Developing time management skills?

[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.

[jaykim0505]

to start developing the time management skills, first you should kill laziness and reinforce the strength of will. your ideas are good, indeed, thanks for sharing

[Linea_Norway]

I use a light-version of the "getting things done" method. I have an app where I can put in my tasks/projects, big and small, everything I can think of for any context. The app is synchronized on my phone, iPad and PCs. Inside the app I can organize the tasks by context, by projects and by when they need to get done. Some have a specific deadline and pop up in "today". Then I just do them. Others are in the "next" list and I look in it sometimes when I have left-over time. I review the tasks sometimes, but not as often as I perhaps should do. During reviewing, is you see a tasks that will take less than 2 minutes, you should just do it immediately. You can also choose to reschedule the task. My app is called i.DoIt.im and I pay for the synchronized version.

What you say about chaining tasks, sounds very familiar. When I am doing a chore and I notice something else that needs to be done (dirts on the floor or so), I do that other thing directly afterwards, and the next thing and the next thing. There is always a lot to be noticed. I experience this as stressful. It is a way of making yourself feel hyper effective and useful, but is very stressful, probably also for your surroundings. Maybe it is better to focus more to the task being done and not trying to look around for other things to be done. And if they are there, then write it on the todo list and do it some other time.

When it comes to scheduling time. You mentioned transportation. Can't you use some road finding app that can give you a clue at how long it takes to get somewhere? Otherwise, you could perhaps use something like we do in software development (SCRUM-method). We don't schedule in time, but we schedule task sizes in comparison to each other. You could for example use for your tasks:

• a few minutes
• an hour
• half a day
• a whole day
• several days
• a big project

Would that help? I think it could also help for you to write down all the tasks you want to perform on a certain day and check them off one by one. Maybe that will help you to check them off before you start doing the next, unscheduled thing in chain.

[whatupjeffy]

I'm just using a time management app on my cellphone and quite satisfied with my time management, especially good for those, who's always late, cuz it's really annoying (know some representatives of such a group)

[galliver]

Thanks for your input and suggestions everyone! I'm going to answer some of the points raised thematically rather than post-by-post (for efficiency ;) )

- Motivation is definitely a factor related to time management, and also a very complicated issue that's tied in to a lot of different things. Heck, something as simple as sleep--seemed like this past week every other night I was only getting 4-6 hrs of poor, interrupted sleep and my focus and motivation was tanking. But also stuff like pleasurability/satisfaction vs "ugh factor" of an activity (obviously), or confidence vs fear/anxiety about it, those kinds of things. In addition, of course, to its perceived importance.
- Intrinsic vs extrinsic motivation. I feel like these are sometimes used as extremes on a very polarized scale: intrinsic-good, extrinsic-bad. But I think that while some people are driven to pursue their own ideas, ventures, etc, others are intrinsically driven to help/serve others and that's a good thing (you can't make a team where everyone just wants to do Their Thing). I think I belong to the latter group; it's not that I'm not driven if I don't have a stick over my head, it's that I want/need to know someone else will benefit from my work, or needs it, or expects it.
- I love To Do lists! However, they tend to result in some important, non-urgent, unpleasant task constantly falling to the bottom. I find them particularly great for something like planning for a trip, where tasks actually disappear once completed...it's far less satisfying when there's just a few tasks in a day, and possibly one task goes on for several days (e.g. if I have to process data from 100 tests, I either have "process data" as a task for 5 days straight, or "process 1-20" gets replaced by "process 21-40" which isn't much more satisfying...) I do also like them for prioritizing long-term, like when I finish a big task and know I have a couple others and am not sure what to start on; writing them out can help articulate the parameters of the tasks and pick the most important one. Maybe I should make it a habit to do this kind of prioritizing more often/regularly, but it doesn't seem like something that'll work great day-to-day, at least where I am now.
- Incidentally, although as a 21st century human I do get distracted from what I think I should be doing by stuff online, I also have a tendency to get sidetracked into cleaning and cooking. Not-unimportant, satisfying (sometimes pleasant), tasks that I'm good at. But ultimately not the most important thing I could be working on. (And obviously, there's a minimal degree of hygiene and nutrition to uphold, and then there's optional aspects of both these tasks. Sometimes it's hard to decide if making-that-thing-I-want is "worth it").
- I really like the idea of simply categorizing the anticipated time sink of a task (minutes, hour, half-day, full-day, N days). Except it might be I need to go up one for my estimates, since one thing that tanks my to-do lists is excessive optimism.
- Willpower vs laziness. Absolutely true, though I would hate to go through life just forcing myself to do things and hating it rather than getting enthused. It's like...if you just approach frugality through deprivation rather than through enjoying simple pleasures and the "cha ching" instinct when you put money away. I'm looking to get better at structuring my minutes similar to how I do my dollars, except the former comes less naturally to me.

One of my larger roles at work is project manager so I am constantly keeping myself and others on task.

caracarn, I'd be really curious to hear more from you from a professional project management perspective... If it's part of your role (either alone or collectively with coworkers), how do you lay out the plan for a long-term project (I presume you're dealing with multi-month or multi-year, multi-person projects). How do you decide what "on task" or "on track" is? And then how do you deal with it when things start going off-track for any reason (obviously there's stuff like outages, delays backorders, medical issues, etc happen as well as people not performing up to their potential/expectations...but either way the projects end up set back)? How do you curb excessive optimism about what is possible?

Thanks again everybody!

[Linea_Norway]

caracarn, I'd be really curious to hear more from you from a professional project management perspective... If it's part of your role (either alone or collectively with coworkers), how do you lay out the plan for a long-term project (I presume you're dealing with multi-month or multi-year, multi-person projects). How do you decide what "on task" or "on track" is? And then how do you deal with it when things start going off-track for any reason (obviously there's stuff like outages, delays backorders, medical issues, etc happen as well as people not performing up to their potential/expectations...but either way the projects end up set back)? How do you curb excessive optimism about what is possible?

One idea to check whether everyone is on track is making an estimate (e.g. number of hours that a task would last). And then letting people register how many hours are left to do. Then you can make a "burndown" chart, which you can extrapolate to see when a task will be done.
One other thing is to divide big tasks/projects into small tasks that you can actually check off. You can seldom check off a really big task. But if you have many one hour or one day tasks, you can make progress by checking them off one by one.

[GuitarStv]

Generally I find that most things (even things I've been dreading doing) are enjoyable if you're in the right mindset.  The key then to avoid procrastination is simply to find the pluck to actually start doing whatever it is that needs to be done.

[caracarn]

One of my larger roles at work is project manager so I am constantly keeping myself and others on task.

caracarn, I'd be really curious to hear more from you from a professional project management perspective... If it's part of your role (either alone or collectively with coworkers), how do you lay out the plan for a long-term project (I presume you're dealing with multi-month or multi-year, multi-person projects). How do you decide what "on task" or "on track" is? And then how do you deal with it when things start going off-track for any reason (obviously there's stuff like outages, delays backorders, medical issues, etc happen as well as people not performing up to their potential/expectations...but either way the projects end up set back)? How do you curb excessive optimism about what is possible?

Thanks again everybody!

I am so sorry I did not see this until now.  Hopefully @galliver will see the response.

Yes, I work on long projects in the IT space, think system implementations as being some of the most involved, ERP and CRM systems mainly, but also new buildings and infrastructure involved. 

I have done these types of projects for a long time so I know the main milestones well and can draft a list of main steps pretty easily.  In project management you do what is called "progressively elaborate" the schedule, meaning as you learn more you add more detail as needed.  I also tend you use what are called agile methods, as opposed to waterfall.  Agile has you develop the plan only for the next few weeks or so and leave the rest very general, where waterfall is the traditional process where you lay everything out in detail over the entire life span.  The wasted effort there is that things change so frequently that you are spending almost all your time updating later stages of the plan, only to have to redo them dozens or hundreds of times over the life of the project.  If you just focus on the immediate items and have place holders for large milestones beyond that, the change is more manageable.

There are ways to actually measure called earned value calculations that will allow you to easily see if you are ahead or behind.  As things go off track you work to find ways to catch up (called crashing the schedule), because in many cases you can find other ways to do things, but sometimes hard choices need to be made.  There is a triple constraints model used that deals with time, scope and cost.  You can have two of the three but never all three, so if time is impacted you have to adjust with scope (taking things out) or cost. 

Managing expectations is a key part of the job.  Contrary to what most people think, a good project manager spends 90% of their job communicating.  It it not about playing with project plans.  That's a very small part of the job.  A key rule I always teach new project managers is your main focus is to never have your stakeholders surprised.  That means you have to get good at delivering bad news no matter how painful.  New project managers try to fix things and do not communicate the true status, hiding the reality.  Sometimes that works.  Most times it fails and fails badly.  That's when people get fired. 

Hope that helps.  I can go on forever on any of these topics so let me know how else I can help.

[galliver]

@caracarn  I did see it. Thanks! Lots of words/concepts for me to Google :)

[golden1]

I separate my tasks into things I have to do everyday (routines) and things that shift and change.  I also have some longer term projects.

In terms of motivation, I have recently gotten into writing sub check lists that chop a bigger task into small, manageable sub tasks. 

My personal favorite to do app is Things3.  I do wish I could assign times to things.  Years ago they used to make an app/program called Memento that allowed you to make a to do and drag and drop it to your calendar and assign a duration.  It was fantastic but they stopped supporting it for some reason.