So you've got a new system (or you're using a trusty one!) and you can see all the tasks you have on your plate now, and the ones that are coming up. If you're anything like me, that leads to an overwhelming sense of:
MUST DO ALL THE TASKS NOW
which inevitably leads to this cycle:
(Full description of the adult task cycle here!) But in all seriousness, the more I have on my plate, the more likely it is that I'm going to fall off the productivity wagon and get nothing done at all. So creating realistic milestones is key to managing my workload and giving me goals I can actually achieve. Meeting my goals makes me feel good, which makes me more motivated to do it again. That's the cycle I want to stay in.
So how do you set a good milestone?
When considering your milestones, start with the absolute deadline first. When do you have to have this thing finished and completed by? This can be scary to face, but knowing the timeframe is the most important step.
Next, look at the rest of the tasks. What else is on your plate right now? What will be added (or taken off) your plate between now and the deadline? Often, the problems with deadline setting is not the work on that project, but the other things that pop up and distract you from the project at hand. Zooming out to see everything on your plate can help you make reasonable choices about what you can dedicate and when.
Break up the work into reasonable chunks. Working on a dissertation proposal? Break that big project into its smaller pieces: Assemble an outline, complete preliminary research, draft the introduction, send draft to writing group, send to advisor, complete revisions, etc. Then space those out, starting from the last tasks all the way to the first steps. You can pace them equally (one milestone every two weeks) or according to the amount of work you estimate (longer for the research collection and reading, less for the outlining once that's completed) or spread them out based on your overall schedule - or some combination of those strategies!
But whatever way you pace them out, I'd advise you to leave a buffer at the end. Unexpected things will come up - and even if they don't, you'll be finished early! Do you have collaborators? Add time to the buffer. Are you working with a piece of complicated technology, software, or with lab/fieldwork research? Add time to the buffer. Are your deadlines close to other deadlines? Add to the buffer.
And here's the last, most important piece of advice! Every time you reach a milestone date, whether the task is finished or not, set some time aside to evaluate your progress. What's working well? What needs more support? Do other milestone dates have to shift? Update your plan, and resist the urge to "just make up for lost time" on the next date. The more you can learn to be flexible and realistic with your milestone deadlines, the better you will become at estimating how long a task will take, and when you need to call in more support.
Setting milestone dates is an art as much as it's a science - but being able to plan realistic workflows for yourself will allow you to see much more clearly when you're working in the way you need to, and when you might need a little extra time, effort, or support, to meet a deadline. The more clarity you have throughout the process, the more you can avoid that last minute rush to finish everything, and just have a last minute rush to finish some things.