From Office Slave to Paperless Ninja

I have already written on the joys of cleaning house and how less is more when it comes to possessions.

But possessions aren’t limited to the physical realm. Your digital files – documents, emails, music libraries, photos, etc. – share many features with property, especially as regards the need to keep them well organized and consistently backed up. Then there is the world of tasks and commitments. Left unchecked, they will proliferate, and come to weigh down you down as surely as a surfeit of trinkets. But most people devote nary a thought to this very important element of life, let alone approach it in an organized and systemic way.

Going paperless and streamlining everyday life certainly appeals to people. Banks, shops, and utilities companies offer electronic statements and receipts. Tim Ferriss preaches it in bestselling books. The tech giants offer clouds, companies peddle software and productivity apps, and entrepreneurial gurus hawk “systems.” But faced with this avalanche of information, many people don’t know how to bring it all together, and their work and life habits remain as ossified and unproductive as before.

I do not say I have the best or most comprehensive solution. I do, however, say that I have a pretty damn good solution, or else I wouldn’t have bothered writing about it. Even better, it is immediately actionable, and 100% free (barring your computer and cell phone). I promise you that if you implement even parts of it, you will not only see immediate increases in productivity but a newfound feeling of psychological wellbeing as automated routines begin to care of the myriad minutiae that are not immediately actionable (“Buy eggs”; “Do problem set 4”; “Write blog post on productivity”) that we nonetheless have no choice but to store up and let loose to wreck havoc in the recesses of our minds.

The end goal is to become a cybernetic paperless ninja. He is unburdened by surfeit possessions, but has exceptional access. He never looks at his calendar, but never misses a meeting or appointment. He doesn’t spend (waste) a single moment of his life reminding himself of minutiae, and instead uses his brainpower to learn and to focus on the big life goals. To paraphrase David Allen, his mind is like water.

The Power of Evernote

Download Evernote.

This is the central element of our system. Some of you might view is as just another note-taking program. We will transform it into nothing more or less than our second brain.

The one that keeps track of trivial but essential crap so that you don’t have to.

Evernote is a free program (though a paid upgrade is well worth it for power users). You can create notes there, as text files, or as images, videos, or other attachments. Crucially, these notes aren’t only stored in “Notebooks” (the equivalent of Folders) but can be linked together via “Tags.” This allows us to convert it into an exceedingly powerful task manager and organizational system. The information is stored in a cloud, which can be accessed and manipulated via a Desktop application (works offline), a web browser, and your cell phone.


Most of the following draws from the The Secret Weapon, an organizational system developed by the Brain Toniq drinks company. (I highly recommend you check it out yourself, especially for the explanations and philosophy behind the system, but that isn’t absolutely necessary to benefit from it).


You create notes about tasks: “Do the laundry,” “Install such and such a program,” etc. If a task is exceedingly long and/or complicated, make it a project instead (e.g. “Overview: Moving House”), with check boxes/hyperlinks designating its associated subtasks. Now organize these tasks and projects in the following manner:

Create the following Notebooks:

Cabinet – This will contain your life notes, your documents, various clippings from the web and elsewhere, and – if you wish – a diary.

Actions Pending – This will contain your tasks, both immediate and long-range.

Completed – Upon completion, tasks in Actions Pending are transferred to this notebook. You can think of it as a tasks archive.

Now set up the following Tags.

.What – A list of broad categories (e.g. Business; Learning; Self-Improvement), specific projects (e.g., for me –, or some combination thereof. In short, the activities and themes that characterize your life.

.When – Within it, create the following sub-tags: 1-Now, 2-Next, 3-Soon, 4-Later, 5-Someday, 6-Waiting, and !Daily. This allows you to organize your tasks by their priority level, so you will always know what to do next. Though you can and are encouraged to experiment around with this to see what works best, in general those tags mean the following: 1-Now refers to tasks that you want to do right now; 2-Next refers to tasks you will do immediately after the 1-Now tasks are done; 3-Later is within the next day or two or three; 4-Later is within a week or two; and 5-Someday is sometime within the next few months. The 6-Waiting tag is for things that you can’t act on at the moment, e.g. you want to get back to someone, but you can’t do it before they reply to your email.

The !Daily is for things you want to do or check daily, e.g. floss your teeth (if it isn’t a daily habit and you want to make it one). I also insert “Overview” tags onto major projects I’m working on into this tag, because it gets checked daily and I can keep close track of my progress on them.

You can also add !Weekly and !Monthly tags (I prefer to insert them as subtags within !Daily so that they don’t appear on the front page) where you can track more long-range projects, e.g. Fitness – Do 100 press-ups in one session. No point in checking it daily or even weekly, but it’s worth getting back to this goal every month or so.

.Where – Where the tasks takes place, say @home, @online, @work, @university, @London, etc. Add these as subtags. No hard and fast rules here – whatever works best for you. If you are visiting a city for a limited amount of time, and you need to do a bunch of tasks there (e.g. get document from land registry; visit such and such a friend; etc), this is well worth exploiting.

.Who – If the task involves somebody else, add them in as subtags: # John Smith, # Amanda Waters, etc. This also augments your social intelligence, as once your database gets bigger, you can click on your contacts and quickly see the interactions you’ve had with them, even if you hadn’t been in contact with them for years. When meeting you, they will feel like it hasn’t been a day since they last saw you.

.Wherewithal – This is my own contribution to The Secret Weapon. The gist of it is that much as we might wish otherwise, we only have a certain, limited stock of energy; we can’t automatically work at tasks night and day. So the idea is to give each task a rating based on the time it demands and its complexity. Insert the subtags &0, &1, &2, and &3. As a rough guide: &0 is simple and takes a few minutes; &1 takes half an hour; &2 takes an hour or two; and &3 can require a half-day to a day of focused effort (there is no need to have &4 or higher, because at that point the tasks become Projects that are best split up into subtasks).

The Cabinet

Create the following tags: .Brain, .Diary, and .Docs.

In .Brain, organize as you see best. Personally, I have the following subtags: “life”, “scribbles”, and “world.” The “life” tag has subtags on the elements of life that I’m interested in living and in developing – fitness, game, productivity, skiing, travel, etc. with notes and clippings on said subjects. The “world” tag has subtags on things that interest me but don’t directly relate to life and/or self-improvement, e.g. “history,” “languages,” “politics,” “China,” and so on. The “scribbles” tag has subtags like “books,” “movies,” “reviews,” “excerpts” (most of these are printouts of the highlights I make on my Kindle files), “notes” (notes on books, movies, etc.), “cheatsheets” (these are hand-crafted, very information dense notes on particular topics that are worth reading when you take up some activity again after a long break), “quotes,” etc.

The .Diary tag contains any notes you make about things you did today. Can be tied in to the subtags under .Brain, e.g. if I skiied today, I will tag it as “.Diary” and “skiing.”

The .Docs tag contains documents: Printouts, scans, photos, etc. I subdivide it into the following subtags: $archives (docs that are now obsolete), $cards (business cards or contact details – and are co-tagged with .Who), $core (the most important documents), $projects (docs related to specific projects, with sub-subtags for each project), and $what? (empty tag containing sub-subtags relating to the “sphere” of each document – e.g. $education, $finance, $medical, etc).

So what are you waiting for? Start scanning your documents, receipts, etc. and uploading them. You don’t need 95% of them. The only ones that really need a physical copy are stuff like passports, driving licenses, birth certificates, etc. It is possible to encrypt individual notes and this is of course highly recommended in the cases of particularly sensitive documents.

Congratulations! You are now paperless, and you no longer have Word documents with to do lists and disjointed notes on various subjects floating around on your hard drive and your email. It’s all in the Evernote cloud.


Most people’s inboxes are a right mess, inundated with unreplied-to emails, subscriptions they are no longer interested in receiving, promotions, and to do tasks send to themselves for lack of anywhere better to put them in.

It’s time to clean out this bitch.

Go to a point approximately a month ago, and start mass archiving everything. Archiving removes emails from your sight, but doesn’t delete anything, so it will all still be searchable. After your finish that lengthy task… download the Evernote Web Clipper.

The Web Clipper allows you to clip text from, or an entire page, from your web browser and send it to Evernote, while simultaneously assigning it to a Notebook and tagging it. Alternatively, you can send the email to your Evernote directly, using “@” to designate the target Notebook and “#” the target tag.

From now on, perform the following test on emails:

  • Can I reply to this now/within 2 minutes? Then do it now.
  • If not, then “clip” the email and send it to your Evernote as a Task, entitling it “Reply to [Contact] (on [subject])”; putting it into the “Actions Pending” notebook; and tagging it as appropriate with the .When, .What, .Wherewithal subtags / forwarding it to Evernote directly with the above titles and tags.

Then archive it, regardless of whether you reply to it now, or leave it for later. (There is an option in GMail to automatically archive email threads that you reply to).

The end result is a thing of beauty:


Second, download Boomerang for Gmail (if you use Gmail… there may be equivalents for other email applications). Boomerang allows you to (1) set up an email such that it is sent at a certain time and date in the future and (2) set up automated alerts if the recipients of your emails don’t get back to you within a certain time period – say, one week – in which you case you could send them a firm but polite nudge.

This isn’t strictly necessary for implementing Paperless Ninja, but it does largely eliminate the need for the “6-Waiting” time tag in the original The Secret Weapon system.

The Calendar is for Events, not Tasks

The calendar. It’s good to check it frequently, but many of us don’t – and end up missing out on events. Time to make this but a bad memory.

Create two calendars in Google Calendar. (This assumes you are using Google Calendar, which I recommend given its integration with Gmail).

MyCalendar – Contains “do or die” events. Well, maybe not “die,” but going to them isn’t just an option without consequences… if you don’t go to a meeting, you might get fired; if you don’t go to lecture, you might get a failing grade. You’d better go.

MyOptions – Contains events that you can go to or not depending on whether you feel like it e.g. a distant friend’s B-Day party, your Chinese language Meetup groups horse-riding excursion, a local wine tasting, that kind of thing.

Then set up the following system of notifications.

For MyCalendar, go to “Reminders and Notifications,” and click on “Daily Agenda” under the email column. This will send you an email at 5am in your time with a list of the things you are scheduled to do today. If said schedule is busy, I recommend clipping said email and tagging it 1-Now for easy consultation as the day goes on.

Second, for specific events that you haven’t yet decided whether you’ll go to or not… or which need some kind of action (e.g. an RSVP in advance, or signing up to a class), set up email reminders.


Time the email so that it arrives at about the time that the event becomes actionable on. For instance, if you wish to sign up to a class, and the window for that is 4-2 weeks before it begins, then set up an email reminder for 4 weeks beforehand.

When you get the email, use the Web Clipper on it and add on the appropriate time tags and other tags.

Clean Desktop

Here is my desktop.


Much nicer to look at than some disorganized space overflowing with random folders, disjointed Word documents, program shortcuts, and to do lists – wouldn’t you agree?

There is a good place where to keep the things you’re working on at the present moment and it’s not on your desktop, which just distracts and depresses you. It’s the My Documents or Documents folder. Here is mine:


Very minimalistic. The first four entries are concrete, currently active projects (respectively, they are my two blogs; the book I’m writing; and the media translation website that I’m developing). The Workspace is for everything else that isn’t big enough or high priority enough to warrant its own folder. The rest are just a few files that aren’t really convenient (for a few reasons) to keep on Evernote.

All the old stuff/completed projects should be archived away so as not to constitute a distraction. I prefer to file it away in my Evernote Cabinet notebook. Likewise with plans for future projects. I also store them all in my Evernote Cabinet. I can easily access them if I wish to either (1) review, (2) take up again, or (3) start working on them, but they don’t occupy “active space.”

The setup is also highly efficient and allows very quick and efficient backup. My current Documents folder is a mere 326MB. (Once upon a time, it was ~20GB).

Enter the Cloud

Everybody is talking about cloud storage, but few are utilizing it to its maximum productivity and storage potential.

Keeping your data in a cloud has several advantages:

  • Security: Somebody can steal your password and delete all your documents from the Google Drive. Or an EMP could wipe it all out. But you can also lose your laptop, or get it stolen – and if you haven’t backed up your data recently, you’re in some trouble – and only going back to pen and paper will save your data from nuclear winter (though then you might then have to burn your notebooks as fuel so the point is moot anyway).
  • Backups: Automatic and constant if there is an Internet connection.
  • Access: Not limited to your PC… you can have access to your data from any device with an Internet connection. No need to bother with tedious transfers when getting a new PC… just install your cloud programs, and let them do it for you.


  • Storage limits: Different services give you different amounts of storage space for free – we’re not really interested in paying for it, though you can – but it will surely be smaller than what you’ll get on your hard drive. This, incidentally, is another good reason for limiting the size of your Documents folder.
  • Secret state surveillance: That said, it is exceedingly unlikely they will be specifically interested if you’re a nobody like 99.9999% of people. If you are very concerned about this, there are several sites with strong encryption that claim not to have backdoors… though if you have a genuine reason to avoid state surveillance, e.g. if you are a Wikileaks member or a Deep Web baron, you’re better off eschewing it altogether.

Here is a rough schema to get you orientated:

Private Friends Public
Articles Evernote Email Blog; social networks
Documents Evernote Cloud (GD; DB) different
Music Cloud; Streaming Torrents
Photos Cloud Flickr Flickr
Videos Streaming YouTube YouTube; torrents

Articles is an all-encompassing term for things you write that are useful in some way. If they are for your own reference, keep them on Evernote; if you want to share them with family and friends, then… well, email, duh; if it’s for public consumption, then use a blog (WordPress, of course) or Facebook, Twitter, etc. (Yes, you heard that right. Anybody who is still using Facebook for things they would rather not let the rest of the world know about are… a bit naive).

Documents are things specific to your life and various projects. For personal files, there’s again Evernote. For sharing with friends, the best cloud is probably Dropbox. For public sharing, there are upload/download sites; your own hosting (if you have it); or public folders in Google Drive, Dropbox, etc.

On music and videos… to be honest, I’m not a fan of lugging about huge amounts of tunes and movies in this day and age. Cloud companies probably won’t care about if you store this material – even pirated material – on their servers, as long as you don’t share it, because (1) it’s hard to tell whether something is pirated anyway, or legitimately ripped; and (2) shafting your customers on behalf of Hollywood/RIAA/MPAA isn’t good publicity if nothing else. If one the other hand you wish to actively share your music and movies, well, I won’t tell you no of course – but I’m not expert here, so don’t ask me for advice. Use that torrents thing, I guess?

Personally, I think the future of both music and movies is streaming. It is so much easier to pay a paltry $5 or $10 per month to get access to far, far more music and movies – across multiple devices – than you could ever get in a private collection. For music, you have Google Play, which not only allows you to stream but also gives you 20GB (!) of space for your own music collection (though I have found that they have 90% of what I have anyway). For videos, you have Netflix, of course, and you also have Amazon Instant Video (which comes free with Amazon Prime, which is well worth getting if you live in the US and buy most of your things online).

Photos you had best keep on an ordinary cloud for personal use. I have made Yandex Disk – which offers a generous 10GB of free space – as my photo cloud storage choice. What is its really big advantage? You can connect you cell phone to it, so any pictures you take are automatically, immediately uploaded to there. This guarantees easy, guaranteed retrieval of any images you snap on your cell phone (e.g. that cop beating up a protester now walking up to you to confiscate your phone). For sharing with friends and the public, the best choice at the moment is probably Flickr. It offers a phenomenal 1TB (sic) of free storage, but not in a way that allows easy retrieval. So it’s not that good a choice for storage, but there’s probably nothing better for presenting your photos and albums to your friends and showcasing it to the public.

Once you’ve made your options and downloaded the cloud services you wish to use, you will want to setup a system that enables quick, automated (or semi-automated) backups.

One alternative is to just insert your Documents, My Music, My Pictures, etc. folders directly into the relevant folder on your cloud. But I see no good reason to do this… it’s not like you’re starved of HD space nowadays.


Another option, which I use, is to keep all that on your hard drive, but install SyncToy, a simple program that automatically copies things between two different folders. (You can have it be “synchronized” – things are copied both left and right, which can be dangerous if for some reason one side deletes everything; “echo” – things are copied left to right, aka in this context from your normal documents folders to the equivalent folders on the cloud; and “contributions” – things are copied left to right, with no deletions). Above you can see my current setup.

Never Forget a Password

When it comes to passwords, they always recommend you to think up of a unique, hard one for each application and keep them all in a secure place.

But honestly, do you know anyone who does that consistently?

Last Pass comes to the rescue (h/t Matt Forney). This extremely nifty application:

  • Securely stores all the passwords you care to store through one master password (which really should be unique and very hard).
  • Intelligently autofills (and auto-logins, if you wish) your username and password as soon as you get to the appropriate webpage.
  • Integrates with all the major web browsers.
  • Passwords can be organized within folders, and each entry can have additional notes (e.g. some logins are more complicated than just a username/password combo).
  • Auto-fills forms.
  • For a paltry $1 a month, the mobile version is unlocked.

Lighter than Air

One of the major problems of modern life is the sheer amount of things we have to keep on top of.

Tasks big and small, urgent and longterm; documents, notes, information, and passwords that have to be kept up to date, well organized, accessible, and secure; events we have to go to or would like to go. Everything under the sun, and everywhere under the sun – notebooks, diaries, the desktop, emails to oneself…

And all this weighs down on our souls.

Now weight is not necessarily a bad thing, mind you.

The heaviest of burdens crushes us, we sink beneath it, it pins us to the ground. But in love poetry of every age, the woman longs to be weighed down by the man’s body.The heaviest of burdens is therefore simultaneously an image of life’s most intense fulfillment. The heavier the burden, the closer our lives come to the earth, the more real and truthful they become. Conversely, the absolute absence of burden causes man to be lighter than air, to soar into heights, take leave of the earth and his earthly being, and become only half real, his movements as free as they are insignificant. What then shall we choose? Weight or lightness? – Milan Kundera, in “The Unbearable Lightness of Being.”

In other words, weight can give meaning. But what kind of meaning can said notes and tasks impart? They will just make you into an office slave.

Become a paperless ninja so you could spend your time getting weighed down by men (if you’re a chick… or a gay man, I suppose), and even loftier things like life goals and self-discovery, instead of having to be preoccupied with trivial bs.

Anatoly Karlin is a transhumanist interested in psychometrics, life extension, UBI, crypto/network states, X risks, and ushering in the Biosingularity.


Inventor of Idiot’s Limbo, the Katechon Hypothesis, and Elite Human Capital.


Apart from writing booksreviewstravel writing, and sundry blogging, I Tweet at @powerfultakes and run a Substack newsletter.


  1. Philip Owen says

    Shortest immediate operation. A welll known production engineering principle.

  2. That desktop is something to aspire to. I think it will take me a little time..