How do you XP in D&D?

Unknown Mathematician Levels Up. Found here. 

Unknown Mathematician Levels Up. Found here

This was brought on by a conversation with thedicenerds and glasscannonpod on twitter. It basically breaks down to this:

What are some options for leveling, and how should we level our characters? 

Here are the main options that I found while scouring the internet in my old DM guides.

Milestone Leveling
Milestone leveling requires leveling up characters when they have completed a significant story arc, a set number of sessions, or whenever the DM "feels like it". I have read comments that some players really like milestone leveling. Players don't have to do experience point bookkeeping, levels just accumulate by fiat, and it might feel more natural if well woven into the plot. I discussed this with two of my group's regulars and they both did not like this idea. They found it arbitrary, and stated they really enjoyed the bookkeeping and anticipation of leveling up.

I think there is some merit to their criticism, we want to know we earned our level and for some reason adding up numbers provides a sense of achievement to my players. I really think this method could be used effectively if it was woven into the story (or combined with "Training" below). However, due to my players' objections, I don't think I'll be running this soon.

Quarter or Half-Leveling
Glasscannonpod mentioned quarter-leveling during the discussion. I had never heard of it before. Basically, as a person gains experience they are granted part of that level's benefits once they reach a quarter of a level. So if a character needs 2000xp to travel from level one to two, after 500xp a character gets improved hitpoints, the next 500xp they get their skill points, et cetera. This would obviously work well with milestone leveling.

I actually really like this for showing continuous improvement. If I were implementing this for 5th edition, I would probably only do half-leveling. The first half the character gets hit points, the second half gets class abilities. I don't think 5th edition classes have enough crunch to stretch over four "quarters" of a level.

Gold as XP
(Aside: There is a nice series of write ups on wealth and D&D by DM David.) This is a holdover from the first edition where looting gold brought XP. In the version that I am considering, I might make characters spend their hard won cash as XP. This could also be a method of burning up excess gold that you hand to the party and incentivizing the party to seek treasure for its own sake. The XP accumulates as long as the money spent is removed from directly influencing the game and spent in thematically appropriate ways. The cleric donates it to his church, the fighter spends it on her massive party, the rogue buries it (never to be used again), everyone builds a stronghold, et cetera.  I remember someone posting an article discussing halving the XP from monsters, then using the gold to compensate to an approximate 50/50 split, but I can't remember where I found it. I like the idea of spending the gold to increase experience, not just looting it, because it forces the players to make decisions about how to spend their adventuring dollar. Do you want that nice magic weapon or to level up? It could also be a nice role play opportunity, maybe bandits crash the character's fancy party.

For me, I keep my party cash poor, so I feel like this would be easy to implement (subtract the relevant experience from the monsters and then add the approximate amount of gold to compensate). I am not sure what the characters would do with all that cash, but that's not my problem. I discussed this with a couple of players and they were split. One (the barbarian) really liked the idea, the rogue was luke-warm. I think I might make my party hunt for gold.

Training
I never forced this on my players, but one of the variant leveling up rules requires that the characters train in order to level up. This rule is included in 1st, 2nd, and 3rd edition. I couldn't find it in 4th or 5th. Basically, a character has to find a sage, swordsman, or whomever that is of a high enough level to train them before a they can level up.

Just because Neil Nimblefingers, Rogue of the thieve’s guild, has managed to acquire 1,251 experience points does NOT mean that she suddenly becomes Neil Nimblefingers the footpad. The gaining of sufficient experience points is necessary to indicates that a character is eligible to gain a level of experience, but the actual award is a matter for you, the DM, to decide.

[. . .] [complex rules on how to determine how many weeks a person needs to train]

Initial study and/or training must be conducted under the tutelage of a charger of the same class and profession as the trainee.
— Gary Gygax, 1st Edition DM Guide (1979)

I like the idea, but doing this for each level is tedious. Let's make this easy for players in 5th Edition. Start by granting that some progression is going to be natural (you don't learn everything by getting a C-average in Wizarding College), but acknowledge there will be times where a character is going to need to find an sensei. We also know that mechanically the big power jumps are at the tiers of play. In D&D 5e there are 4 tiers of play:

  • 1st to 4th - Middling
  • 5th to 10th - Heroic
  • 11th to 16th - Paragon
  • 17th to 20th - Epic

Instead making a character find a trainer for every level, we could force a trainer for each tier. Now, as a burden to DM, these quests should be woven into the story and advance the plot. Maybe the sensei is easily found, but requires a great undertaking from the character to prove his worth. Maybe the imperial army keeps the level 20 magician under lock and key for she knows the secrets that doom the souls of... whomever.

A friendly reminder:
Some of these rules can cause additional unequal leveling if you have people that rotate in and out. For example, what if the characters find the ultimate treasure (and exchange it for XP!) on the weekend that Caroline is out of town. She loses out. Remember, optional rules should never be used to abuse or punish players, but to increase the fun of the game.