How do you decide what is a milestone or a deadline and when it is? I use todo lists and they work well, but like Rinkuhero said one might suffer from not having deadlines & milestones. I think I have at least partially this problem.
For example right now I have big list of things in my todo, but can't really come up good deadline or milestone from them. In sense I don't know how to group myriad of little tasks, even if they have a same theme (like menus, enemy graphics etc.) and assigning unique deadline for each small task seems a bit overkill to me.
To rehash the question, how do you group tasks into meaningful groups which then can be set a deadline? After all many tasks are interconnected.
this depends on the game, but i generally group tasks into big groups of 20-50 tasks. i don't usually set a group of tasks as a milestone however. instead i set several time-consuming individual tasks as the milestone, and the other tasks can be done whenever.
example, my current milestone for SD is "finish all ~40 dream mode levels". but in order to finish those levels, certain other tasks must also be done, such as converting creatures to dream mode (so that they have specific actions / movement patterns / behaviors in that mode), as well as working on the infrastructure related to those levels (such as a game over message, a high score system) and the visuals/audio related to those levels (sound effects, particle effects)
that's a pretty big milestone though (so far it's been 5 months, i started this one in the beginning of february). i've had smaller milestones that have only taken a month or so, such as "write all the remaining dialogue in the game" (as a first draft, just having everything done but not edited). another one was 'add the options menu and get most of the different game options in that menu working', which also took about a month
during those periods i often work on things not related to the milestone or not necessary for it, just as a break. you don't have to work on everything in a specific order, you can do what's fun sometimes. for instance during my current 5 month milestone i took a break for about 2-3 weeks just to work on some of the music (typing up sheet music into midi notation software, then arranging it and working with others to arrange it better)
so what i'd suggest is to leave most of the tasks in one lump, but for the current milestone, arrange the necessary tasks for that milestone. i also feel milestones should be something big, something *noticeable by players*, not something minor. something that you, as a player of your own game, will be happy with to have finished, such as "being able to play the game to the end, with an ending", or "adding joystick controls", or "add a new playable character", something like that, not something under the hood that only you as a developer care about
here's some more milestones i've had for SD, from memory, in rough order of when i did them
- the basic engine: movement controls / title screen / loading screen / new game / continue / saving / loading / etc.
- coding the game objects and creatures (not all of them, just getting some of each of the major entities in the game working). in other words, adding all the basic 'object types'
- adding the player's abilities (the actions the player can do, abilities the player can collect/equip and use)
- adding the level editor and map system, and a test level, and an area transition effect
- adding sound effects, music, and particle effects into the game, as well as other special visual effects like reflections and whatnot (what one indie game video called "juice")
- making more areas of the game, more creatures, more interactive map objects (this took most of the time, probably like two full years, within which i had smaller milestones like the ones below)
- adding an intro, and endings, and "bosses"
- adding various "systems" into the game (memory cell system, terraforming system, teleport tree system, godstatue system, function upgrading system, camp mode system, weather system, soundscape system, an "ability stealing" system (where the player acquires abilities from the creatures), etc. -- each of these was a small milestone which added a lot to the game)