"It is all relative to the project size" is the first sort of unspoken thing to understand-whether a 1-day, 1-month, or 1-year project. But, one basic way, no matter which tool or process you are using, is to force rank every task that needs to be completed under a milestone. If there are sub-tasks, then force rank them too under their respective tasks. Force ranking just means you assign a linear priority to each task that says, do this task 1st, do this other task 2nd, etc. and with estimated time to complete, and no task can have an equal assignment to another(so there is no ambiguity), until you get through all the tasks for that day/milestone. Of course this is all relative. And adding in dependencies other things the team is doing is another level. But for a single person, you'll need to have broken down your tasks into a relative number that can be accomplished in a day or two--otherwise your planning is still too high level. Again, also depends on your process. If you are using Agile, you might not detail too far out or you might change in the middle and reorganize, but that's ok too--because that's the process. It takes a little time to get the hang of force ranking, but the process of force ranking itself is very informative and you'll learn from it. Best part is, the learning is all relative to the project scope so it can be applied/leverage for future similar projects. Hope that helps.
