I’m obsessed with organizing things, and have been since I was a kid: endlessly writing down lists and plans, alphabetizing my book and music collections, compulsively reading every book in a series, etc. Perhaps because of this, I’m an organization tool junkie; I’m always eager to kick the tires on a shiny new technology or system that promises to help me deal with my little problem. Having tried many different tools, I now rely on just three. Here they are:

Pivotal Tracker. This is the single tool I use for managing software projects at the designer/developer work item level. It’s great… very easy to use, full history tracking, lives in the cloud (backed up), optimized for software projects, predicts dates for me, and lets me organize work into a few logical buckets. Some people don’t like the automatic date prediction, and if you need to work that way (“Precisely Scheduled Project Candy-Cane Land”) then it is not the tool for you. I think Pivotal would also work for many other kinds of creative project work — not just sofware — and I’ve suggested this to the good people at Pivotal Labs a few times, but they seem locked on the software space. All the better for us nerds.

Trello.  Trello is my single “big picture” list-making tool these days. At work I’ve just started using it for tracking high-level work project deliverables, e.g. key milestones and handoffs with clients. At home, I use it with Katrin to plan our expenses, prioritize home improvements, track movies, music and books we’d like to buy, and more. It’s simple, visually beautiful, and works on our computers, phones, and iPads. I’ve only been using it a few months now, but I think this one will stick because it addresses so many of the failures that stopped me from using other list-making tools.

Text files. When I’m keeping scratch notes on a project, or drafting a blog post, or trying to organize something that doesn’t fit into a list, it goes into a text file. I write in either straight .txt format or MarkDown to get a teensy bit of formatting. Every file is named yyyy-mm-dd-the-topic-title.md, e.g. “2012-01-27-writing-about-startups.md”, and this gives me a clean way to organize files and rediscover stuff I wrote months or years ago. Within software projects, a few text files in the doc directory suffice for readme’s and specs, and they get stored in our git repository for backup. For personal stuff, gitdocs automatically backs up my docs directory to the cloud. If I need a fancier looking document I generally switch to Google Docs, as I hate trying to reconcile and merge copies of office docs. But I always miss the speed and simplicity of editing a local text file, and I find myself back in text files before long, ast least for the initial drafting step.

Here are some tools I’ve tried that didn’t work well:

• Rich text “office” docs stored on a file server, e.g. Word, Excel, StarOffice, etc. plus file servers, Sharepoint, DropBox, etc. The richness of these document formats is fantastic for loosely structured content, but I find I always get caught up in formatting content and rearranging it on the page instead of getting down to the real work of writing. (Now that I write code for a living, I grit my teeth when someone sends me an amazingly formatted rich text document. “How long did that take to do?”, I wonder, and “how much better could the actual content have been if you hadn’t spend so much time formatting?” Sorry, all you devs I spammed with beautiful specs at Microsoft.) I’ve also never found a filing system that worked for teams… they all turn into junkyards, and then into graveyards. So I try only to go here when I have to work with big, bulky documents, e.g. video, PhotoShop PSDs, and such.
• Calendars, e.g. Google Calendar, iCal, Outlook/Exchange. Some people are huge fans of putting everything on a calendar, arguing that it forces time-based tradeoffs, thereby avoiding overcommitment. I find this too constraining. It forces me to think of everything in half-hour or 1 hour chunks of time, which isn’t a natural fit to the kind of work I do right now.[1] It limits my flexibility in deciding what to work on at any given moment. I don’t want silly reminder popups interrupting me every 30 minutes. My calendar drifts towards being 100% blocked out, and then I start chopping time into 15 minute segments… madness. And I find myself spending way too much time trying to optimize which day and time each thing needs to happen on. Time trap.
• Defect trackers, e.g. JIRA, FogBugz. If you have a defect-tracking list that’s separate from your feature-tracking list, it’s easy to ignore, because it’s one more thing to pay attention to. Plus you have to continually make arbitrary decisions about whether something is a defect, a feature, or in between (“by design”, “spec bug”, etc.). This is a waste of everyone’s time… who cares what you call it, the question is “are you going to do it, and if so, when?” What’s more, the same people who build features are usually responsible for fixing bugs. So I try now to avoid the disconnect by using Pivotal, which combines “bugs”, “features” and “chores” into a single work list.
• Project schedulers, e.g. Microsoft Project, or Excel for critical paths. Gantt charts and the like are pretty, and the promise of accurate schedule prediction is enticing. But they’re a lot of work to build and maintain, and they rely on people being good at estimating work, managing risk, predicting uncertain future events, and sticking to commitments. In my experience, most people (myself included) are not very good at any of those things. So project schedulers lead you down the path of building a beatiful house of cards, only to have to reconstruct it every week or two when schedule predictions are inevitably proven wrong. They are good only for point-in-time “aspirational” planning, IMO. Some projects do need this (building a new airplane, say), but I’ve found that many do not.
• Task lists and To-Do’s, e.g. in gmail, Microsoft Outlook, Things, Basecamp, etc. These tools encourage you to break goals down into fine-grained tasks, which you then prioritize and check off when they’re done. I find I tend to put way too many things on task lists, at which point I promptly get overwhelmed with analysis paralysis. Not for me.[2]

As a rule, when I find myself spending more time organizing the work rather than immersed in doing the work, I have a broken process. At that point I stop, hit the reset button, and start over. The tools I’m using these days are great assistants: they help me arrange my plan, and then they step quietly out of the way.

Thanks Ilia for the nudge to write this.

[1] Outlook/Exchange calendaring was an essential tool for me in my last few years at Microsoft, because most of my workday consisted of meetings. But even so, I used the calendar way too much. Better to leave some ad hoc unscheduled time in the day. Give serendipity a chance.

[2] I’m not sure why I find Trello so much more pleasurable than any of the task list and to-do list alternatives. After all, Trello is at its heart a list-making tool. Perhaps something subtle in its design helps me “chunk” list items at a more appropriate granularity. I’ll have to think more on that.