forest signals

A lazy man’s successful war on email

(reposted from my old blog to maintain a copy…)

Like essentially everyone I know, I have struggled under the weight of an overflowing inbox for almost as long as I’ve had an email account (something like 15 years now). Like my smoking habit, I’ve tried countless times to wrestle email into submission using an endless stream of productivity strategies, tools and gizmos: GTD, ‘Take Back Your Life’, Good Experience/Bit Literacy, Gootodo,Logitech IO pens, Hipster PDAs, Moleskines, and the good ole “Leaving Emails I Need To Work On as Unread” system. None of them have really stuck, mainly because there have always been key pieces that take more effort than my lazy ass is willing to put into them.

After a lot of thought (I’m intensely diligent when it comes to enabling my own laziness) I’ve come up with a system that works for me. It borrows bits and pieces from most of the things I’ve tried, but far and away the closest to what I do is Merlin Mann’s Inbox Zero. I’ve been using it successfully for about 6 months (including the massive email task of returning from two separate vacations) which is huge for me.

Note on my environment: I live in an Exchange world, so even though I use OS X at home and work, I run Outlook 2007 via Parallels. Entourage is a great product, but I’ve found there are little bits of Exchange integration that I rely on that it doesn’t do. I’m assuming you have the ability to file email to folders and a robust, integrated calendaring solution. There are certain little tricks described here that may or may not work if you’re using Mail.app/iCal, Entourage, Gmail, but you should be able to accomplish everything using any modern mail/cal system.

(Edit: I’ve now moved almost completely over to Entourage 2008. It works beautifully with our Exchange environment. The only thing I can’t do is book a meeting room… grrr)

Also, though I use an iPhone, I carry a separate Windows Mobile phone that does nothing but exchange stuff (email, calender, contacts)– an HTC TyTn running WM6 (update: now carry a Treo 750 WM6 along with the iPhone) in case you care. Again, your setup may differ,but I find having a well-integrated mobile client for mail/calender/contacts is critically important for me, as I’ll describe further down.
If you’re ready to give it a try, I’d suggest carving out 2 hours of time to set yourself up. Schedule it now on your calender. I’ll wait…

Step 1: Watch this. It will take an hour, but Merlin is a really smart and entertaining guy and it will psych you up for what is to follow. (It also provides a small and somewhat terrifying glimpse into Google’s email culture, which is also entertaining and fascinating). I don’t follow everything he suggests but the tenants are the same.

Step 2: Create a folder called “zOld mail– YYYY/MM/DD”. Select the entire contents of your inbox, and drag them into that folder. You now have an empty inbox, achieving 90% of your goal.
Do not worry about going through it, sorting it, taking action on any of it. If you were going to do that, you would have done it already. You are a lazy asshole. Admitting it is the first step in allowing yourself to be a lazy asshole with an empty inbox. If you really need it (you won’t- we’ve already covered that.. but just to humor you) it’s still there.

You probably have the remnants of an old email filing structure. Drag that in there, too. It didn’t work for you. I know it didn’t because you’re reading this stupid post. You are lazy, remember?
(Note: the zOld is kinda funny if you say it out loud “ze Frank, ze old….”, but more importantly it drops that folder to the bottom of your mail folders, getting it out of the way. The date at the end is a preemptive acceptance that you will probably lapse at least once in the future and will want to keep things straight when pull yourself together again.)
Step 3: Create a maximum of 2 folders called ‘@ Project- XXXX’.

• Name the first project folder for the main thing you do. I’m talking seriously broad here. I manage the entire video business for MSNBC.com, leading our efforts in sales, editorial, technology, marketing; the whole lot. 90% of all email I receive relates to video in some form or fashion. I have a project folder called “@ Project- Video”. That’s it– ALL of the email relating to video that I need to save goes in there.
• Name the second project folder “@ Project- Other”. This is where you will store everything work-related that didn’t fit into the first folder. If your job is so varied that no one thing stands out, no matter how broad, ONLY MAKE ONE FOLDER.
  
• You may think, “How the hell am I going to find anything if everything I do is filed in one or two folders?” I’ll get into a bit more detail later, but the bottom line is, you just will. You’ll probably remember who sent what you’re looking for, sort by name, and find it quickly. If you don’t, there’s always search. And there will always be search. You do not have to worry about some technologically apocalyptic future wherein you’re required to port all your mail to a VT100 terminal based Pine system. Gmail (and mail search) will only get better…
  
• The @ symbol (stolen from GTD) serves a different purpose here than it does there. It simply allows these folders to sort alphabetically to the top of your folder structure, making them easier to access. You’ll be using these fairly frequently.

Step 4: Create a folder called @ Follow-up. This is the most dangerous thing you will do, but you’re a grown-up and you must learn how to wield this power. This is where you will put all email that you can’t respond to today (for any reason) but need to at some point. Pay close attention later when I describe how to use it.

Step 5: Create a folder called @ To Read, then filter like a madman. This is an ongoing process, but the gist is this: any email list, alias, or notification messages that do not directly cause you to do actual work should be filtered into this folder. Think of this like your email RSS feed– it’s there for stuff that you want to/need to read, but you are not required to act or respond. 

Step 6: This is optional, but if you have a mix of work and personal mail in one account (as I still do despite best efforts) create a folder called “Personal”. This is where you will file anything you want to refer to later that’s not work related– that link to the Youtube video with the cat shooting a machine gun, the sexy email from your boyfriend that you want to lord over him later, whatever.

Laws of the Lazy Inbox:

1. Delete ruthlessly- I mean seriously, pathologically Jeffery Dahmer ruthless. No fear, no doubt. You’ve got to learn to enjoy it, like popping bubble wrap or killing a determined mosquito. Email is a time-shifted communication medium. You are (probably) not gathering evidence for a lawsuit. You don’t record all your phone calls, do you? Why are you freaky about email? Don’t be. Let it go. Unless you have the memory of a brain-damaged goldfish, you’ll be able to recall the gist of what people said, want, etc. well enough that you don’t need to save their messages like they were the Chalice of Christ.
   • Note: This is where the mobile device comes in for me most of the time. Any moment I have to spare I fire up mobile mail JUST to delete stuff I don’t need to read and/or save. Don’t respond, don’t think about acting, don’t worry– just clear things out for when you’re ready to get actual work done. This is also why an iPhone/Gmail sucks– deleting mail on the phone does NOT delete it from your inbox, defeating the whole point IMHO.
2. If you just can’t delete it, can’t or aren’t expected to do anything about, but want to save it for future reference, file it in one of your @ Project folders (or Personal if it fits). The beauty of your filing system is that you could train the above-mentioned, brain-damaged goldfish to file your damn email. No thought. Get it out of there.
3. If you actually have to do something, you have exactly 4 choices.
   • Respond right now and delete (or file if you must). If will only take a minute or two to do it, this is always the best course of action. Answer the question, pass the buck, ask another question, whatever. Don’t read too much into or overthink the email. If your boss asks you to save the earth from environmental collapse, just try to take that first step in the process: forward the message to Al Gore and get it the hell out of your inbox.
     
   • If you don’t have time to do the thing in the mail right now, grab the email and drag it into your calender. Block out a date and time to accomplish the thing inferred. In Outlook this is really simple– literally drag drag the mail from your inbox over to the calender button in the lower left. (update: In Entourage 2008, it’s even easier. Just highlight the message and hit ctrl-e) It’ll automatically create an appointment with the same subject and body as the email. Just pick an open time and hit save. Don’t overthink when to schedule yourself, or get all fancy trying to describe your task. Just pick some free time and move on. You’re lazy but you’re not a freakin’ idiot. Be generous with the time– even if you think something will only take 15 minutes schedule yourself for 30. If you don’t need the time, maybe your bladder will.
   • If your action is required, but you have to wait for someone or something else before you can act, you’ve found the ONLY use of the @ Follow up folder. As an example: Say your boss is asking for that TPS report. You’ve done your part, but you’re waiting on one of your underlings to finish his. Send your underling a reminder (or drag the mail over to your calender to remind yourself to walk over and beat your underling) then put your boss’s email in the @ Followup folder. Note: you should look at items in your @ Followup folder like inmates on death row in Texas. If they sit there for more than a few days, you better either schedule yourself to get the thing unstuck, or just freakin delete it and hope you don’t get fired. They will not solve themselves– this is the most vital thing to understand and the most dangerous part of the whole system.
   • Last option: delete it anyway. This sounds insane, but you often just know you’re never going to get around to doing whatever is being requested of you. Emails from distant friends and relatives often fall into this category. You want to reply, but how often do you really? You have to be brutally honest with yourself. Either schedule some time to do it properly, or just kill it off. It sounds cold, but do you ever screen your caller ID? Hmmmm…. think about it.
     

Further basking in the abject brilliance of the lazy email system

1. You’ll notice that there’s no task list in this system, only a calender. Lazy people should not be allowed to make their own decisions. They need to be told what to do and when to do it, in what order. You’re essentially tricking yourself into telling yourself what and when to do stuff. Neat, huh?
2. Given the importance of the calender, you must respect it. If you don’t get something done in the time allotted on your calender item, reschedule yourself until its done.
3. Calendar-dragging-fu works against your enemies even better than against yourself. If you ask someone for something and they give you the brush off (”get back to me next week”), just drag that email into your calender and set a time to get back to them when they said to. They’ll be so freaked out that you remembered that they’ll probably actually give you what you want.
4. If you’re, say, a consultant who manages 5 different clients at a time, the 1 or 2 folder filing system may sound like utter lunacy, but it’s key to the system and I strongly encourage you to give it a try. The less time you spend worrying about mechanically processing email, the more time you’ll have to be a badass consultant dude. Do more of what they’re really paying you for and let search do the heavy lifting of information retrieval. Let computers do their thing. They’re getting pretty good at it.
5. Taking notes: Just do it in email, then email them to yourself. At that point, you can process it just like anything else. If you need to clean them up and send them along to your team, just drag to the calender and schedule some time to do that. If you just need them for your own records, put them in your @ Project folder.
6. ‘Ubiquitous Capture’ is all the rage in GTD circles (with their almost fetishistic Hipster PDAs and Moleskines) and for good reason. It’s critically important that you capture things for later follow up while you’re on the go. This is another great reason for the well-integrated, brick-sized QWERTY email phone. Again, just shoot yourself a quick, subject-only email to remind yourself, then process it when you’re back at your desk. If you have a little more time, go ahead and create a calender item right there on your phone. If you’re a dumb-phone kinda person, I suggest carrying a pad of sticky notes that you file in a personally annoying place (like stuck on the front of your dumb talk-only cell phone) to make sure you don’t forget or lose them.
7. Advanced lazyness: Now that I’ve gotten more comfortable with the system, I’m ok with leaving an email in my inbox for a few hours at a time, knowing I’m going to get to later in the day. But you can’t make a habit of it, and I strongly suggest not allowing even that for the first month or two.