For some years now I've been trying out various programs to handle time tracking, to-do lists, reminders, and so forth: MyLife Organized, ToDoList, Outlook, Thunderbird, half a dozen lame little freeware programs I've long since forgotten the details of, and even one or two attempts at writing my own. Of these, TDL is the closest and does in fact do a good job of planning out professional tasks and tracking time on them, but it doesn't quite manage the job of arranging my daily/weekly schedule. Specifically, it's too inflexible on a daily basis, and its reminders are a little too intrusive. So I'm looking for a program to replace TDL in this part of its duties.

Crucial features

  • Reminders. These must display on the desktop, must not steal focus and should be as efficient as possible to snooze for various lengths of time or dismiss until the next day. I'm not going to check a list to see what's current.
    • TDL's do steal focus, the enormous combobox of snooze times is a bit clunky, and there's no way to efficiently dismiss the reminder dialog without removing the reminder from future instances entirely (!).
    • Thunderbird's are about the same, although if memory serves the reminder at least sticks around on future recurrences.
  • Efficient recurrence. Most of my daily schedule can and should remain the same throughout the entire week, but each day has at least a few quirks, and the weekend has rather more, so the program must allow reuse on at least a days-per-week basis.
    • TDL is more than fine for this, with daily, n-daily, days-after-completion, weekly, days-per-week, n-weekly, weeks-after-completion, and so on available.
    • Thunderbird does OK on this as well.
    • I think Outlook does too, but it's been a while since I tried it.
  • Daily and weekly perspective of how every timeslot is filled. I need to make sure I'm not spinning my wheels. And yes, I do mean every: as of a few months ago, I schedule meals, sleep, reading or games for relaxation, professional development, webcomics, and so on besides the obvious "get stuff done to get paid".
    • TDL doesn't do well on this at present. In principle it's straightforward enough to see down to an entire week of task start/due dates and times, but in practice the display of recurrence beyond the next instance is non-existent and the resolution of short/precise tasks is maybe a couple pixels at best. So I mostly rely on a table with columns for times. I have a feature request that might help.
    • Outlook and Thunderbird are both good at this, displaying recurrences and with fairly high resolution.
  • Must display notification windows on Windows 8. I'd prefer a dedicated desktop program that collapses to a notification icon, since I don't actually have a browser open all the time, but I could probably work around the constraints of a web app if it works really well otherwise.
    • TDL is great here.
    • Thunderbird will, for mysterious and frustrating reasons, page itself out to disk almost all the time within a minute of starting up and continue paging out even while attempting to page in and display. I still use it for email at intervals, but leaving it running is not an option at present. There is, or was, an addon to collapse to the notification area, but I don't use that at present, obviously. (I'll be replacing my rather outdated 2GiB RAM machine in the future, but the time for that is not yet.)
    • Because of the above, web apps that rely on email reminders or RSS or the like are out. I don't like email reminders much anyway. XMPP might work (since Pidgin is always running), and I've seen one program that actually uses that, although it was unsuitable for other reasons.
    • Outlook is fine, although a bit heavyweight for my liking.

Things I'd like to have

  • Prioritized reminders. For example, a balloon popup for low-priority and an on-top (but unfocused) window for high-.
    • TDL just has the focus-stealing dialog, and usually it brings along the main window too.
  • Dynamic adjustments to the schedule. Sometimes a given timeslot takes longer (or shorter) than the usual, and I'd like to automatically push the next reminder back, and ideally collapse certain designated tasks all the way down to zero duration/no reminder to compensate for schedule slips.
    • TDL allows me to designate tasks however I like! But the reminders don't do anything with this, and all reminders are completely independent and will pop up in sequence if you wait too long.
  • Easy switching between different schedule plans. On any given weekday, I might be following one of two or three substantially different "profiles" (work at office, work from home, work in shop, etc), and it's not necessarily practical to schedule ahead of time.
    • TDL currently forces me to schedule fixed days (e.g. TTh) on which I will follow profile X.
    • I've never seen a program that supports this, so it's certainly not a deal-breaker, but man would this be handy.
  • Low/no price. I could program something myself*, and I have a lot more time than money, as well as a perhaps-irrational pennypinching mindset, so anything that's not free will make me think twice.
    • TDL and Thunderbird are fine on this; Outlook is OK in that I have a license for 2013 anyway.
    • Anything more than about $15 is highly likely to make me pick something else.
    • Subscriptions are out unless the pitch is extremely convincing and the price extremely reasonable.
    • Adware is a possibility, but nagware of any variety is not.
    • Trialware might actually work in this context, since I will certainly be using whatever I try every day, unlike the usual "use it once, then remember again two days before it expires" pattern.
  • Comments, multiple reminder sounds, task list filtering, categories, etc etc etc. The usual random metadata most good programs have.
    • TDL has somewhat spoiled me; it has more of these than anyone could need, although they don't do much more than affect display coloring and filtering.
    • Thunderbird is OK for this. Not amazing but it's not really a problem.
    • Outlook does pretty well, and I think it even has custom fields like TDL, but its filtering isn't quite as good last I checked.
  • Not made by Google or Apple.
    • I just don't like them. But I'm not stupid, so if that's genuinely the only thing that will do the job I'll bite the bullet.

Stuff I haven't personally tried, from other questions or sources

Per Resource Scheduling App + Google Calendar:

  • Clippod relies on Google Calendar, and does not appear to have reminder windows.
  • Sunrise Calendar doesn't either.

Per Looking for a software which integrates project management, routines and daily todolist:

  • Asana isn't real clear about what it supports, but it seems to be geared toward team collaboration much more than daily flow.
  • weekplan.net does not appear to have reminder windows and costs $7/mo for recurrence.

From Utilities to manage projects with calendar:

  • Basecamp is $20/mo (!) and appears to rely on email reminders.

*The main obstacle is really the unusually demanding nature of the UX. My skillset is not really centered on designing programs where every millisecond, click, keystroke, and mouse movement counts so heavily. (Line of business apps are ... extremely forgiving in this regard, since you can basically make them out of barbed wire and broken dreams and the users will hardly even ask you to improve anything. Of course, I have much higher standards than that, but there's only so much you can do when the client is unwilling to spend an extra grand on spit and polish.)

  • I found two programs (ticktick.com and conqu.com) that might work while writing this up, but in the interests of a) not losing the work I put into this and b) helping other weirdos with highly specific needs, I'm going to post this anyway and self-answer if either of those turns out good after some time. – Nathan Tuggy Mar 24 '15 at 7:33
  • Todoist doesn't seem to have reminder windows The webapp uses Chrome desktop notifications, though they are pretty simple with only "go to task" and "dismiss" functions – Tymric Mar 24 '15 at 11:53
  • @Timmy: Ah, OK, thanks. I might add that to the list of possibles. – Nathan Tuggy Mar 24 '15 at 13:50
  • 1
    I was just correcting the statement about reminder windows. Todoist still doesn't have all of your requirements, such as detecting overlaps – Tymric Mar 24 '15 at 13:59
  • I havent fully read your question but One Calendar on Windows 8/10 might prove useful – user32882 Sep 22 '15 at 3:42

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