One more thing on Digital Organizing…a question.

by Elizabeth on September 21, 2012

I always seem to put off the hardest parts ’til last.

I don’t mean to.  I mean to be one of those highly-effective people who picks the hardest thing off the to-do list and do it first thing in the morning, because that’s what all the “experts” tell you is the best thing to do.

The problem, of course, is that when I get up, my head is full of sand and zombielike coffee cravings.  And that’s all.

I have a good hour where I just putter and stare blankly, and on a good day, I might even make the bed.  On a really good day, I might even answer an email.  An, as in singular.

I’ve tried other things, but the fact of the matter is that, in reality, I’m kind of useless first thing in the morning.  I’m perky, I’m semi-awake, I’m always happy…but effective, I am not.

So the hard stuff tends to wait until I’ve got sufficient sand-removal from the brainmeats before I start it.

Generally, this works out okay.  I do better work, instead of just working to be moving.  I send people emails that actually make sense.  And I’ve got the presence of mind to remember not to push red, shiny, candylike buttons that break technological things I might be working on at the time.  (The same is not true for first-thing-in-the-morning or late-at-night working.  I can break very simple things at fifty feet.)

Which is probably why the to-do lists came last this week.

I had to clear out all the rest of the digital sand before I could really focus on how to make things easier for myself when it comes to actual action-taking.  I know.  That sounds counterproductive.  But when you’ve got multiple irons in multiple fires, the ad hoc organization/task system that kind of organically develops over time can feel pretty darn overwhelming to change  – even when you know that something more easily accessed would make things a bazillion times easier to actually do.

See why I left the hard stuff for last now?

Right now, as I mentioned before, I think, I use workflowy for “capture”.

And for this, it’s flippin’ awesome.  It’s structured like a great big outline, in one long list of every kind of thing imaginable.  It’s pretty close to how my brain works, too, which is why it’s been so effective for me in the past.  I’ve got everything from stream of consciousness ideas (which is more like a raging, torrential river, really.) to action items, all in one place, alongside resources and such.  If it’s got a firm deadline, the deadline goes in my iCal.

The problem is that the more prolific the ideas or projects, the less easy it is to find what I need.

My workflowy list, right now, reads like War & Peace … only longer and more ponderous.  I love it.  I continue to use it.  It’s still the best thing for getting ideas out of my head and onto digital “paper”.  But hooboy…is it ever not easy to find specific things, unless I skim the whole list.  (Or at least the list of top-level topics.)

I used to use a Mac-specific task program called “Things”, by the way.

I loved that I could add to-do-list items with a keyboard shortcut from anywhere, which helped with the had-an-idea-but-forgot-it thing.  But a) it was expensive, and had frequent updates for the iPhone app and desktop bits, and b) never sync’ed all that easily.  So to get things off the mobile app, I had to do these weird rain-dances and appeal to the God of Technology with a PC sacrifice at dawn on the full moon, and even then, he was a tempermental snot sometimes.  And if something’s not easy, I won’t keep up with it, plain and simple.

So I tried other things.

I tried rememberthemilk.  I tried tasklist and wunderlist and wordpress plugins and website apps and other paid apps/programs.  I gave up on digital and tried using notebooks:  GTD systems and an interesting list-type thing called Autofocus.  (Which, by the way, is the most like workflowy, and is a good place to start if you’re more pen-and-ink than mouse-and-screen.)

At this point, I probably have fifteengazillion orphaned to-do-lists all over the internet.  Most filled with stuff I’ve either done or don’t care about anymore, in fact.  It’s kind of sad.  Poor motherless action items.

For work, though, I settled on Trello, and I’ll tell you why:

1.  You can make it as simple (leaving the to-do/doing/done boards as-is) or as complex as you want, adding more boards for other things.  (I often add a “someday” board, with things I’d like to do if there’s time/energy/interest.)

2.  It can be collaborative, on a board-by-board basis — you just invite collaborators to the board.  (For those like me, with seventythousandmillion diverse clients, it’s a godsend feature.)

3.  It’s multi-media (you can add photos or files for specific things), and you can color-code, for things like priority.  (It’s a good visual reminder that yes, the content-writing is more important than tweaking a theme, for example.)

If you’re a programmer or something project-managey, OpenProj is probably a better choice, by the way.  There are no milestones or anything to measure things.  Just lists with “cards” for each task, like a pinboard.  It’s good for us creative folks.

So now, I think I want Trello to be not just for work.

My personal projects are copious.  Probably from my preternatural fear of being bored.

Psychology/neurosis aside, I think this might be a good system to keep track of the to-dos for each of those, since it’s so easy to visualize what’s done and what’s not — and what’s important and what’s not.

Here’s my issue:  I have no idea how to organize it.

Do I put in a board for each sub-project, since they all have their own to-dos?  Or just a board for each main project, and have cards for each sub-thing in that overarching project?  And if it’s the former, will that just be digital clutter again in six months, if I decide not to go in that direction?  Or will it choke each board with sub-project to-dos if I go with the latter?

It’s making my head feel all spinny.

do know that leaving it all unorganized on a giant list (workflowy) isn’t working.  Even when my computer screams at me that it’s time to do something for XYZ Project (thank you, Goal Reminder! extension for Chrome), it takes me the better part of a few wasted minutes to scan the whole list and see what, if anything, needs to be done.  And for someone like myself, who tends to be crazy-ADD with the attention-span, sometimes it means I wander off for pie and forget to do anything at all by the time I’ve gone through part of the ponderous list.

Let me just say, too:  I hate being disorganized.

Like, HATE it, hate it.  Like, smack-my-head-on-the-nearest-wall hate it.  It’s one thing to have some kind of technical issue, or to run up against unforseen complications (which happens), or to make a conscious choice not to do something in favor of something more productive.  Those things happen.  But it’s another thing altogether to not get something done because I forgot about it or because I didn’t effectively store the item until I had the time to work on it.  I hate that.

Can you see why I put this off until last?  It’s crazymaking.

So my question for you is this:

How do you keep everything straight?  If you have multiple projects of endeavors going on at once, I really want to hear from you.  If you’ve got insight into the best way to organize the trello pinboards, I’m all for listening to your genius opinions.  How do you keep from forgetting things?  Am I overcomplicating this, as I’m wont to do sometimes, and should I just find a simpler solution?

I’ll say this:  things almost always have to be visible for me to remember them.  If it’s not open, sometimes I forget things exist.  Perils of Ooh Shiny Syndrome.  So having things in one place is preferable to multiple places, and the less organization that’s needed to stay, well, organized, the better.

Gimme your wisdom, people.

I can use all the help I can get in shaking this brainsand out of my head.

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{ 3 comments… read them below or add one }

Darren September 21, 2012 at 9:48 pm

Oh we do seem to have travelled a similar productivity road. Of everything I do I think the autofocus method, offered the best approach. However, I never could stick with it. And that seems like the issue you are facing too. There are plenty of good ideas, but we end up with lists everywhere. Having said all that, I am now using trello too… see what I mean about same road.

Currently I am using it for my music and songs. Each song has its own card that is dragged around as I do more to it. So, for me, I am using one pinboard for each ‘area’ of interest, but each card is a sep project (in true GTD terms). Not sure how long I will stick with it, and I think ‘that’ is my ultimate issue. Which is why the autofocus list still appeals to me. One long list, of actions, in one place :) This is quite interesting on trello


Elizabeth September 21, 2012 at 10:21 pm

That article is *awesome*. I like how he’s got a board for all the goal-y type stuff and future ideas — that’s kind of what I do with workflowy right now. (If it’s out of my head, it’s not competing for attention, and I *love* having all of that in one place so that when one project is completed, I can just pick one that’s screaming the loudest on the braindump list.)

I think my biggest fear with using Trello for all of this is that it’ll dilute actual client work. I’ve been keeping external clients to around five a month (and a few on the waiting list) to keep from going without sleep for long periods of time — but if I get too many boards with personal projects, I’m a little worried that subconsciously, they’ll all take on the same “weight”, so to speak. If there’s one thing I’m not willing to do, it’s not give work the attention it demands, y’know? (Again, the perils of being really visual.)

I *do* like that there are checklists available (hadn’t noticed that so far), so maybe the one-card-per-subproject-one-board-per-project thing is the best way to go. You say that’s working well for you?

(Since we’re productivity twinkies and all….) :D


Jason Hurley April 8, 2013 at 2:54 am

I feel your pain! I love different things about WorkFlowy, Trello, RememberTheMilk, and Asana, but I can’t settle on just one. It’s so frustrating! In fact, that’s how I came across this post – I was searching Google for “Workflowy Trello” in hopes someone could definitively tell me which one is best (even though I know it’s a personal choice).

All I know is, I need to pick one and go with it, but as you have, I’ve abandoned all of them at some point. Same with paper lists and same with a simple spreadsheet. Grrr!


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