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Developing time management skills?

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galliver:
In a nutshell: I'm looking for strategies to use to improve my ability to predict how long tasks will take and schedule them accordingly. I expected this to be one of the life skills I'd pick up intuitively with time/as it was needed but it hasn't really happened so I want to take some proactive steps!

I definitely have a perfectly serviceable grasp of it for everyday life; I generally make appointments, meetings, planes, etc on time; when I was taking classes I generally met deadlines; if I'm in a scheduled environment (like a conference) or I make plans with a friend (e.g. meet up to go hiking at X time) I will get to where I need or want or promised to be (even if there's no external accountability but just a one-time event that can't be moved, like attending a talk). I DO have trouble scheduling work tasks or personal projects or (on weekends, esp) chores when I am only accountable to myself and things are pretty flexible and can be adapted if I start late or take too long or get distracted.

More on me: I'd say I'm a 7/10 on the organization scale. I have places for my important papers, I keep like items together, I like small objects put away/sorted in other boxes/containers if possible, I fold my clothes. I do have some clutter/mess tolerance and have been known to leave out/forget things I was using, but eventually go through and put them away. I've low tolerance of dirt (floor spots, dust bunnies). I have topical folders on my computer and Dropbox. In college I had the intuition to keep close tabs on the balance in my bank account; in grad school I started using Mint to help categorize a larger set of expenses. I do admit that although I keep some budgets in there, I tend more toward the "critically evaluate every purchase" mentality. I don't really care if I go $20 over my aspirational grocery budget, or if I decide 3 weeks into the month to buy tickets to go see my family (of course, subject to still being in the black/hitting minimum savings goals!). I'm definitely not as extreme as MMM about what constitutes need/reasonable want (I own TWO mops O: )

I am a recovering procrastinator and (I think this is related) recovering perfectionist. I've been doing much better at both as I've gone through grad school (engineering; due to defend my PhD within a few months), but sometimes the old habits do still rear their ugly heads. Also a night owl by nature (even if I got up early and was a zombie all day, I'll actually wake up *more* between 8-11pm or later); my preferred sleep starts between 11pm-3am and goes for 8-9hrs.

More specific sub-questions:
1) How to maintain a positive outlook/attitude about this or set up a reward system? Previous attempts to better manage time have usually resulted in self-shaming and subsequently giving up when things didn't go perfectly (see: perfectionist tendencies!).
2) How to anticipate time/effort required in tasks that are more open-ended? I know, at least roughly, how long it takes to wash dishes but I wouldn't know how long it would take to e.g. fix my vacuum cleaner (if it broke) or write a code that does XYZ? Or, even for tasks I basically know the timing of, I have a hard time remembering to account for setup/cleanup/transition/distraction/traffic types of things.
2b) Follow up on above: I often find myself chaining tasks together...like when cleaning, washing dishes will lead to sweeping/vacuuming the kitchen, then the whole apartment, then mopping, then bathroom, even if I didn't necessarily start out with a plan to clean EVERYTHING. Or I'll write that XYZ code and then realize I could also write an addendum to do A, then B, etc etc and if I don't get stumped by something hard enough to lose momentum, I find it difficult to stop, reprioritize, and redirect.
3) How to plan and/or adapt to energy ebb and flow? (Different tasks are better suited to different degrees of alertness, which varies day-to-day and throughout the day for most people. It can be hard to anticipate feeling different than one does in the moment.)
4) Taking breaks. I think it would be great for my health and possibly focus to stand up, walk around, get water, etc but since I know I have a difficulty starting I tend to hesitate to take breaks once I'm working on a task...and if I do they tend to stretch out to be longer than I actually meant (see 2b haha).

Looking forward to MMM community's advice, sympathy/commisseration/"to follow" comments from those also working on this also appreciated! ;)

galliver:
Shameless self-bump! I was hoping for more, but I expect people went off to enjoy their weekend :)

In the absence of external advice, I did two things...picked up a planner like the ones I used in high school, in case that was helping me stay more organized more than the deadlines were, and downloaded a Pomodoro method app (this one also has a timesheet function so I can see the total time I spent on things in a particular day). Remains to be seen if I'll stick with these long term, but my time does feel more structured...or at least structurable.

Would still love to hear about others' experiences and tips though.

Cali Nonya:
From someone who was once a super-doer, and has become just a run of the mill normal person.  I can sort of opine about some of the causes.

What you are describing isn't lack of time management skills, but more along the lines of motivation to get started.  Those are two very different things.  I would say, on the weekend, if you find yourself not getting started on something, what exactly are you doing?  I know for me, it's mindless internet browsing or reading.  I know exactly where this habit come from (down time on a job that required a TON of travel).  But habit loops are hard to break.

What has worked for me, and I might actually try soon again is: Lists.  For me, it's helpful to have a list of To-Do's on the fridge, and mostly fairly generic to-do's.  So if you are aimless, you can start on an easy one (and quite often all that is needed is to be moving and start something in order to get going).  Make sure the list includes repetitive things (like yard work, de-cluttering, etc,) and larger projects you want done.  The list is just a prompt to break the inertia habit.

Noodle:
So your issue is that you get caught up in a project and it causes you to be delayed with or miss other things on your agenda for the day?

Perhaps it would help to expect that some projects are multisession and to set an alarm for yourself when you need to move on to other projects. You could even have two alarms...one for five minutes before you have to stop to give you time to jot down notes about where you are, pick up your tools, schedule your next session etc. It sounds like one of your issues might be that you don't feel confident that you can pick up a project again seamlessly. The "Getting Things Done" method (it's a book) is pretty effective about capturing information.

Or schedule all the time-sensitive must-dos of your day first and then you can dive as deep as you want into your less-defined projects.

caracarn:
I would agree that your post sounds like lack of motivation.  You arrive on time to things you must, and get to meetings.  You did not address if you have this problem in your work task list as well.  Everything you listed is personal items.

The only solution I have ever found is to realize that if you are not motivated then whatever it is that you leave undone is not reaching some threshold of importance to you.  You indicated that in some case you are self-shaming or you need accountability, but if you did not do it and then make yourself feel bad, I'd still say that simply means that the "threat" of making yourself feel bad (which I assume you are aware will happen unless you have some strange mental disorder you left out) is just validating that "pain" is more palatable than doing the task you did not do, i.e. it's not important to you.  Having external pressure does not change the importance level internally.

One of my larger roles at work is project manager so I am constantly keeping myself and others on task.  But for personal tasks, there are certainly times when I do not do something I was planning on doing, and it always can be traced back to it just was not as important and what I chose to do instead.  If you have ever used YNAB for budgeting (and your mentality that you described sounds like it would be a much better fit for your budgeting than Mint is) it is similar when you decide what jobs your dollars will do.  You can take that mentality to your personal task list and realize that is what you are doing each time you make a choice to do x instead of y, or keep doing x instead of y, which comes right back to importance.  So I'd suggest figuring out either how to make what you say you want to do more important to you so you are motivated to do it or realize that the things you are not doing are not that important to you, make peace with that, stop beating yourself up about them and focus on filling your to-do list with things that are actually important enough to you to get done.

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