How do I break down and tackle huge projects?
September 2, 2014 2:59 PM   Subscribe

How on earth do adults organize huge projects? And allot time to them? And then actually get them done?

I am completely serious about this. I've always been a horrible procrastinator who does literally anything and everything other than what I'm supposed to be working on for weeks and then goes on a 72-hour hyperfocus hell march to do in one fell swoop what I should have spread out over six months. This has worked okay(ish) up till now but the projects I'm taking on now are self-driven, much higher-stakes, and have a higher potential to go off the rails.

I have a vague idea of how people are supposed to do these things: 1) break project into phases; 2) create a timeline with intermediate deadlines and a budget if needed; 3) map phases into concrete steps with deliverables and dependencies. BUT. I get way too hung up on the planning and making the plan perfect. I am horrible at estimating how much time any given phase will REALLY take. I get distracted by internet cats and laundry and snacks. I blow by intermediate deadlines without a qualm. I edit constantly as I go and usually want to completely restart at least once.

Once I actually get into something it's not a problem to focus and do quality work. But once I'm in it, it's hard to get out of it and the rest of my life goes off the rails while I work feverishly.

Obviously this is not a good way to go about things. I'm better at this stuff in very structured environments and on teams with people relying on me, but I don't know how to do better more consistently when it's just me. I need project and time-management strategies, advice for work-life balance (even when the "work" is something personal), motivation, simple advice like "Don't work on your couch, sit at a desk", whatever you've got!

Other relevant data:
- I've recently started on ADHD meds, which are helping a lot with some of this but also highlighting my need for real systems rather than coping mechanisms.
- I am not overcommitted; I have plenty of time to take on a big project or two a year outside of my day job...if I don't just goof off with all the time I schedule for it.
- Example straightforward but still overwhelming project: Delivering a book manuscript due in six months.
- Example complex and overwhelming project: Planning and creating a content and ecom website for launch in early 2016, which will require consulting with and managing freelancers.
- I've tried Getting Things Done but got so wrapped up in perfecting the administration of the system that I rarely actually did the things. I've tried the Eisenhower Punnett square thing, but everything always seems to be both important and urgent. I tried Pomodoro but I just ignore when the break is up.

TL; DR: I'm the worst at project management and I want to not be the worst. Please help!
posted by peachfuzz to Work & Money (10 answers total) 40 users marked this as a favorite
Hi, I'm you, without ADHD meds, and with different projects. (I promise you are NOT the worst at project management!!)

The big thing I'm focusing on right now: It doesn't have to be flawless, it has to be finished. I want everything I do to be 100% grade A++ level work. But it can't be. Otherwise, I'm not finishing ANYTHING. So I keep reminding myself, it doesn't have to be flawless; it has to be finished. I have that on post-it notes all over my office (aka my living room) and my home.

(That's all I've got.....because I'm you. Seriously. Thanks for this ask!!)
posted by The Almighty Mommy Goddess at 3:15 PM on September 2, 2014 [2 favorites]

What you say about GTD makes me think you might be one of those people – like me! – for whom there's a real risk of getting too caught up in project planning and productivity schemes, in which case, it could be quite easy for this question to become part of the problem instead of the solution. If that sounds right, I think the main thing, at the beginning, is just to make sure you do at least something on the real substantive meat of one of the projects, every day, even if it's just 10 minutes. Make a rule: no more project-planning without at least a little bit of real project-doing.

Also, you could try 90 minute work periods instead of Pomodoro; you're more likely to be naturally tired when the timer goes off, so you might be more likely to get up and take a break.
posted by oliverburkeman at 3:32 PM on September 2, 2014 [1 favorite]

I would turn your thinking around about project vs. time and think about time vs. project. Here's what I mean, and I'm cribbing a bit from Agile/Scrum and some from waterfall, and some just from futzing around with project management in my own sloppy way.

Think about your deadline first. When does this project need to be done? Fantastic, now break that into even chunks. Don't worry about what goes into them yet.

Got that? Great. Now look at your project again. Between now and then end of the first chunk, what could you reasonably expect to be "finished" with by then? I don't mean "perfect," I mean, "minimum viable product" at this point.

Great. That's your unit of measure. You can get that much done in one chunk. Now look at the full project and break that down into the rest of the chunks, knowing that you have to have something "done" by the end of that. Done as in, "I could turn this in, and it would be a project completed on all its own."

Refining your project overall should happen at the end of your midway chunk and the end chunk, so adjust your chunks for that. And then go back and make adjustments to all the other chunks.

This is totally rough and not at all how it should be done, but it can get you thinking about how to approach this. Don't think about the whole project, but how you can cut it up into things you can get done.
posted by xingcat at 3:46 PM on September 2, 2014 [2 favorites]

You have two really common issues: procrastinatory perfectionism and disinterest in arbitrary deadlines. You really have to tackle those issues to be a competent project manager.

Perfectionists hate not being perfect from the first go, but you really cannot master this skill without practice. This is bowling: you can read all the books you want but none of them are going to develop your throwing arm. But a year from now, if you practice, you'll know exactly how to adjust your throw on especially humid days.

Just make a plan, roughly, in a spreadsheet. Figure out how many words a day you need to write, working 4 nights a week, for the next six months. Track your progress. Know that you are going to adjust the plan as you go. Know that when you are done with this project you will know more about making a plan when the next one arrives.

And then as a favor to yourself and Future You, seriously try for the deadlines. Do it in the name of science, as data collection for the next time you do this kind of project.

(Alternately, if this is a possibility, schedule a status meeting with the customer/editor every week and show them your progress. That is how I light an actual fire under my ass: real deadlines, other people.)

I honestly think GTD and the ilk are for slightly advanced users. Right now you need to not let the perfect be the enemy of the good, and get some experience with an extremely simple process before you outgrow it into something more complex.
posted by Lyn Never at 3:56 PM on September 2, 2014 [7 favorites]

2) map phases into concrete steps with deliverables and dependencies. BUT. I get way too hung up on the planning and making the plan perfect. I am horrible at estimating how much time any given phase will REALLY take.

I think this is a formula for disappointment for most humans. There is way too much future predicting in that process. Try this:

1) Figure out which one project you really want to do and want to do even if it goes over time.

2) Figure out deliverables. If you happen to think of dependencies, write them down, but if you don't, don't waste your energy and time trying to Nostradamus them all out. Make the deliverables very, very tiny. Like, a section of a chapter, if we're talking about a book.

3) Do not worry about how much time every phase will take. Just take a stab at what the first few tasks you have to do will take.

4) Start working. Don't worry if you're not doing it perfectly.

5) As soon as you have any deliverable, deliver it to someone you trust and see what they say.

6) Try to figure out if you can cut out the next part, then start working on whatever the next part is after you cull parts. This is important. After each deliverable, figure out what you can do less of and what you can do better.

The important thing is that you are never scared to start the next step and that, except for at the very very beginning, you have something to show someone other than yourself if the project gets cut short. e.g. "Here's the heart of an e-commerce site I'm building. It's missing this, this, and that, but what's there works." Or, "Here's six chapters of the manuscript. I think they're solid and can work as an eBook, but I can expand on it if you think it's worthwhile."

Just do whatever it takes to keep flowing along. Don't spend more time estimating and planning and worrying than you do working.
posted by ignignokt at 4:17 PM on September 2, 2014 [1 favorite]

This is not the best way, but it is a way to build habits:

1. Tackle the step you know you are on for a set number of minutes or hours a day. I hear you about the breaks...I suggest starting as early in the day as possible with a really good reward for actually working during that time. I agree with the 90 minute thing above. Your goal is 90 good minutes of work beginning at precisely 8 am or whatever. If you have someone willing to be your accountability coach for this, that's great. Writers sometimes meet places for a writing date, for example, or you could text someone at the start and end. Do not, however, let accountability checks eat into your predetermined amount of time.

2. Before you stop, write down what you will start with for the next step, leaving that halfway done if possible...for example, stop in the middle of a sentence or paragraph or with half the formatting done on a spreadsheet or one very obvious piece of trim still to miter and a sticky note or red font or whatever (no need to set up a complex system) telling yourself "start with XX" for the next 90-min period/day/whatever.

Once you have this down for a week or two then you can move more to the Agile type bit as listed above. But you have to build the muscles, which are a) butt in seat (or equivalent) and b) a plan for where to _start_ the next time.
posted by warriorqueen at 6:08 PM on September 2, 2014

This is very 101-level, but what works for me is to tell myself I have two choices for where to direct my attention (during the hours I have allocated for working on the project): working on the project, or thinking about why I'm not working on the project.

My attention is going to wander. That's just how my mind is. Whenever I notice myself doing laundry during project time, for example, I stop, and I make a decision: can I just work on the project right now? And if I don't feel like I can just pick up the project where I left off, then I get to sit and think (or better yet, write longhand in a notebook) about why I'm not working on the project. Not about other stuff, just why I think I'm not working.

If I then find myself looking at internet cats, as soon as I realize it, decision time again: could I just go ahead and work on the project? If so, work. If not, back to the notebook and writing down reasons why I'm not working. Pretty soon, I get tired of dwelling on all the reasons why I'm not working, and it seems easier to just work.
posted by Bentobox Humperdinck at 7:27 PM on September 2, 2014

I often struggle with this, especially on the perfectionism part but also on the whole "OH WOW OH WOW THERE'S SO MUCH TO DOOOO" and the three things that keep me grounded are:

1. Frantically drawing on whiteboards
2. My former boss's favorite phrase: "meh, just 80/20 it"
3. Five-minute rule

The first tactic helps me scratch my panic-focus itch. The second one reminds me that "almost" really is good enough for, well, pretty much everybody else on the team.

The last tactic is the kickstart tactic when I start feeling overwhelmed. "Just work on it for 5 minutes." Sometimes you get into flow state within that time, and sometimes you don't. If you don't move on to something else...but you know what actually most of the time you will get into it within 5 minutes. It's a dumb trick and sort of embarrassing how well it works.
posted by Doleful Creature at 10:50 PM on September 2, 2014 [1 favorite]

My biggest barrier is convincing myself that I want to work on it. When I want something done, it gets done, but when I would prefer to look at cats on the internet, things get very hairy.
For me, the purpose of breaking things down into lists of tasks is not so much to organize the project, but to give me something that I want to do: cross an item off the list! Getting a lot done in the 3 hours before a meeting is about wanting to look competent when I know someone is about to be paying attention, so I often set mini-goals involving showing my stuff to other people (eg I'd like to email the other dude on the project with a note telling him what I found out about X, so I'd better finish that analysis by 4:30 or he won't see the note till tomorrow.)
posted by aimedwander at 7:11 AM on September 3, 2014

Response by poster: You guys, I was nervously scoffing at the idea that I was using planning to procrastinate when I realized that of course you are all exactly 100% right.

Some of these tips seem to have been designed for me, especially the ideas to do something for five minutes and to stop with something undone. And of course 80/20. If I'm honest, I usually end up doing 80% of what I know I could do anyway because I'm under such a time crunch; hopefully I can eventually get ahead enough to get a draft done with 80% and come back and revisit to take it further.

odinsdream: Here I'm primarily talking about personal projects; perversely, I am mostly fine in my day job in an extremely deadline-driven industry. I actually hope to develop a mindset that can help me with anything that can be loosely defined as a project—writing this goddamn book, following through with organizations and activities, remodeling a bathroom all might count. I know the specific strategies might be different, but the core solves—too much thinking, not enough doing—are things that I think will be useful across the board.

Anyone have more thoughts on workflow and daily task hacks for being more productive on personal work? Building in checks with third parties is a great idea. Or even really simple things—like, I've noticed that I work a lot better in a cool room and so have been taking myself to air-conditioned coffee shops and libraries during the heat of the summer. Or, I really like being able to see progress on a big flat plan of the project at any time, so I make one in a notebook with post-it tabs of different colors for pieces in planning, draft, proof, and complete.
posted by peachfuzz at 10:08 AM on September 3, 2014

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