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Currently I have a few tasks that I want to do, such as reading book X, reading blog Y, listening to podcast Z, watching video W. I do them usually in my free time when I'm done with urgent work and I pick one that is most interesting. I use a time tracking tool to see how much time I spend on each task, so that I don't only read blogs all day, but also have time to read some chapters from a book.

Would I be able to progress faster with my tasks if I scheduled them explicitly in a calendar or in a gantt chart instead of just picking one whenever I have free time? In other words, should I set deadlines for myself or should I just take my time and finish a task whenever I finish it?

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Scheduling tasks that do not really have a particular target time would just create an overhead in your system, where you'd have to keep rescheduling them whenever you didn't get them finished that day or even have rather worked on other things.

Since they're all non-urgent, though they sure may be important and even critical for your personal goals, I think you should allow the flexibility to pick what's more to your mood in a given moment.

Having said that, if you want to benefit from some focus, which would make finishing them off more efficient, since you keep data on when you have last worked on a task you already use a time-tracking tool. So a mindset like in the Pomodoro Technique could fit well, where you try to focus and get finished with tasks you started on, though it may take multiple sittings to do so--no problem with that.

Still I think it's important not to force yourself to do any task just because it's the one you have last worked on. One other technique that I appreciate very much for lists of non-urgent tasks is Structured Procrastination. In fact, if you read the essay you will learn that you can (and should) also put extremely urgent tasks there, at the very top of the list, but ones that would, on closer inspection, not be such a big deal to miss. So it depends on the nature of your urgent work.

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Thanks a lot. I'll try the Pomodoro technique. Actually, it's already on my list of books to read (the pdf). I find Structured Procrastination rather interesting. I have a few things on top of my lists that have been there for a year now, haha. I've been doing other apparently not so important tasks. At the same time, I'm not really sure that missing the deadline for an assignment could work. So maybe I should put that under not so urgent, so I actually do it on time :) – siamii Dec 15 '11 at 2:11
Yes, if you consider how much those list-toppers have allowed you to willingly accomplish over the months, it's so much more value than they would provide themselves. Willpower is a limited resource and often better spent on setting habits (like the Pomodoro Technique) than forcing yourself to do your most dreaded work. I wanted to also mention GTD in my answer but felt it might be too much, not sure if you know it, but after you get used to Pomodoro you can search this website for questions regarding how to integrate the two. – Vic Goldfeld Dec 15 '11 at 5:53
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Setting good habits is key to an effective workflow because it can be relied upon (unlike willpower). I've been using GTD for a while now. Basically in my system right now, I have Google Tasks for GTD lists (next actions, some day maybe, waiting for), Google Calendar for scheduling, Diigo for keeping references, Toggl for tracking time and Chrome Nanny for keeping focus. You can google the names of these products if you're interested. Not strictly related to the question, but thought I might share. – siamii Dec 15 '11 at 7:32
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An update: Recently, I haven't had break from work for two months, so I focused on my personal projects. My experience was that Parkinson's law is very real. In case of infinite time available, i.e. without deadline, tasks fill up infinite time and progress painstakingly slow. Procrastination and distraction become really big issues. So I've switched to scheduling and setting deadlines for my personal projects as well. For example, "read X pages by next Sunday from book Y". I'll give an update in a few months. – siamii Feb 7 '12 at 18:54
Another thing I was wondering if I should also set penalties for myself when I miss a deadline and what the penalty should be. Otherwise, I have a feeling the deadlines by themselves wouldn't be very effective. – siamii Feb 7 '12 at 18:54
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