Ridiculously Easy Paperless Organization: The Big-Bucket System

For years I relied on legal pads to keep track of things. I made to-do lists, took meeting notes, doodled in the margins—all on legal pads. When I filled one up I’d stuff it in a drawer and start a new one. When I needed to retrieve old notes, I’d sort through the backlog of legal pads for what I needed. When the drawer of used legal pads was overstuffed, I’d throw out the oldest ones to make room for more.

This was inefficient, but I am okay with a little chaos, as you’ll see below. However, I’ve weaned myself off of legal pads—gone paperless, even—and I’m glad I did.

Last year I interviewed for a job at a startup. It was a nontraditional interview in which I sat in on a half day of meetings so that we could all get a sense of how I might fit into their culture. I walked in with nothing but my pen and legal pad; everyone else had laptops and tablets. “Ooh, you’re old school,” one of my potential-future-workmates commented. (It didn’t help that I was also the oldest person in the room.)

I did not get the job.

I held onto my legal pads for a few more months, until I started my new job at a large tech company last spring. At the new job, there was a months-long waiting list for cubicles. There were several open workspaces in which I could dock my laptop until I got a cube, but no permanent desk. Thus I became a digital nomad, lugging my laptop, power cable, mouse, headset—and legal pad—between work and home every day. My laptop bag started getting heavy with legal pads, and I decided then to go paperless.

Desktop/Laptop Organization

The only software I use for paperless organization is Microsoft OneNote. Before you start laughing, or Googling this program you have never head of, let me say that the software doesn’t matter. I started experimenting with OneNote and liked its flexible interface for managing lots of buckets of information. I organized notes according to work life and personal life, and then I created subcategories within each of those big buckets. In the end, none of my organization mattered because I use only one category 90% of the time. A simpler program would have done the trick. One nice thing about OneNote, though, is that it auto-saves everything and does not add clutter to your file folders. There are no separate OneNote files. Everything is available when you open the program.

So what is the one category I use 90% of the time? Meeting notes.

Most office jobs, for better or worse, are propelled by your meeting schedule. Despite all the categories I created for my notes, I found that most notes were getting dumped into a catch-all I’d created to document my meetings. Who participated? What was it about? What was decided? It became redundant to create separate to-do lists because most of my to-dos stemmed from what I committed to during meetings.

Whether or not meetings are central to your work life, the point is to create the largest and fewest possible buckets of information. Any organizational system that involves meticulous curation is destined to fail. (For me, at least).

One folder to rule them all

To organize my documents I use just one folder. It’s the default “Documents” folder in Windows 7. In other words, I don’t organize documents at all. I have tried organizing them into subfolders, but every subfolder requires an additional click and additional brainpower to try to remember where I put something. Having one folder sounds messy, but since every OS allows you to sort by most recent, alphabetically, or by file type, it’s easy to find what you’re looking for. My folder defaults to show files by recency, so 90% of the files I need are always at the top. I never spend more than 30 seconds looking for anything. It sounds crazy but it works. It will continue to work even after years of accrued files because, again, most of what I need is something I’ve accessed recently. If I still have this folder in 10 years, and it has thousands of files, I might create an archive folder. Might.


I cannot stand Inbox Zero. Email is another place to apply the “big bucket” system. I have a couple of folders for the few emails I want to save:

  1. Save—This is where I save stuff I want to save. It doesn’t really matter what goes in here, just that it’s important enough to want to reference later.
  2. Review—This is where I drop messages I want to reference again at the time of my next performance review. Congratulations on completed projects, compliments from bosses and coworkers, anything that might bolster my case when it comes time to ask for a raise.

As for everything else? I let my inbox pile up, periodically deleting everything older than a couple months. Using this method I have never lost anything important and never wasted time organizing anything.


When I was freelance, I spent a lot more time trying to organize things on my mobile device. Like a lot of people, I tried Evernote and found it too unwieldy. Other people swear by Evernote. One app I did like was Springpad. It’s lighter-weight than Evernote and also has a Chrome plugin so you can sync your mobile device to your web browser—meaning you can add a note to the app directly from your desktop web browser. I mainly used Springpad to keep track of books and movies I wanted to check out, gift ideas, and other personal lists. I didn’t use it for work but I’m sure it could be handy there too. Just don’t let it trap you into too many folders.

Trust Your Brain

The over-arching theme of the big-bucket system is to trust your brain. Not to insult the hyper-organized among you, but I think people who are super-anal about organization are often afraid of their own brains. It’s scary to let go and use the force. But one day science will (probably) conduct a study that demonstrates that there’s a 42% chance that over-reliance on to-do lists leads to early-onset Alzheimer’s. Just sayin’.

Technology-Agnostic Is the New Black

I’m going to say something really controversial here:

I don’t have a strong opinion about Apple. Or Microsoft, or Google, or any other big technology company.

Riverhead Gold tobacco, 1940s?

Brand loyalty can kill you.

It’s not that I have no opinion. It’s just that I think the big players have strengths and weaknesses and no one is consistently great at all things.

I grew up on Windows PCs, switched to Apple when the iMac and (later) iBook came out, and then switched back to Windows because it was easier to use the same OS as my employer. In the mid-90s I destroyed a PC by attempting to install Redhat Linux, but I’m sure that was just me.

A few of my opinions, as of today, and totally subject to change:

Apple’s iOS kicks ass. I had a terrible time with an early Android device, and switching to an iPhone felt like a tremendous leap forward.

Windows 7 kicks ass. I held onto Windows XP for years past the stale date, but my work computer has Windows 7 installed and I’ve grown to love it. Every time I have to do something on my wife’s Mac I’m like “WTF is this?” but I’m sure if I used it every day I’d get reacquainted . (My biggest beef with Mac’s OS 10.x is the way it tries to control the way you organize files (by date, by type, etc.). Windows 7 feels like a sensible evolution of file structure, built upon years of trial and error.)

Google Chrome kicks ass. It’s fast and and it gets out of your way. I love being able to open up Chrome from any machine (including my iPhone) and have all my history and bookmarks transfer. I used Firefox for a long time before getting sick of all the security updates, which Chrome handles seamlessly. I use IE8 at work. It’s slower than Chrome and Firefox but an improvement over earlier versions. I understand IE9 is pretty good.

Yahoo! Mail kicks ass. (Really.) I also have a Gmail account, so I know what people like about it, but Yahoo’s incremental improvements over the years have led to a damn good email client that has never failed me. I have over 15 years of email history in my Yahoo account, and maybe it’s partially laziness, but I haven’t seen much benefit in switching to Gmail (except for the obvious one of having an email address that doesn’t make me look like a 70-year-old collector of Hummel figures.)

These are opinions about technologies, not companies; I like what these technologies do for me, but I am not really a fan — let alone a fanboy — of any of the companies that manufacture them. And I think that’s how most people operate.

Rabid devotees of Apple/Microsoft/Android/Ubuntu/Etc. represent a tiny fraction of the world’s population. They just happen to be really noisy and passionate about their chosen “team,” so it can seem like you have to choose. But most users — if they give it much thought at all — choose technology a la carte, selecting what works best for them, within their budgets.

If you work in any kind of tech field, you should pay attention to a-la-carte users like me. Don’t judge us; learn from us. Otherwise, carry on foaming at the mouth. It’s pretty entertaining from where I sit.