Listmaker, listmaker, make me a list...
September 11, 2012 7:15 PM   Subscribe

To-do questions on here often tell you to have a daily or weekly meeting with your boss. Please help me figure out how to make a list of tasks and projects so that I can do this and keep my head on straight and not get mired in anxiety-land.

I am using my sockpuppet for this cause my real name is attached my main account and I am embarrassed by even asking this.

I have anxiety so I know that doesn't help. I'm in therapy, on meds, etc. I may have some mild ADHD but the docs think my issues are more based on anxiety.

Anyways, to the issue at hand...

First off, my boss thinks I'm doing fine. He just doesn't have the same issues with organization and follow through and anxiety about it all that I do. I just want to do a good job and feel like I'm on top of things. I feel like I'm just wading through, doing this, doing that and barely staying on top.

I've tried numerous task organizers and project management apps over the years but I can't wrap my head about how to actually use them. I eventually get overwhelmed by the amount of tasks and no longer can see what I need to do. What happens is that a project will start, it turns into something incredibly complex when I thought it was simple and all sorts of unexpected things happen and I got lost because the plan changed and I no longer feel like I know what's going on.

I don't know how to keep track of various tasks that "in progress" - maybe it's because I need someone's help or I'm waiting on someone else to do something so I can go finish it or just that I got stuck and need to think about it for a little.

I need to juggle like 18 chainsaws and cats without hurting anyone. I just don't know how to organize that.

I feel like the task list I have and the task list I would discuss with my boss are really two different lists, the second being more specific. "Create article for the user documentation on Topic A" is actually take screenshots, resize screenshots, put in document and add text. Sometimes I need to tell him that is my plan and other times not...there have been plenty of times that I thought I knew what I needed to do, but turns out there was some other way to do things that would have saved me a lot of time and energy if I had told him what my plan was. But I can't tell him the details of every little thing I'm going to do, it would take too much time.

Also, if I'm working on Task A and then I run into a roadblock that prevents me completing Task A and getting this roadblock cleared means I now have to do several new tasks which are going to take more time than I thought Task A was originally going to take...I lose my shit. I get very stressed. I feel like I'm letting everyone down, the client, my coworkers.

I feel like I have somehow failed to see what I needed to do. That I didn't think things through and didn't make a plan. Cause I didn't. Because I feel like I don't have time to make a plan and when I try to make a plan, I don't know which parts to share with my boss because he doesn't have an hour everyday to go over everything with me - I need that hour he does have to help me actively get things done, like fix problems so I can keep working, not help me refine my todo list.

Another thing ... some times I get very caught up in the trees and can't see the forest. I spent at least an hour and a half trying to find the "right" screencap tool - that was free, that would let me crop and resize, and put little arrows on it. I thought I should do that because this documentation project is going to be something I'm spending a lot time doing. It never occurred to me that my boss might pay $40 for SnagIt because I think it would do the job. (I used SnagIt at my old job so I already knew it was great.)

But maybe that's a different question.

It's late and maybe this was rambly, but I'm just very stressed at work and I do love it, I just really want to feel like I know what's going on and not just randomly putting out fires. All of my jobs end up being this way and I guess it's because I actually do get stuff done and get it done right, but I hate feeling like I have no idea what's going on. I don't want to be a firewoman. Whatever the opposite is, I want to be that.
posted by inmyhead to Work & Money (12 answers total) 9 users marked this as a favorite
This only applies to one little part of your question :

My job is 85% doing the same tasks everyday. I have a checklist of those, which I update periodically. The only time I personally use that list is if a new daily task is added, and I need to fit it into my routine. If I dont do this, it takes me a lot longer to build the habit. The other time this checklist gets used is when someone covers for me.

For the other 15% of projects/favors/fixes/weekly or monthly things, etc I have a board that is divided into 'To Do' , 'In Process', and 'Done'. I jot little notes on Post-Its when I get a task, or have an idea for a project, and stick them in the 'To Do' section. If I'm working on it, it gets moved to the middle 'in process' part , and then to the 'done', when completed.

At the end of each day, I toss the notes in the completed section, and review the other two.

After going thru many, many iterations of task lists, Standard Procedures, prioritizing, etc this has worked best for me. It's a nice visual and physical way to track progress, and see what's on your plate.

If you want, I can memail you a pic of my board, just let me know.
posted by Fig at 7:53 PM on September 11, 2012 [1 favorite]

Best answer: I can't help too much with the multi-tasking juggling cats and chainsaws, because I don't think I'm all that good at it either. What has worked at least alright for me is just to keep a list of the bigger tasks and add subheadings to it as I go along and things grow (usually in excel). But one thing that stuck out from your question for me is that it seems like some of the things you are uncertain about (how to break big tasks into components, which tools to use, etc.) could be derived by understanding how long your boss expects things to take. Are you receiving some guidance on this? I try to let my group know how long a task should take them, with the understanding that if they are not seeing themselves progress at that rate, they should check in with me asap and we can discuss their strategy. If things take about the same amount of time as I would expect, then their strategy is probably just as good as anything I would come up with (I also encourage them to check out how others are doing similar tasks because I know that I am actually probably not the most skilled at doing a lot of the things they do...maybe this would help you to 'know' when you should just buy something or when the general culture would expect you to make do with something freely available.). Likewise, if they are finishing superfast, then maybe they are not doing things to the correct scope (i.e., too shallow).

also, if you knew your boss wasn't going to be shocked that something could take you all day to wade thru, you might be less anxious by the time taken up by unexpected things. as you say, you have generally been successful, so it's unlikely that all those 'delays' are actually caused by you being slow.

If your boss is not giving you this sort of framework on time expectations, you might let him/her know how long things are taking, as a general small part of all the info ("this document came together really easily. i spent an hour on it; let me know if there's anything you'd like me to cover in more detail/if there's anything you think i might have saved time on [dependent on how you feel about it]." "this document was a challenge for me [no need to embellish that you spent 10 times as long as you think you should have, but honestly, i'd want to know that from my group -- i think this sort of info-providing depends on your boss]. i got stuck on the [complicated thing that spun out of control and i don't even know how]. are there any tricks you have for this sort of task?" hopefully, some feedback from you like this would at least get discussion flowing regarding efficiency.
posted by Tandem Affinity at 8:24 PM on September 11, 2012

Response by poster: Tandem Affinity - i think you hit the nail on the head. I needed a metric and didnt know what it was. I think that will help immensely to ask about target times. He and i have talked about estimating time before and he said it was hard for him at first too.

Fig - my job is reversed. 90% is not the same day to day or even project to project.

Im going to sleep now. I definitely feel better now that at least part of this is cleared up w/ the asking about time expectations.
posted by inmyhead at 8:32 PM on September 11, 2012

Response by poster: One more clarification... We're a really small company of 5 people. No one else does the work i do except my boss so theres no one else to ask for help or to see how they do things.
posted by inmyhead at 8:34 PM on September 11, 2012

I have a job that seems a little bit like yours - firefighting is what I do, and no two weeks are ever the same. And this is my first management position, and I have struggled a lot. My boss (who is excruciatingly detail-oriented though not a micromanager thank all deities) did biweekly meetings from the get-go, and eventually I kind of had to point at him and say, "Dude, I need a mentor. You're it. Help me know what I need to know."

And he totally jumped in. We're just very different personalities and while I bring my own useful things to the table, I needed to help him understand how to talk to/help me with all the things he's good at. I am learning the value of overcommunication from him, to the point that I'm thinking about setting up a 15-minute meeting on our off weeks.

Learning to estimate effort is not easy. Everybody knows that. So don't be afraid to ask this person to help you learn to be better at it.
posted by Lyn Never at 8:44 PM on September 11, 2012

If you aren't familiar with it, you might pick up "The seven habits of highly effective people". See if that gives a better handle on some of this stuff.

You also might hit the library and peruse some time management/ project planning type stuff. I did that a long time ago. The main thing that really stuck with me was start with your end date and goal and work backwards from there: What needs to happen before z? And what needs to happen before y? And so on.
posted by Michele in California at 8:56 PM on September 11, 2012

Not sure this is a helpful comment or not. But I once wrote a question similar to this. It turned out that once my workload was more manageable, I stopped overthinking how I structured my "to do" list. Is the fundamental root of the anxiety, etc., here that you have more to do than you can realistically get done?
posted by salvia at 9:37 PM on September 11, 2012 [2 favorites]

Best answer: I asked a similar question a little over two years ago. Though the suggestions people offered were great, it was most helpful to learn the following over that time:

You are very, very normal. This gets better with time.
Juggling multiple tasks is hard. The right way to do a task is often not clear until after you've done it... about 82 times. People often believe a task or project will take less time than it ends up taking -- sometimes because of a mis-estimate, sometimes because of not having all the information, and quite often because something unexpected occurs. I've met few people who simply "know" how to organize and prioritize their work, and of those all had been practicing for some time.

Here's the hardest thing for me to accept to this day:
I've been working so, so hard these last few years to be better -- to stop forgetting appointments, to pay more attention to detail in the right places (and less in the wrong places), to plan my work in advance, to accurately estimate the time I will spend on something -- that when I miss it makes me feel miserable. But I try to remember that
I am so much better at these things now than I was when I started asking myself the question you are asking now.
posted by jander03 at 11:28 PM on September 11, 2012 [3 favorites]

Walk in with three bullet points that you want to ask your boss about, or inform your boss about. It doesn't have to be everything you want to talk about, just three items for that particular meeting. Ideally they fall into the category of "I was wondering if" or "I have some good news about project x", because anything you needed their help to unblock/bad stuff they needed to know about, you already shared that in the moment you needed it/discovered it.

If your boss wants to know something that isn't on your list, they'll ask.
posted by davejay at 11:40 PM on September 11, 2012

Best answer: What helped me to organise and manage large numbers of tasks and projects was using Getting Things Done. Not for everyone, but worth reading if you haven't already.

In terms of managing my own anxieties about doing this kind of job - you have to remember that this kind of firefighting role can't be done perfectly. You have to accept a certain amount of planning fail as normal, rather than as a sign that you are doing a bad job. It sounds like you are consciously trying to get better, and your boss is happy, so give yourself some credit.
posted by crocomancer at 2:10 AM on September 12, 2012

Response by poster: thanks everyone!

this makes me a feel a lot better. i do have more than realistically can be done and i just want to do it all and do it all right. i probably do not give myself enough credit (guess i can talk about that in therapy!). so many of you saying that i need to see that and that this is par for course really helps.

w/r/t the bullet points davejay makes - my "meetings" aren't necessarily meetings. they're when my boss has some down time that he can come help me with stuff. i can't let him know "in the moment" that i discovered i needed something. i have to make a list of what i need his help on and hope he has enough time to help me figure that out. i guess that's also part of the frustration is that i never feel i get through my list and that the path from here to the goal is so murky. i'm not the world's best planner, but i do like to have an idea and i often feel like i have no idea whatsoever because the idea i did have turns out to be very different from what actually is happneing.

maybe i should ask him for dedicated time each time day or every other day - like a mon/wed/fri meeting of 15-30 where we can just review whatever and i know that i 'll have time?

as i was typing this i realized that not knowing WHEN he'll have time is also driving a lot of anxiety about this.
posted by inmyhead at 7:08 AM on September 12, 2012

Also, if I'm working on Task A and then I run into a roadblock that prevents me completing Task A and getting this roadblock cleared means I now have to do several new tasks which are going to take more time than I thought Task A was originally going to take...I lose my shit. I get very stressed. I feel like I'm letting everyone down, the client, my coworkers.

Perhaps you're in a different field than I am, but for me (a programmer) virtually every single task I do has a 10%+ change of taking 3-4 times longer than I anticipated. It's frustrating when it happens, but I don't blame myself because I generally could not have anticipated the problem and pretty much everybody I work with understands that this is going to happen with some regularity.

One adjustment I have made is to always double my estimates for how long tasks will take. This is actually a standard practice in software engineering and it allows for wiggle room for those inevitable tasks that end up taking much longer than anticipated.

Hofstadter's Law: Any computing project will take twice as long as you think it will — even when you take into account Hofstadter's Law.
posted by callmejay at 8:57 AM on September 12, 2012

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