Design Theory - Actual (?) Milestone Leveling for D&D 5e

11 Feb, 2025

TL;DR Replace XP with class focused Milestones, specifically, the features from the class table.

I have been exploring the OSR space in the last year and have fallen under the sway of their ideas, particularly the focus on diegetic effects like in Carin or Into the Odd. The milestone leveling system could easily be tied to in game effects but always ended up being DM fiat at our table. For those who don’t want to swap back to tracking XP, I propose the following:

How it functions

In order to reach the next level, you character must gain all the class features for that level. When that happens, they then get all their numeric upgrades (HP, proficiency bonus, etc.). As an example, the ranger Soveliss wants to go from 1st to 2nd level. In order to do so, he will need to learn a Fighting Technique (from the 4 available to 2014 PHB rangers) and learn 2 spells from the Ranger spell list. Once all of that is complete, the player then gains everything else from the class table, which in this case, is the hit points and the two 1st level spell slots. If there is nothing listed under the Features column in the class table then they usually gain the ability to cast the next level of spells which would be considered a class feature for this purpose.

Drawbacks

• Characters need time to train so the modern D&D storytelling style of imminent threats with no downtime will have to be slowed down.
• The DM now has an extra responsibility to provide these opportunities for leveling. In addition to providing the story beats, they should be sprinkling in these opportunities and rewards too.
• The class tables are not equal in their complexity to level up between the players, potentially leading to differences in levels within the party.
• D&D 5e is not built with this in mind so each of your players’ classes need a sanity check to ensure it isn’t too strong or difficult to progress. Multi-classing would require some specific rules to account for the implied time it takes to become a 1st level hero.

Benefits

• This method forces your players back into the world where they have to interact with specialists and more senior members of their class.
• Players have an pre-written, explicit list of personal quests to complete.
• It opens up opportunities for meaningful downtime activities. Finally a chance to spend all that gold!
• More meaningful choices come up, especially if they are mutually exclusive. Do we head to Baldur’s Gate so that the fighter can train with the Battlemasters, the Druid’s Grove so the druid can join the Circle of the Moon, or straight to the Cult of the Reptile God before they have time to prepare?

Some ideas on how to enable gaining class features:

• Spell scrolls could be a means to learning spells but it has to be different from the wizard’s key class ability to copy scrolls into their spellbook. Perhaps, the hermit can only teach you that spell if they have a text to follow.
  • This has the added benefit of a unexpectedly gaining a level from a chest with a random scroll in it instead of just a consumable that you forget is in your inventory for a few levels.
  • An alternative is spell lists aren’t known by the characters so they would have to see it in action or find a scroll in order to “know it exists” before attempting to learn it.
• Fighting styles (especially basic ones) can be easily taught by a fighter’s guild for a fee.
• If a player is stumped on where they could learn the next feature, they talk to a higher level NPC of the same class. I’m sure they would be happy to teach you what you want to know if you do this one little task for them…
• Ancient shrines and forgotten texts describe many things that are currently not known. Studying them could unlock the secret to a deeper understanding of your class, especially if you’re probably the highest level wizard around.
• When in doubt, pray! Visions from your god (or patron…) may reveal the quest you need to complete to receive higher level divine aid.

Conclusion

There is a lot of work to be done before you could drop this at a table but I think there is something workable here. I don’t play a lot of D&D at the moment so I probably won’t develop this much more but I would be interested to hear if others have had similar thoughts or even developed their own systems. If so, feel free to drop me a line at tonights.session@gmail.com.