the second feature of famed captain, you can use threats and browbeating to shock your crew out of a stupor. As a reaction when a creature who can hear you suffers the stunned condition from failing a saving throw, you can unleash a stream of invective and roll a Charisma (Intimidation) check against the original saving throw DC. On a success, the stunned condition ends for that creature. A creature can only benefit from this feature once, and regains the ability to benefit from it when it finishes a short or long rest.


If you’re adopting my rules for changing backgrounds as part of character growth in the story, I imagine that a ton of characters spend some time as a Soldier before leaving it behind. Two of the most common outs are knighthood (leading to Noble – Knight) or receiving one or more estates for your valor (Noble). Since “officer” is already an option for your Specialty as a Soldier, I’d rather avoid that, too. For that matter, check out my Enforcer background. What soldiers can do is receive a job as a palace guard. (Etymologically, this is the same as becoming a paladin, but never mind that.)

A palace guard has both literal and figurative access to the halls of power, such as few others outside the nobility can dream of. If you want to speak to your monarch, a high-ranking clergy member, a noble, or an army officer, life as a palace guard means you can create the opportunity without even leaving home. If using the Carousing rules from XGTE, you can carouse with the upper class for half cost, and you always have access.

Furthermore, you learn how to intervene in a melee to keep your friends and charges safe. When a creature within your reach fails a Strength (Athletics) or Dexterity (Acrobatics) check to resist a shove or grapple, you can roll a Strength (Athletics) or Dexterity (Acrobatics) check as a reaction. The creature who failed the check can use your result in place of its own if your result is higher.


Much like the Hermit, Urchin is a starting point that you leave behind. An urchin protag is one of the main ways you know you are reading a Bildungsroman. (It was English Lit that brung me to the sorry state you see me in now.) You don’t necessarily even leave poverty – Charlatan, Criminal, Entertainer, Folk Hero, Sailor, and Soldier can all be dirt-poor next steps. I’d suggest that the most in-theme leveled-up background for an urchin to get to in one step is the guildmaster, in a very Oliver Twist kind of way.


That’s the end of the Leveling Up Your Background series for the Player’s Handbook backgrounds. Please let me know what you think of this approach. I’m interested in revising and cleaning up this text to the point that I’d feel good publishing it as a PDF on DTRPG or, more likely, the DM’s Guild.

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