Rambles: Milestones and Leveling Sucks.

   Disclaimer: In this blog I do talk about milestones as they are typically used in the modern culture of play from 5e's context. The rule for milestones in the 5e DMG are different and brings up some interesting ideas, but this already got a bit long as a blog so maybe ill discuss this in the future! In this blog, when I'm talking about milestones Im talking about session based or story-based full level ups without XP. I am also discussing this entirely within my own play experience so this might not be the case for you.

    During my time running games I can't really think of a time I did not use milestones. Recently I started thinking about them again critically because I am designing my own game system to run my dream game, while also trying to be in line with the play culture from 5e for new player appeal. I was working on a write up of my dream system for advancement and when I got to the idea of milestones and realized that I didn't know if I even liked them. I kept writing until it spawned into my first blog post as I kept trying to work it out.

    So what actually are milestones? For most people coming from 5e, milestones are the moment that the dungeon master in there game grants them a level up due to the events of the handful of sessions since the last milestone. After you kill the dragon, you get the milestone. Or finish a quest or scenario, you get a milestone. Or its been just a bit since you got a milestone. These are all milestones because they are advancement after something in the campaign occurred. The something there varies, and I have been lucky enough to be in scenarios with my players that I can make it a definite achievement that the players can work towards freely without a set progression. One of my favourite campaigns to date, I had a level-up milestone tied to entering the deepest section of a dungeon, where a dragon so filled the halls with ash that it was the major danger the area posed. This is different from the times my players had  4-5 sessions without progress due to some unforeseen problems, or just short and slow sessions. There the something that awarded them with the level up was that they played 4 sessions of my favourite game with me.

     Those two examples highlighted something for me when I thought about them though. The first case I enjoyed the milestones. But the majority of cases looked like the second. I thought these didn't contribute to the games sense of achievement and fun. That brought me to think about how milestones kinda suck.

     The differences highlight why and when milestones suck. When a milestone sucks, its usually for one of the following reasons:

• Its completely arbitrary or for no established goal.
• Its retroactively applied and represented no committed effort.
• The milestone wasn't arbitrary or retroactive, but did provide a railroad or a lack of player freedom.
• The milestone provides the only feeling of mechanical advancement every few sessions, leaving some session to feel like 'nothing happened'
  

    The first two are obvious because they are the known flaws in milestones. However lets dig into the first two for the moment. Milestones are usually arbitrary, and this contributes to them falling flat because they are not tied to any actual achievement. This matters because these deprives the game of any mechanically rewarded goal. There is no reason to stick to a goal mechanically because anything that happens that is significant enough be awarded with a milestones, regardless of it was a sessions long struggle or a random encounter almost wiping the party. This flatness gets doubled when there wasn't even anything that happened that was notable enough to merit a milestone apart from the fact that sessions occurred. This is what I meant by retroactive application of milestones. Lets say for example a few sessions occurred where there was a loss of direction. Many leads got thrown into the ring and decision paralysis caused the party to explores all of them without firmly committing to any. After a few sessions of this, with maybe some challenges thrown in like random encounters or maybe a bit of PC drama, your players ask if they level up and you decide that the last few sessions of asking questions and exploring around has warranted a level up. Something did happen as players investigated an area and a few stories progressed, but not one was the focus. What had occurred since the last milestone was deemed worth an advancement regardless if was actually a player goal. It just doesn't give much weight to the achievement.

    Most of my examples here come from my more recent games. Milestones were always my go to for advancement since my first days as a DM, but I never had as much issue with them until recently. That was because my recent games tried to lean more into a player driven style of game. Rather than me preparing linear arcs, I at least wanted my players to plot the path forward in the world, choose their own enemies. The quality that made them work in the old days was that I was a bit of a railroader back then (I blame The Adventure Zone!). Its simple to address the two most obvious flaws of the system if you prep this way. If you know that the players must go somewhere then the milestones can be set in advance. For example, if you know that the players are going to go kill a dragon, and that the buy in or concept of the game would have them stick to that objective then the milestone ceases to be arbitrary or untelegraphed to players. 

    The flaw is that this does limit player agency to make there own objectives to a degree. You can try and prep multiple routes to the milestone, or try and let the players find there own way there, but all roads must still lead to Rome. This is workable for sure but not the best if you really want the players in the driver's seat like I have been enjoying.

    The last issue, and I think the one that ended up souring me on milestones, was that they suffer from a pacing issue. Most people think a level up milestone should come every few sessions in an ideal pacing (The 5e DMG even agrees with a level every 2-3 sessions). The issue is that I don't think there has been a time where this actually occurred naturally for my games. In most cases the level up comes way to fast, creating a bit of dissonance in the experience of the party advancing (going from peasants to gods in a month of in game time). The other end has my players not reaching established milestones because of distractions or other issues. This can create a feeling of nothing changing or no progress being made. The worst part of this is that usually when this unsatisfactory pacing happens, there is a pressure to fix it by making the milestone to level up a bit more arbitrary or to reward retroactive goals. So were back to the first two reasons again!

     So if I don't enjoy using them inside my campaigns, why don't I just switch to XP fully as the rules intend? Well to be honest, my party and I dislike tracking tallies of XP. There was also an issue that combat and gold for XP created specific mechanical motivations to engage in those activities to advance. A lot of my players didn't feel very connected to playing characters where combat or plundering were the means to achieve their particular ends. While both are flexible, they never connected or felt fun for my game. They also did add some pacing issues as the campaign had to stop to properly divide XP after each fight and such.

     I've done a lot of complaining here, but I do have some conclusions and reworks of the milestone system I want to get to. They are just going to be coming later on as I tinker with systems myself, but this organizes my thoughts about why I need a replacement in the first place. If you have any grievances with milestones or systems you have used as alternatives I would love to hear them!