Working From Home – Keeping Up with Deadlines

Deadlines are one of the hardest parts about working from home in my experience. Besides the fact that time isn’t real, it’s hard to conceptualize two weeks stretching before you and that number steadily going down. For me, once I set a two-week deadline, it feels two weeks away until about three days before. By then, you’re in crunch time and panicking because you hadn’t planned out your time the right way. Here’s how I try to manage deadlines:

First, write down the day it’s due

This probably seems self-explanatory, but for me “due in four days” and “due on Friday” mean different things Monday morning. Test out different ways of phrasing your deadlines to see what works for you.

Second, brain dump at the start of every day

This was a total game-changer when I first started doing this. At the start of every single day, whether I work that day or not, I review all of my tasks for the week. It helps assure me that I haven’t forgotten anything and reduces my anxiety, but it also reinforces the countdown that’s happening as deadlines approach.

Lastly, break your deadlines into milestones

Most of my contracts are broken into milestones, and I’ve taken to adopting this strategy with just about all of my projects (both personal and work-related). For example, if I have ten thousand words due in two weeks, and I take four total days off in that period, then I need to write at least one thousand words of that contract per working day to stay on track. Try breaking deadlines into small, bite-sized pieces and it will help deadlines feel more manageable while also making your daily tasks more concrete. “Write 1k words” is something I can mark done at the end of the day, whereas “Work on the project” is not.

This is how I stay on top of deadlines and make sure I’m not dropping any balls, but it took me quite a bit of trial and error to reach this point. I may even find an even better strategy in the future. Try out a few different techniques, don’t be afraid to experiment, and see where it takes you.

How do you keep track of deadlines? Do you use apps? Do you write things down in an actual notebook? Maybe you use a mix of both like me? Let me know in the comments!


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