Single File

In Bird by Bird, Anne Lamott’s wonderful book on writing, she explains the title with a simple anecdote:

Thirty years ago my older brother, who was ten years old at the time, was trying to get a report on birds written that he’d had three months to write, which was due the next day. We were out at our family cabin in Bolinas, and he was at the kitchen table, close to tears, surrounded by binder paper and pencils and unopened books on birds, immobilized by the hugeness of the task ahead. Then my father sat down beside him, put his arm around my brother’s shoulder, and said, ‘Bird by bird, buddy. Just take it bird by bird.’

And, indeed, that works for nearly any kind of project. The whole might be overwhelming, but you can invariably break it down into a series of successive projects (and sub-projects and sub-sub-projects) each small enough that you can confidently take them on.

I’ve long taken that approach to goals, working backwards from five-year (or 25-year) endpoints, to one-year, one-quarter, and one-month waypoints. With that groundwork, I can then focus on just what’s in front of me today, yet know I’m still making progress on the big picture.

Yet I’ve also learned that there’s such a thing as too much sub-division.

Previously, I’d continued all the way back to one-week and one-day breakdowns, starting each day with a list of small tasks across a number of different projects. But because I’d chopped those tasks so fine, I ended up spending my day essentially serially multi-tasking. I never got to spend long Deep Work / Maker Time blocks on a single project.

Now, I stop my breakdown at the month level, then sort the resultant project list by urgency / importance. And each day, I focus only on one single project, the one at the top of the list, for at least the first few hours of the day, before dealing with daily habits (like blogging and emptying my inbox) or small one-off tasks.

Sometimes, it will be the same project for days on end. And though I initially had some anxiety about that – felt like I was leaving the rest of my projects unduly on the back burner – I can now empirically say, having just analyzed a year’s worth of my completion rates with both approaches, that I get waaaaaaaay more done when I take this single-file approach.

In other words, take it bird by bird. But take it by the whole bird, not by the beak and leg.


I’ll admit to being more than a bit OCD in my desire for a clean and organized workspace. But, from my experience with a slew of coworkers over the years, that’s not an entirely unusual trait. Whether wild creative types or precision-minded engineers, at least 50% seemed to feel and think better when their physical environments were tidy and undistracting, with everything in its right place.

So I’m always shocked by those same people’s email inboxes, which inevitably contain thousands (or even tens of thousands) of read and unread emails. I get agita just from the thought. And, indeed, if you’re a clean-desk type, I’d suspect you, too, would feel similar peace of mind from an equally minimalist inbox.

Try it out yourself, with this simple approach.

First, move all the old stuff into a backlog:

  1. Create a folder (or, in Gmail, label) called “Backlog.”
  2. Select every email in your inbox. (In Gmail, select all using the checkbox icon at the top left, then click the “select all conversations that match this search” link that appears to get select those past the first 50 results.)
  3. Apply the “Backlog” label to all of the messages.
  4. Click the archive icon.
  5. Boom. Inbox zero.

Tomorrow, at some point during the day, your goal is to make sure you empty out every single email that has come in after now. If something doesn’t need action, archive it. If it needs a response, fire one away, then archive it. If it requires a non-email task, a longer response than you want to deal with right now, or is waiting on something, make note of it on your to-do list, then archive it. The important thing is that you get back to zero, daily.

Each day, too, pull up the backlog folder / label, and process part of the way through, starting at the top, the same way you would with the inbox. In my experience, that’s usually faster going, as an increasing percentage of the stuff no longer needs a response as you work backwards. If you have years of stuff in the backlog, once you make it a few weeks (or a month) back, you can probably just archive the balance, as there’s unlikely to be anything active, and if there is – and it’s still important – they’ll email you again.

And that’s it. That’s the recipe for inbox zero. It even works repeatedly if you fall off the wagon, and need to declare a new backlog / need to start again fresh in the future. All you have to do is make your way back to empty again each day, with only a day’s worth of incoming stuff.

People seem to think this requires extra work, but it definitionally doesn’t; if you’re going to respond to an email eventually, it takes the same amount of time regardless of when you do it. So you might as well do it within 24 hours. It’s great to feel on top of your emails. And, as I said, if you’re a neat-freak, the degree to which an empty inbox soothes / allows you to focus on real work is an order of magnitude better than a clean desk.

Dealing with Disaster

I'm a long-standing fan of British time-management guru Mark Forster, and particularly his book Do It Tomorrow.

At the crux of that book is a simple observation: you develop backlogs of work because the amount that comes in each day exceeds what you can get done in that day. Thus, preventing backlogs requires figuring out how to get a day’s worth of work done daily. That usually requires pruning commitments, reducing the flow of incoming work. ‘Time management’ alone won’t fix the problem; if there’s just more work than time allows, you won’t get it all done, regardless of how you prioritize your list.

Forster also recommends starting out by declaring a backlog: taking all tasks, emails, paper piles, etc., and moving them into a separate place – a dedicated to-do list, email folder, stack of papers, etc. You can then start each day by chipping away at the backlog. But, following that, you spend the rest of the day making sure you don’t once again fall behind. (FWIW, more specifically, Forster recommends batching all of today’s incoming work, emails, etc., and completing it tomorrow, so that you can see in its entirety what a full day of inbound commitments entails. Hence the name of the book.)

Recently, I’ve been trying to clean up a bunch of messes I’ve made in life – on the personal and business fronts. And the sheer weight of it all, the number of things I need to make right, has been a bit overwhelming.

Today, however, I realized that those messes are simply a different sort of backlog. So, this morning, I tried to list out everything I want to fix – people to whom I need to apologize or make amends, work that I need to do to feel good about where everything stands. Going forward, then, I’m focused primarily on the day before me: can I live and work today without screwing up anything new?

Sure, my life mess backlog is large. But it’s also finite. It’s a list I can chip away, piece by piece, over time. One that won’t grow any larger so long as I can keep up with living the way I want, day in and day out. And, oddly enough, just by thinking about things in that new way, it suddenly feels like I might be up to the task.

Do the Thing

“Do the thing and you will have the power.”
– Emerson

My year’s been off to a stressful start, which I’ve largely dealt with by wallowing. With too much piled on, I was having a whole lot of trouble buckling down and getting moving on my most important projects, instead frittering away days working on less important tasks, scrolling through Twitter, and feeling sorry for myself.

This morning, however, having apparently reached peak wallow, I finally sat down and banged out a bunch of high-priority stuff on which I’d been procrastinating for weeks. And, as is seemingly always the case, none of it turned out to be so bad once I actually got started. Further, though I’m still neck-deep in disaster, as all of that work hasn’t really even begun to make a meaningful impact, I feel so much better.

I realize this is hardly profound insight; indeed, it’s simple common sense that I still somehow need to rediscover again and again. But I’m posting this as both an affirmation, and as a helpful reminder to myself:

Do the thing, and you will have the power. And you’ll feel pretty great, too.

Tech Tools: Words

Yesterday, Evernote released a much-anticipated (and much-needed) update to its clunky iOS app. For many users, however, the simplicity (or, perhaps, feature-paucity) of that update, paired with the company's recent substantial price hikes to its premium service, just served to further disappoint. While Evernote was early in pioneering the idea of a searchable digital 'everything box' for ideas and notes, the slow pace of improvement, and lack of simple, user-requested features, has left a bunch of folks looking for alternatives.

I abandoned Evernote a while back, and now depend primarily on a trio of Mac apps (paired with iOS counterparts) to handle my world of text. Along with a browser (and Gmail in it), they cover about 90% of my daily computer use, so I've auditioned a slew of other options, too, and can strongly endorse all three of these:

1. BBEdit.

I started using BBEdit literally 20 years ago. Back when I regularly wrote code, this was where I did so. Now, I use BBEdit primarily to wrangle my productivity, running my life from a folder of about a dozen text files. Goals, projects, today’s to-do list, books and movies I’ve watched/read and want to watch/read, my grocery list, a workout journal, a trumpet practice log, etc. If I took one thing away from David Allen’s Getting Things Done, it was the idea of getting things out of my head and into a trusted system. For me BBEdit is where that happens.

Additionally, BBEdit is exceedingly powerful at manipulating text; you can use GREP in the ‘search and replace’ box, and for those like me whose command line skills are slow and rusty, menu items to find duplicate lines, sort lines, prefix/suffix lines, process lines containing a specified string, etc., come in handy pretty frequently, as I often end up grabbing large lists or pages of text from other sources (the web, digital books, etc.) and need to organize them into some kind of useful form.

This one’s nerd-tastic, I know, but I spend more time in BBedit than anywhere else. You can demo it free, but if it doesn’t seem worth the cost in your life, you can also default to the free, pared-down version, Textwrangler.

On iOS, I use Editorial, which is by far the most powerful mobile text editor I’ve found. And as I use Dropbox to back up my files, I can seamlessly keep the desktop and iPhone versions of my text files in sync between the two apps.

2. Ulysses.

I use this, on both my Mac and iPhone, for pretty much all the longer-form writing that I do. (In fact, I’m typing this post in Ulysses right now.) It’s a minimalist text environment that helps me focus on getting words down on the page, it effectively manages documents inside the app (and automatically syncs things between desktop and mobile), and it can quickly and beautifully export your words into anything from HTML to formatted PDFs, eBooks, or Word Docs. If you’re (god-forbid) still writing things in Word, try this instead, and make your life waaaay better.

3. NValt.

Basically, this is for everything that doesn’t go into BBEdit or Ulysses. While I use the former for structured lists and plans, and the latter for any document that might require thought and drafting, NValt is my quick and simple repository for the kinds of odds and ends that pop up throughout my day.

You can pull up NValt with a simple keyboard shortcut, and your cursor is waiting in a search / create bar. As you type, NValt shows you a list of all the notes in your repository that match your search; to create a new note, you just hit ‘return’ at the end of the line, and a new note’s created with that search term as its title. (Try it out; it makes much more intuitive sense than I’m doing justice.)

Pulling the app up right now, the most recent files include a list of links to some fancy quesadilla recipes (last night’s delicious dinner), show dates for a couple of jazz groups I’m hoping to catch in the next month or two, instructions for a pranayama breathing technique, the IP addresses I jotted down while helping to set up my grandmother’s router, and notes I’ve taken while reading Tools of Titans. It all just gets dumped in here, and I can pull it up as needed with a couple of keystrokes.

NValt also syncs with the free Simplenote, so I can search and add new notes from my phone, too.

So, that’s it. BBEdit (with Editorial). Ulysses. And NValt (with Simplenote). If you spend a bunch of your day working with text, too, I strongly recommend giving all three a try.

Totally Random

With the start of the New Year, I’ve been trying to audit my approach to productivity, thinking about ways in which I can be more effective in the year to come.

I tend to tag my tasks with relative priorities, and I keep a log of completed work from each day. So, last week, I sorted through the log entries for 2016, to see if I could find any patterns to my efficiency.

In that analysis, something quickly emerged: my daily efficiency had a clear barbell distribution, with stretches in which I banged out huge volumes of work (including my most important tasks), and then stretches in which I barely got anything done (and what little I did accomplish tended to be menial, low-priority stuff).

Thinking back to the floundering, low-productivity days, I could highlight at least one obvious, unproductive behavior: I’d look at my list, feel overwhelmed, and then simply procrastinate by avoiding my list entirely for much of the day. Whereas on days in which I was able to get cranking, I’d simply hop in and get to work, moving directly from one task to the next.

The problem, then, appeared to be one of momentum. Once I was getting things done, it was easy to keep getting things done. But if I felt stuck, I had a hell of a time getting unstuck.

This morning, I was clearly in that ‘stuck’ mode. So, picking up an older idea from British productivity author and tinkerer Mark Forster, I set out to try what he calls the ‘random method.’

In short, I went over to the Random Integer Generator, and created a table of 100 random numbers from 1 through 16. (The 16 there being somewhat arbitrary – it’s my lucky number.)

The first number on the table was an ‘8,’ so I started at the top of my list, and counted down to the eighth task. Whatever it happened to be (in this case, processing a pile of paperwork), I hopped in, did it, and crossed it off the list. Then I went back to the table – this time a ‘6’ – and counted six more tasks down, and did that task next.

If my count took me to the end of the list, I’d simply loop back and keep counting from the top. And if I landed on a task that had already been crossed out, I’d ‘slide’ down until I reached the next uncrossed task.

In that way, I randomly looped my way through a first dozen tasks by noon, accomplishing more this morning than I thought I’d likely get done all day.

I’m not entirely sure why this works, though I suspect it has to do with removing the element of choice – if I had to decide what I wanted to do next, I could simply avoid making a decision and do nothing. But if the integers ‘told’ me that I had to do something, that was just enough external pressure to spur me into action.

Admittedly, this is a slightly ridiculous approach. I’m not sure if it will similarly be able to jump-start me on future ‘stuck’ days, and it’s certainly more cumbersome than simply trying to choose the next most important or appropriate task on days when I don’t need the extra push.

But it’s something I’ll certainly be testing out over the weeks ahead. On the chance that you, too, sometimes avoid your to-do list entirely in favor of scrolling through Twitter or diving into the rabbit-hole of Wikipedia, perhaps it’s worth similarly giving it a try.

Bullets, Pages

Though you don’t hear about it much from new-fangled growth hackers, the old-school ad-men I know often discuss the concept of ‘effective frequency’: the number of times a person needs to be exposed to a marketing message before they respond.

The idea is a long-standing one, dating back at least to 1885, in Thomas Smith’s Successful Advertising. As he puts it:

The first time people look at any given ad, they don’t even see it.
The second time, they don’t notice it.
The third time, they are aware that it is there.
The fourth time, they have a fleeting sense that they’ve seen it somewhere before.
The fifth time, they actually read the ad.

Etc., etc. Smith goes up to the twentieth time, which is when he suggests that someone actually buys. Though, for a century and a half, business-focused academics have researched and debated the number of exposures needed, generally settling somewhere between three and seven.

I say this because, over the past decade, I’ve come across both Julia Cameron’s Morning Pages and Ryder Carroll’s Bullet Journal more than a handful of times each. But it was only this past week, rediscovering them both, that I decided to make the leap.

Last Monday, I broke out a Moleskine (A5, dotted) and a fountain pen, resolutely ignored my long-governing Todoist task list, and hopped head-first into analog life.

A week in, I’m still not entirely sure how I feel about it. The Morning Pages take a full half-hour of scribbling; more than long enough to cramp up my writing arm and shoulder, and to make me wonder if I’m pissing that time away with nothing but three ramblingly scrawled pages of daily nonsense to show for it. Similarly, I’m not sure whether I’m getting more or less done with the Bullet Journal than I was before.

But I do think that, with the Bullet Journal approach, I feel a bit less weighed-down, less put-upon by my to-do backlog than I do when using Todoist. And I’ve found that, if I hop into a meditation session immediately following the Morning Pages, the cloudy surface of my brain settles a bit faster, let’s me more easily reach a point where I feel like I’m looking down through the clear, calm waters of my mind, into the depth below.

So, for the next week, at least, I’m sticking with it. If nothing else else, it leaves me covered with all kinds of interesting fountain-pen ink smudges. And I have a vague sense, perhaps without enough marketing exposures to yet bring it to top of mind, that indigo blue is the new black.

Pausing Gmail

Don’t check email in the morning. Only check email twice a day. Turn off all of email notifications.

That’s increasingly standard productivity advice these days, and for good reason. We’re at our most productive when we proactively choose the things on which to focus. But email is entirely reactive – it hands control of our to-do list to anyone who happens to send a request our way.

For a while, I tried to follow that advice, cutting back on my email checking frequency. But I quickly ran into a problem: many of my proactive tasks involve sending email. Or searching through my email history. And as soon as I opened a Gmail tab, I’d find myself inexorably drawn into processing and responding to the latest messages, even if that wasn’t what I had set out to do.

So, a month or two back, I hit upon a simple solution. I set up a folder called “Incoming”, and a filter to send all of my new mail to that folder. And then I hid the folder from the label sidebar, so I wouldn’t get distracted by the unread message count.

Voila. Problem solved. Now, I can load up Gmail, send or search as needed, and still only see new stuff coming in when that’s actually what I want to do.

For bonus points, I also set up a single “Robots” folder, to hold all incoming promotions, mailing list messages, social media updates, etc.

Now, a couple of times a day, I can process the “Incoming” folder to to respond to real, from-a-person emails. And, once each day, I empty out the “Robots” folder, to see if there’s any wheat in that sea of chaff.

It’s completely changed my experience of email, and I can’t recommend it highly enough. Here’s how to set the same thing up yourself:

First, copy this string into your Gmail search box:

category:(forums | updates | promotions | social)

Then click the downward arrow at the right side of the search field, and choose “Create filter with this search” on the bottom right of the pop-up. On the next screen, select both “Skip the Inbox (Archive it)” and “Apply the Label” for whatever folder you’d like to route incoming junk into.

Then do the same thing with this string:

! !category:forums !category:social !category:updates !category:promotions

For this one, you’ll need to replace my email ( with your own, and choose a label for incoming ‘real’ messages.

Finally, hover over the names of each of those two labels, click the downward arrow that appears, and select “In Label List: Hide”, so that you don’t have the sirens’ call of unread messages perpetually in your sidebar.

Try it yourself. Seriously, this one changed my life.

Never Miss Twice

As I’ve written about previously, much of fitness (and of life as a whole) comes down to building good habits. But building new habits is tough. So I spend a lot of time thinking about and experimenting with hacks and techniques that might more reliably make new habits stick.

One technique that gets a lot of internet attention comes from Jerry Seinfeld. It’s called “Don’t Break the Chain,” and originates with an anecdote shared by software developer Brad Isaac:

Years ago when Seinfeld was a new television show, Jerry Seinfeld was still a touring comic. At the time, I was hanging around clubs doing open mic nights and trying to learn the ropes. One night I was in the club where Seinfeld was working, and before he went on stage, I saw my chance. I had to ask Seinfeld if he had any tips for a young comic. What he told me was something that would benefit me a lifetime…

He said the way to be a better comic was to create better jokes and the way to create better jokes was to write every day. But his advice was better than that. He had a gem of a leverage technique he used on himself and you can use it to motivate yourself—even when you don’t feel like it.

He revealed a unique calendar system he uses to pressure himself to write. Here’s how it works.

He told me to get a big wall calendar that has a whole year on one page and hang it on a prominent wall. The next step was to get a big red magic marker.

He said for each day that I do my task of writing, I get to put a big red X over that day. “After a few days you’ll have a chain. Just keep at it and the chain will grow longer every day. You’ll like seeing that chain, especially when you get a few weeks under your belt. Your only job next is to not break the chain.”

”Don’t break the chain,” he said again for emphasis.

That’s a great story. And the approach sounds easy enough. But having tested it out on myself and on Composite clients, it’s actually pretty much a miserable failure in real life.

Indeed, the problem with Don’t Break the Chain is that it reinforces the same all-or-nothing thinking that dooms most new habits more generally.

Here’s what typically happens when someone decides to start a new diet, for example:

For four or five days, they’re super gung-ho. They make perfect food choices, and bask in the glow of their newfound nutritional motivation.

And then, on the fifth day, they’re tired and it’s someone’s birthday at the office and there’s birthday cake. So they have the piece of cake.

And then they totally go off the rails.

Nutritionally, that single piece of birthday cake is pretty meaningless. But because we’re thinking all-or-nothing, because we’re trying not to break the chain, it feels like defeat. And since we’ve already lost, what’s the point? You might as well get some chips from the vending machine and a pint of ice cream with dinner and then maybe you’ll start again fresh next week with the diet and try to be more perfect that time.

In other words, it’s not the mistake that matters. It’s the spiral that too often follows it.

As a result, what actually works is a slightly different mantra: “Never Miss Twice.” (Hat-tip to James Clear for this one.)

You ate some birthday cake? Fine. But now your next meal has to be a healthy one.

You felt tired and it was raining so you skipped going to the gym? No problem. But tomorrow, you must go and make up the workout.

Never Miss Twice is the opposite of all-or-nothing, “Don’t Break the Chain” thinking. It acknowledges the difficulty of building new habits. It says, sure, you’re going to screw up; that’s how things go. But the crucial point, the reason why you’re going to succeed nonetheless, is that you’re not going to let that single mistake scuttle the whole plan. Any time you fall down, you’re going to get right back up. Any time you derail, you’re immediately going to get back on track.

You’re going to make mistakes, but you’re never going to make two in a row. Because, in the long term, those individual small misses don’t much matter. Instead, what really adds up are all of the good choices you get back to making after those misses. What matters is that you don’t let one small miss devolve to total disaster.

That’s all it takes. Never miss twice.


Here’s something I’ve been playing with lately: blocking my days into three big chunks. I have a Focus chunk from 6am to 12pm, a Buffer chunk from 12pm to 6pm, and then a Free chunk from 6pm to 11pm.

When I wake up, often while I’m still in bed, I immediately start working on my most important project. Literally, immediately. Somewhere in that chunk, I go to the bathroom, drink some coffee, and walk the dogs. But, otherwise, working on that project is the only thing I’m allowed to do.

At 12pm, unshowered and with glazed-over eyes, I usually walk the dogs again, head to the gym, shower, eat lunch, and then spend the balance of my Buffer block on all the other tasks I’d like to accomplish. Getting to inbox zero (in email, on my phone, with my paper in-basket), blogging, and banging out all the other work and personal tasks that aren’t part of my One Big Focus Project.

And then, at 6pm, I close my laptop, and try to spend the evening enjoying Jessie, friends, family and NYC.

Obviously, this only works because I have the luxury of working from home. But I’ve found that, at 6am, I’m basically still too asleep to creatively procrastinate; by the time my brain gears up all the way, I’m neck-deep in my most important stuff, and carried forward by the momentum. Whereas, before, when I’d try to work out and shower and walk the dogs and prepare for the day a bit before opening my laptop, I’d be in prime procrastinatory mode by 8:30 or 9:00am and manage to instead just tackle small unimportant tasks, telling myself I was clearing the deck for a deeper focus session later on that, on too many days, never seemed to actually arrive.

I’m not sure this would work for anyone else, but it sure as hell is working for me.