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[Vector]

I noticed that I have a chronic problem with having trouble estimating the amount of time something will take, and therefore cannot schedule to save my life.  This leads to a lot of making plans and backing out, whereas previously I simply wouldn't make plans at all and ended up miserable and alone.

How do you guys deal with this issue?  Do you know how I can learn to do a better job of this?

[Truean]

Divide your day into three productive periods:

Morning,
Afternoon,
Evening.

Schedule things in the same location or that are related to one another by subject matter in the same day and productive period. This will give you 15 (5x3) things at least per week if you do a 5 day week or 21 (7x3). That's either 60 or 84 major things you can get done in a month, assuming you only do two things in a production period (a morning or an afternoon or an evening)

If you do 2 things per production period at 3 production periods a day, then that's 6 things a day .... Keep in mind that, of course certain things will be more involved than others and thus require being broken up into parts. This is to be expected, and the trick, as you have pointed out, is deciding where to draw the line. The only thing that can tell you that is experience and asking others how long it takes them to do it (and how long it took them do to it when they were starting out.

This is pretty much the only way I maintain my sanity give off the appearance that I'm not crazy get shit done.

[Mephansteras]

If you want to be organized about it, start making a log of how long various things take you. So, stuff like dishes or laundry or whatnot will have a general block of time that you can count on them taking. For example, I know that doing dishes takes me about an hour. Eventually you'll get a very good sense for how long things take.

Stuff with friends, for the most part, is assumed to take up an entire evening with the possible exception of having dinner beforehand if that's not part of the stuff I'm doing with friends.

Otherwise, I mostly just assume that everything takes about an hour longer than I expect just due to delays, travel time, whatever.

[Lectorog]

If you want to be organized about it, start making a log of how long various things take you.

I think this is the most straightforward way. Most people keep track of this after doing things, consciously or not; if you don't, try a written record and refer to it when planning.

[Max White]

Even when unable to estimate a required time, you can still make a schedule, just with a lesser degree of precision.
The easiest way to schedule is without a time at all, just a series of events that you need to cover. Once one is done you move on to the next. This is impossible in some cases, but easily done in others. Just try to be ready for events with a set time and the rest might come more easily.

You need to be able to roll with what ever happens.

[freeformschooler]

If you want to be organized about it, start making a log of how long various things take you.

I think this is the most straightforward way. Most people keep track of this after doing things, consciously or not; if you don't, try a written record and refer to it when planning.

Yeah, some people can do it in their head. If you drive a lot, for example, you can estimate how long it will take you to get to x place you've driven to a bunch of times before. Not everyone can, though, so a log is a great idea.

[Vector]

Yeah, I have almost no time or spatial sense.  So I'm working on the time thing, because I think that will be easier to change than my sense of space.

I've decided that today I'm working on getting a better idea of my priorities, which will help with some parts of the "sign up for stuff and then cancel" habit.  Then I'll start logging some more common activities.

[Max White]

Can't help you with space... I'm blind in one eye thus no depth perception, so you most likely have an easier time than me.

[Vector]

Nah, I mean that apparently some people have internal compasses or whatever and it takes me about four years in a place to not get lost when I turn around.

[Max White]

What sort of place do you live in?
Cities are easy, the places are full of tall land marks for you to navigate from. Country towns are a little harder due to being composed of the same road copy and pasted over and over.

[Vector]

A university in a city.

I told you, my direction sense is really bad.

[Lectorog]

Land marks don't help if you don't automatically remember them.

[Max White]

A university in a city.

Going to be honest with you here, that is pretty bad. I mean it isn't unheard of, but beyond my area of expertise.

...
Because, you know, I have expertise and all. Any advice I give is pretty much infallible.

[freeformschooler]

No, I totally get it. When I tried to walk to a restaurant called West First a few years back, I didn't put together that it was on First St. The west side of First St. When I did, I asked, "which way is west?"

There's no way to improve that. I memorize directions, paths, connections, but I couldn't spatially tell you how to get from the end of one of those paths to the beginning of another. Time, on the other hand, can be managed when you're not flying through the Interstate at 60 mph and have no idea where you're going.

GPS was built for people like us.

[Mullet Master]

Vector,

Time estimation is difficult for a majority of people. There are many ways to get better at it - I would recommend David Allen's "Getting Things Done" book (You can look up on amazon or your preferred vendor). While you may be a little put off by the 'corporate' exterior, it boils down to being a time management book for everyone.

As far as making plans - here's a few rules of thumb I go by. Your experience may vary, but if you're starting with nothing, this will be a step in a positive direction.

1) Whatever you are doing, if you do it with a single other person, it's going to take twice as long. When in a larger group than that, it's going to take 2.5x as long, minimum. See math? Yuck, I know . But if it takes you one hour to get dinner at some restaurant, getting it with a group of six is likely going to take 2.5 hrs (due to people being late, not being able to get a table, etc.).

2) Starting right now, double your travel time estimates to get anywhere. Most people grossly underestimate travel times. In your case, you've already said you get lost easily ( I do too...) so I think this will be a very positive step for you.

3) Since you are in university, schedule studying in 3 hour blocks. You'll never really get anything done in shorter blocks- really they should be longer but I realise that's very hard to do sometimes.

4) If you are going out - to a bar, club, etc, always assume that it will take the rest of the night, no matter what time you start. Do not try to make plans with more than one group of people, unless everyone from both groups has agreed to meet at a set time/location.