Simple to-do lists and calendars are no match for today’s complex productivity needs. Productivity expert Jeff Porten walks you step by step through a system that helps you manage personal and business tasks fluidly, without having to worry that something might fall through the cracks.
All Take Control books are delivered in three ebook formats—PDF, EPUB, and Mobipocket (Kindle)—and can be read on nearly any device.
Being productive is never as simple as putting items on a calendar or to do list and checking them off. Most of us struggle with too much to do, too little time, and only a vague idea of how to plan each day so we can achieve the best results with the least stress. If that sounds like you (and especially if you’ve tried a bunch of productivity systems and found them lacking), Jeff Porten’s expert guidance may be just what you need.
As a professional technology consultant and an early adopter of both hardware and software, Jeff has tried nearly every productivity management system out there, and experimented with dozens of implementation styles. He brings his decades of experience to this book, helping you create a customized strategy that’s ideal for your needs, and—crucially—avoid common mistakes. Whether you’re a productivity junkie or someone who has struggled for years with a cobbled-together, informal task-management system, this book will help you get a much better grip on your personal and business time.
In this book, you’ll:
Review the principles of successful planning—whether for immediate projects or for long-term and someday goals.
Understand your natural working style and preferences, including comfortable habits that may not be productive but that you don’t want to change, and create a more effective workflow that fits you.
Discover the best ways to think about projects, tasks, events, due dates, flags, contexts, and more.
Choose a task-management app that’s appropriate for your needs, no matter what devices and operating systems you use, and that integrates with your calendar, reminders, notes, and the apps you use to actually do things.
Develop a step-by-step process for tracking all your events and tasks and ensuring that everything happens in the right order.
Transition from an old system to your new system without worrying that anything will fall through the cracks.
Learn exactly how to keep track of all the things you need to remember throughout the day.
Improve your time-estimation skills when planning how long future tasks and projects will take.
Solve the problem of “10-minute tasks” that become all-day projects because they have a dozen things you discover you need to do first.
Get better at managing other people (and their expectations of you).
Review how well your productivity system has worked over time, using feedback loops and suggested best practices to continually improve your workflow.
Fail successfully! If something goes wrong—from a derailing large project to a life-changing crisis—learn how to recover gracefully and improve your system the next time around.
Know when and how to make changes to meet any new needs you have, and to ensure that what you do every Tuesday at 2 PM contributes to your overarching goals and most important roles in life.
Although many of the examples in the book refer to Mac productivity tools, the advice is platform-neutral. The book contains tips applicable to any combination of operating systems, and a companion webpage provides additional details on apps running on Mac, Windows, iOS, Android, and the web.
Jeff Porten has 25 years of experience as an independent consultant to small businesses and nonprofits, concentrating on information technologies, business planning, and personal and organizational workflow management.
I just gave an interview on Brett Terpstra’s Systematic podcast, when this AppleScript I’ve written came up. It creates a link for any email you’ve selected in Mac Mail and puts it on the clipboard. You can then paste it into any notes field or document elsewhere—in most apps, it’ll automatically be treated as a link and clickable. Opening it takes you to the message. This is better than most systems of copying-and-pasting text, or forwarding email to other apps, because it’ll show you the message in its original context.
There are various tools to launch AppleScripts, but the easiest (which doesn’t require any additional software) is the Script Menu. Instructions here. Once it’s turned on, open the Script menu (right side of the menu bar) and choose Open Scripts Folder > Open User Scripts Folder. Create a folder there named “Applications”, then one inside it named “Mail”. Put this AppleScript in that folder—the script will only show up in the menu when Mail is the front application.
Select a message, choose the Get Message URL script, switch to any other app, and paste the clipboard into any text field. Done. Usually you’ll see something like this:
…but some apps (like Mac Calendar) interpret the link; Calendar shows “Show in Mail…” if you paste it into the URL field, which is really weird because you need a script like this one to get the link in the first place. You’d think Apple would have set that up as a Mail command by now. If the link isn’t clickable, almost always you can select it, right-click on it, and choose Open URL from the contextual menu.
Just now realizing I can’t post attachments here, so head over to my website to pick up the script. It’s free for anyone who’s bought the book.
Unfortunately this didn’t come to my attention in time to include in the book, but OmniFocus 3 for Mac is due in September. No official word yet on when it’ll be available in the limited web version for other devices.
Try these two statements on for size, and how you would react to hearing them:
“I have diabetes, and every day I take insulin and watch my diet. If I get really sick, I might need to go to the hospital.”
“I have mental illness, and every day I take medication and watch my mood. If I get really sick, I might need to go to the hospital.”
Not quite the same, was it? Sure, you probably felt sympathy in both cases—but let’s say you heard that from two teenagers applying to be your babysitter. You’d treat them both the same? If your answer is yes, congratulations—you have better attitudes about mental illness than many of the mentally ill do.
Note: If you just thought to yourself, “Well, diabetes won’t affect my kid, but a crazy person might,” guess what? Diabetes can make you crazy. It’s true! So perhaps think twice about using that word next time?
Fact: Your Brain Lives in Your Body
It’s not a universal cultural thing, but it’s definitely American: we take physical illnesses seriously, but treat mental illnesses as if they’re personality quirks.
Just look at the words we use. “Physical” illness. “Mental” illness. “Mental” things live in your mind—by definition, a surgeon can’t get to them, so everyone thinks it’s more of a touchy-feely gray area. But turns out, your brain is made of meat, just like the rest of you, excepting the grisly and bony bits. We don’t have much of a clue how minds arise from the electrical activity in our brains, but the best current guess: it’s a naturally emergent effect, and it’s not accurate to think of our minds as non-physical.
When the average person thinks mental illnesses are less important or valid than “real” illnesses, that’s an annoying societal quirk, which makes the lives of the mentally ill more difficult in hundreds of major and minor ways. But the real damage is that the mentally ill live with those people, and unconsciously pick up the same attitudes.
Note: Humans are wonderful creatures capable of amazing things. We’re also astonishingly ignorant, and completely unaware that we are. This is true of most people’s understanding of mental illness. With few exceptions, if someone is not medically trained, diagnosed themselves, or has not personally cared for someone with mental illness, they are at worst dangerously wrong, and at best, not knowledgable at a level of detail that could be useful.
You’ve heard of that phenomenon where middle-aged men are too stubborn for their own good? When they experience chest pain they tough it out, instead of doing the sensible thing and going to a hospital? It’s ten times worse for mental illness. Here’s the horrible, horrible process most people go through:
First, you realize that awful feeling, or lack of capability, or inability to see things blindingly obvious to people around you, dovetails a bit with what you’ve heard about a particular mental illness.
You roll this idea around for a while, trying it on for size. Maybe you do some research on the internet. This takes months.
Eventually, things have gotten worse, but by now you’ve read a dozen internet articles, and heard from a dozen friends, telling you how to “manage” your self-diagnosis through diet, exercise, crystals, and—no kidding—wishing it away with a better mental attitude. Or you’ve found naturopathic and homeopathic “cures,” because drinking teas brewed from a dozen physiologically-significant herbs that may or may not match what it says on the bottle, and were made in Chinese factories with no oversight and no attention to dosage or adulterants, sounds safer than “Western for-profit medicine.”
Note: There is a scientific term for any alternative medicine that has been researched and proven to work. It’s called “medicine.” Anything that is still “alternative,” by definition, hasn’t been proven to a rigorous standard (which is usually a polite way of saying “to any standard”). Also note: some peddlers of alternative medicine refer to science as “allopathic medicine;” when you hear this, substitute “medicine that is proven to work.”
You try some of these things, especially the easy ones that don’t hurt or cause much inconvenience. When they fail, and they almost always do (dietary and behavioral changes certainly can help, but after diagnosis and in addition to proper care), you didn’t do it “right” or “hard enough.” There’s always a reason why a quack therapy is still perfect, and the problem is you.
Finally, after all of this—and sometimes, it’s several years later—something gives. You can’t tell yourself you’re not broken anymore. Maybe you’ve tasted, or gorged upon, some flavor of “hitting bottom.” If you hit bottom really spectacularly, you’re forced to seek help by a spouse ready to leave, or by a court.
You seek help.
Here’s the same process for physical illness:
Something hurts more than an Advil can handle, or your body just “feels weird” in an unfamiliar way.
You see a doctor, maybe two.
You get a diagnosis.
You get treatment.
Have I made my point about how fundamentally silly this is yet?
The two common disorders that I mention in the book—because they’re the ones I know best, for self-serving reasons—are depression and attention deficit hyperactivity disorder (ADHD). They are both poorly named, and these misnomers have radically dangerous effects for those who suffer from them.
The problem with “depression” is that we use the same word for all sorts of mental states. You’re depressed your favorite show was canceled. You’re depressed a friend can’t show up at your party. You’re depressed your dog died. You’re depressed for no obvious reason and you don’t get out of bed or shower for two months.
Note: On the topic of one word having two different meanings, with adverse effects, see also “theory:” the word for your opinions about the next season of Star Trek: Discovery; also the word for a scientific principle so well-established that we non-experts should treat it as a certainty, until a consensus of experts say otherwise for a few decades running. (When scientists have an informed opinion they’re still testing, it’s called a “hypothesis,” not a theory.)
This is called a “category error:” you think you’re talking about one thing, but you’re talking about something else entirely. Everyone’s an expert on their own “normal” depression, and fewer have experience with the clinical type; by definition, then, you’re going to hear much more often from people who think they’re experts on clinical depression, as opposed to people who have some idea what the hell you’re going through.
Meanwhile, the same thing happens for ADHD, thanks to both the word “attention” and the word “hyperactive.” Everyone has an attention span, and everyone loses focus from time to time, so they’re brimming with advice: “Go jogging, it’s wonderful!” My response to such people: “That’s great. Call me when you’re three hours late to your own wedding, you’ve repeatedly dropped out of college, or you’ve held 30 jobs in six years.”
Regarding hyperactivity, we have a different problem. At the risk of stating an unpopular opinion, ADHD in the early 21st century is likely extremely overdiagnosed in children, and extremely underdiagnosed in any adult old enough to have missed the grade school window we’ve established to look for it. (Of course that kid is full of energy and unfocused; he’s a child. Medicate him if he is suffering, not because his parents or teachers are.)
But hyperactivity is sometimes only a symptom in children; adults may grow out of the uncontrollable and inappropriate energy, while retaining the mental issues. As a result, they no longer identify with the most well-known symptoms, and this can lead to misunderstanding the problem. Or they simply think that ADHD is a kid thing and they’re immune.
Note: Some mental illnesses have a genetic component. If a family member is diagnosed with one of these, you’re more at risk for it. When it’s your parent who has it, it’s something you might get later. When it’s your child, it’s something you may have had for decades, and have gotten so good at masking you’re not even aware you’re compensating for anything.
For most mental illnesses, the afflicted are physiologically incapable of achieving a mental state that everyone else takes so completely for granted, they’re not aware it is a mental state.
The list of things that can ruin your life doesn’t stop there, of course. Agoraphobia, panic attacks, extreme shyness, some kinds of fatigue syndromes (for which the jury is out whether they’re physical or psychological—which for our purposes doesn’t matter); there are many wild and inventive ways a brain can break.
When to Seek Help
If you’re nodding your head while you’re reading this? Right now.
No, really. Around 20% of you are recognizing yourselves, or are being reminded of that time when you started the “trying it on” stage of considering whether you had a problem. 20% more of you are thinking about the family member or close friend who really needs to read this.
Seeing a psychotherapist or a psychiatrist for the first time is scary, no different than seeing an oncologist, because there’s only one thing you want to hear and it’s two words long. The thing is, here’s what happens in your first session if you don’t have anything wrong with you:
You talk for a while. A psychiatrist will likely walk you through a questionnaire. A psychotherapist may do that as well, or ask you a bunch of free-form questions.
The mental health expert you’re talking to comes to an initial hypothesis regarding your diagnosis, starting with whether you have one at all. At worst, this takes an additional session or two. (Mine took 30 minutes.)
If you don’t have a clinical problem, you get excellent advice about how to deal with the problems that brought you there, from someone with years of intensive education, and the experience of talking to 1,000 patients with problems similar to yours, perhaps much more severe or debilitating.
You go home and do those things. If you need more advice, you can go back. Most people kind of like it after they get comfortable.
“But wait,” you might say. “Sure, it’s easy if everything’s fine. But what if there’s something seriously wrong with me? That’s scary.”
Yes. Yes, it is. But please note: if that happens, there is something seriously wrong with you. Which other chronic, incurable, life-destroying illnesses do you apply this strategy to?
Please refer to the bullet point earlier, the one that said, “First, you realize you might have a mental illness.” That moment, the one that comes at the beginning of wasted years and needless pain? That’s when you seek help.
For my male readers: Meanwhile, if you have chest pains, go see a frickin’ doctor. And get your colon examined, schmuck.
As I write this, the book is getting published within hours and I’m still finalizing what’s going into the web materials. Unfortunately, this post is the one for which I have the least prepared right now, which I’ll fix as soon as I can.
In the meantime, here are the Big Three books about which I’ll have much to say later:
Seven Habits of Highly Effective People by Stephen Covey
One thing about life in the early 21st century is that technology is ubiquitous—a good thing if you’re a technophile, bad if you think that’s the reason we’re all on-call 24/7. We have computers in our pockets and the Internet is airborne. If you want to be disconnected, you really have to work at it.
The side effect is that we take it for granted, which means that even experts tend to overlook basic aspects of what their technology does for them. When you name a document, “Dec-10 meeting,” do you notice that it already had a creation date of December 10th? Are you constantly going to the fourth page of your iPhone to launch an app, but haven’t noticed you don’t use one of the apps in your Dock?
This chapter is a menu of ways you can make your technology work better for you, usually independent of what that technology actually is. Not all of them will work for you. (Naming a document “Dec-10 meeting” is a fine idea when you create it a few days early, and edit it a few days later; you might want to consider naming it 2018-12-10 meeting so it sorts better alphabetically, though.) It’s partially meant to give you specific implementations, but also hopefully will train you to take a closer look at how you’re using all of the tools in your system for improvements and tweaks.
There are two sections to this post:
Making the most of things that are built into your existing technology, which you’ve probably overlooked.
Approaches which can be universally applied to nearly every gadget or computer, from a more conceptual point of view.
Technology Tricks and Tips
This is a menu, not a checklist. I’ll be pointing out aspects of your computers and devices that you’ve likely noted in passing, but have never considered to be a productivity technique.
Most of the white-collar work we do is centered around files: on drives, on mobile devices (where files are usually pretty well hidden), in the cloud. But most of the techniques we use to manage them are dinosaurs from the dawn of the graphic user interface in the 1980s (which in turn were based on far older paper systems). Today, you can do better.
Storing Files in Apps: When to Do So, When to Avoid It
Most productivity software has the ability to attach files to tasks or projects. Usually there’s a paperclip icon or an Attach File command, which looks similar to attachments in email. But email attachments are always copies of your files. App file storage is different.
Some apps actually make a copy and put it somewhere—stored in a database, or hidden in a folder that it has access to. This makes your task app data bigger, sometimes really big if you do this often. It can also radically slow down how quickly your system backs up and syncs to the cloud. But like any copy, if you edit the file your changes won’t appear in the copy in the task copy. Double-click the one in your task app, and you’ll accidentally be in a different file than the one you see elsewhere.
Some apps create aliases or shortcuts to your files. They don’t increase size, and when you open them, you’re working with the original file. This is usually better, but now your file won’t cloud sync automatically, and if you delete it because “it’s in your task app,” it’s gone. There’s only one document, you never copied it.
Some apps let you do both, and choose on the fly. Very few people should do this, it maximizes the opportunities to get it wrong.
My recommendation: don’t use this feature except to provide a rapid-access way of double-clicking a file in your task app. Organize your files on your desktop (see below), and create a pointer to that instead.
Use Your Desktop
Computers have various special folders, mostly places where you shouldn’t muck about so everything keeps working. But there’s one special folder that’s set aside for you: your desktop. Most people either subscribe to a clean desk policy and keep nothing there, or keep everything there and make it into a horrible mess of hundreds of documents, cleaning up only when they run out of room in the grid.
Both are unproductive. Your desktop is the only place where you can visually get a heads-up of all of your work, at any time. You can temporarily group files together in virtual space. You can more permanently create arbitrary folders and give them specific names related not only to a project, but to the specific task they’re related to. And you can drag all sorts of things out of browsers and other applications to create files, a fast way of putting things in a desktop collection point (which gets a recurring pointer in your task app).
Note: Turn off “snap to grid” if you want to make messy piles of icons when organizing, but when you’re done, you should put each pile into a folder on your desktop. Computers aren’t very good about storing the locations of your icons, and they can get “cleaned up” for you when you’re not looking.
In other words, the only files that should live on your desktop are your current work. A glance tells you what to do when it’s an implicit task, and also creates a heads-up on how many open projects you’ve got going. When you’re done with a file, put it elsewhere (suggestions below). Set a recurring pointer to review your desktop and make sure that nothing lingers from completed tasks. As for the files that should be there, you can take two approaches:
If a file is an implicit task, set a pointer to the desktop to remind you to deal with everything there.
If a file needs a little more prep or explanation each time you start, or if you know you’re just not going to get to it for a while, document its task in your task app. You can still leave working files on your desktop (or organize them in a folder on your desktop), but put files for on-hold projects elsewhere. Cluttering your desktop cuts down on its value.
Note: If your desktop is starting out as an unmanageable mess, create a new folder named “Previous Desktop,” and drag all of your files there. Instant cleanup. That folder is probably a collection point now (that nothing new should be added to, but which needs to be cleaned out), so set up a recurring pointer or sprint to deal with what’s there.
This is how my desktop looks at the moment:
This is a plain old Mac desktop, but most of the files here have been tagged so they sort by the colored dots. You can keep your desktop sorted by tags (changing tags or creating new files always re-sorts them immediately) like this by choosing View > Sort By > Tags, or you can do a one-time sort (new files go wherever you put them, and tags don’t stay sorted) with View > Clean Up By > Tags. Anything on my desktop that isn’t tagged is a new file I haven’t organized yet; this way, my desktop is a combination of organization and collection point. Here’s what my tags mean (I use a lot of tags):
Note: This is an extremely geeky tip, only for people comfortable using the Terminal. Homebrew has an excellent command you can install called, well, tag. This allows you to do all sorts of things at the commmand line far easier than in Finder—and with the AppleScript do shell script command, far easier in your AppleScripts.
Maybe Use Other Special Folders
Your home folder has other default folders that you might think you should use for organization. But it’s not always the best idea.
Many of these have special attributes. Put anything into a Dropbox or Google Drive folder, and it’s in the cloud. Your Music folder may have subfolders dedicated to iTunes and other music apps; mess with these accidentally, and watch your apps break. Plenty of apps feel free to stick new folders in there wherever they feel like. That’s an argument to leave special folders alone, and create new places to organize the stuff that looks it should go there. Best place: the Documents folder inside your home folder (although it also suffers from the “apps add new folders” problem).
On the other hand, having a Music folder and a Documents > Music folder is just messy. If you can figure out what you’re doing, and remember not to touch the special folders, go ahead.
Note: If you have two such folders, and find yourself going to the wrong folder often, make an alias or shortcut from one to the other so you can quickly get there.
Assign Better Filenames
Quick: that document on your desktop that’s named, “Joe letter.doc.” Which Joe, and which project? If you know, no problem. If you don’t, use better names.
Names can be temporary. Give your file one name on the desktop to remind you what to do with it. When you archive it, rename it to what you’ll remember to use when you search for it later. A file on my desktop might be called “Joe Kissell.doc,” then get filed away as “Pitch to Joe Kissell re Take Control productivity book.doc.” Alternatively, make the file the only item in a folder, and name the folder with a instruction; I might create a folder named “Finish the book outline and add a cover letter,” put the Joe Kissell.doc file into it, and suddenly my task is implicit. When I’m done working with it, I file the document and discard the folder.
Note: You can also use File > Get Info on Mac or file properties in Windows to set a comment for a file. These aren’t as useful as they might be, because the comment can’t be seen easily. This is a good place to put search keywords, though, if they don’t appear in the document.
Make Copies Without Making Copies
It’s frequently useful to put a document in multiple places. It’s also an excellent way to accidentally destroy your documents, or your project, if you’re not careful—multiple copies mean the chance to put multiple changes in very different places, and send what you think is a finish document that’s missing half of what it should have.
There are three ways to put a file in several places, and each one is different.
You can duplicate the file. But that creates a problem when you make edits, because they won’t be in the other copies.
You can create an alias (Mac) or a shortcut (Windows). An alias looks like a copy of the original, but it’s actually a pointer to it. Alias icons have a little arrow in the corner to remind you of this; their default filenames also say so, but you might change those. The downside: delete the original “because you have copies elsewhere,” and the pointer goes nowhere—the document is gone.
Mac users have an oddball third option, called a “hard link.” Hard linked files look like aliases, but so far as the hard drive is concerned, the files actually live in both places. Delete the “original” (in quotes, because your computer doesn’t care), and the file keeps living elsewhere. A file is only deleted when all of its hard links are gone—the original has the first one.
The problem: this is a feature Macs inherited from Unix, and there’s no easy way to do it. And I’ve noticed that the Finder and Spotlight can get awfully confused by them, showing weird results. Again, only use these if you’re comfortable in the Terminal; here’s how.
Some people sync files to the cloud too infrequently, others too often.
If you’re in the habit of only syncing files to the cloud to share them with other people, consider sharing them with yourself. Cloud files can show up on your mobile devices, and are a handy way of always having them on a second screen, or on the go.
On the other hand, sharing too many files can cause ownership problems. Anything that lands on a work computer (in the US; varies in other countries) can be inspected at any time by your bosses and IT staff. Worse, they can claim sole ownership of those files, and take you to court to force you to delete all other copies. I’ve never heard of this happening with productivity app data, but it’s certainly happened when a vindictive former employer wanted to steal private intellectual property.
The other problem is that private files in the cloud are, well, in the cloud. Once they’re there, they’re out of your control. Cloud services are usually trustworthy about encryption, and making sure other people can’t get access—but if it’s not in the cloud, you’re 100% certain about it.
For this reason, I recommend against productivity tricks that put everything in the cloud. Some articles recommend buying unlimited (or very large) cloud storage, and making your cloud folders your main Documents folder. Macs allow you to sync your entire Desktop and Documents folders, and appallingly make this an easy-to-miss default during some macOS upgrades. Turn these off.
Note: Some online backup services, such as Backblaze, can be used as an ersatz cloud service for your entire drive. You can download individual files to your computers or mobile devices; the only issue is that you have to wait a bit for it to get there.
Stop naming copies of files “Big Report Final Final FINAL this time I mean it Final.doc.” Mac and Windows automatically keep a revision history in most apps. Save your changes in one place, and only make copies when you’re certain you want to freeze something in place for posterity. If you go back to one of these, hide the newer versions somewhere for reference only, and stop editing them.
Note: While it’s fine to rely on apps auto-saving your documents, and on your OS to maintain a version history, it still doesn’t hurt anything to hit Command-S or Control-S whenever you finish a bit of work you want to make sure is neatly stored somewhere, in case your dog chews through the power cable.
There is more to come here, but I haven’t had time to reformat the rest for the web. Check back shortly. —Jeff