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:

!from:j@outcap.com !category:forums !category:social !category:updates !category:promotions

For this one, you’ll need to replace my email (j@outcap.com) 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.


There may be nothing new under the sun (which is, itself, an observation from Ecclesiastes 1:9), but I’m still sometimes surprised by how modern a lot of ancient wisdom reads.

Consider this bit, from Epectitus’ The Art of Living, which could have been pulled from any of today’s bestselling self-help tomes:

“It’s time to stop being vague. If you wish to be an extraordinary person, if you wish to be wise, then you should explicitly identify the kind of person you aspire to become. If you have a daybook, write down who you’re trying to be, so that you can refer to this self-definition. Precisely describe the demeanor you want to adopt so that you may preserve it when you are by yourself or with other people.”

Keep Principles Principal

“As to methods there may be a million and then some, but principles are few. The man who grasps principles can successfully select his own methods. The man who tries methods, ignoring principles, is sure to have trouble.”
– Ralph Waldo Emerson


For years, I’ve been a fan of British productivity guru Mark Forster, sort of the UK equivalent of David Allen.

Unlike Allen, who’s pedantically determined to prove that his Getting Things Done system is The One True Way, Forster instead tends to play around with a variety of systems, tools and approaches, always searching out new ways of getting more important things done more easily.

From Forster, I picked up a writing trick that remains one of my most used tools: iterative expansion drafting.

The approach is simple. You start by jotting or typing out very fragmentary ideas, roughing out the piece. For the start of this blog post, it might be something like:

Following Mark Forster, UK David Allen.

Open to new ideas.

From Forster: iterative expansion.

Start with fragments, expand in passes.

Using this kind of framework, you can get thoughts out quickly, focus on what you want to say before you become mired in how you want to say it.

Then, after a break, you can come back and expand a bit:

For years, I’ve been a fan of Mark Forster. He’s sort of the UK’s answer to David Allen.

He’s open to new ideas, and tends to play around with a variety of tools and approaches.

One technique I took from Forster was the concept of successive iterative drafting.

The concept is simple: start with words and sentence fragments to get out the ideas, then return repeatedly to the document to expand and edit those fragments on subsequent passes.

From there, another pass or two yields a publishable post.

Without this approach, especially when creating dense work documents, I tend to spend an inordinate amount of time stuck drafting and re-drafting the first paragraph. But going iteratively, I can flesh out the spine of a two-thousand word white-paper in just a few minutes. And with each successive expansion, momentum carries me forward. I’m no longer forced to come up with ideas from scratch, not faced with the terror of the blank page. Instead, I’m simply adding to what already exists, and then phrasing and rephrasing in clearer, more readable ways.

At it’s core, successive iterative drafting is the concept of ‘shitty first drafts’ taken to its logical extreme: creating a draft so shitty, it barely even resembles writing, yet that still gets you an initial foothold from which to build.

For more on the approach (and a bunch of other excellent insights), check out Forster’s Do it Tomorrow. It’s the book I’ve gifted more than any other, and it’s certainly worth the read.

Can’t Stop Won’t Stop

As I mentioned in a prior post, I’ve been thinking a lot of late about Cal Newport’s excellent new book, Deep Work.  In it, Cal argues for the power of being able to focus hard on a single difficult task for an extended period of time.

Cal proposes a slew of ideas to help push towards that goal. But I’ve also been collecting tools that help nudge me in that direction. A lot of my own deep work is writing-related.  And for me, the hardest part of writing is just getting the words down in the first place.  So I need to force myself to bang out shitty first drafts.  Otherwise, I end up critiquing and editing, or stare at the blank screen.

Enter the excellent app Flowstate.  And the recently-launched free website The Most Dangerous Writing App. Both do the same simple yet powerful thing: they delete what you’ve written if you stop writing.

In either app, you choose a time frame for which you have to keep moving – five minutes, twenty.  And then you start typing. And you keep typing. You pour stuff out, good, bad or ugly. Because if you stop for more than five seconds, everything you’ve written fades away.  It disappears forever into the digital abyss.

It sounds a bit ridiculous. And, perhaps, it is. But it’s also just enough fire beneath my feet to keep me moving.  Sure, I need to edit the hell out of what I create. And it may not be your best bet for drafting poetry. But when I need to just get things on paper (or screen), to create a starting point, it’s an awesome tool.

Try them out, and see if living on the edge a bit helps you, too.

Entrepreneurial Time Management, Redux

About six months ago, I wrote about Dan Sullivan’s Entrepreneurial Time Management System. Since then, I’ve drifted away from the approach a handful of times. And, each time, like noticing attention drifting away from the breath while meditating and then refocusing on it, I’ve noted a drop in my work output, switched back to Sullivan’s approach, and been pleasantly surprised anew at both how much more I get done, and how much less stressed I feel.

Since the prior post, My only real change is a reorganization of when the different types of days fall in my average week. Instead of using Buffer days on Tuesday and Thursday to break up Monday, Wednesday and Friday Focus days, I now make Monday and Friday the Buffers, and do Focus work Tuesday-Thursday.

That uninterrupted stretch of really getting down to it seems to help hugely in terms of work output. And it dovetails well with a slew of additional suggestions from my friend Cal Newport’s great new book Deep Work, which is also worth a read.

As this is a Focus day, back to work!


For as long as I can remember, and across pretty much all of my thinking and writing tasks, I’ve been torn between using computers and using pen & paper.

By now, I keep my to-do list online (still in ToDoist), though I print it out each morning (from my trusty, highly-recommendable and cheap Brother HL-L2340DW), and work all day from the paper version.

I brainstorm and outline best on paper, but can draft and compose far faster on-screen.

And after recently converting the contents of a slew of separate Mac and iOS apps (Day One, Paprika, NVAlt, etc.) into a series of Evernote notebooks (as I’m now testing out using Evernote as my ‘everything bucket’), I’ve also taken to scanning all of my incoming mail, receipts, etc., into Evernote (primarily using their free Scannabale app), and lazily filing the physical papers by simply sticking all the stuff from a given month into a single file folder together (ie., “October ’15”).

Nonetheless, I also recently backed a Productivity Planner project on Kickstarter. Which, in turn, drove me to buy a Five Minute Journal, the prior project from the same designers.

I’m a pretty reliable journaler already, and in fact even previously used the outline of the Five Minute Journal questions as part of what I recorded daily in my digital journal file. But, as often turns out to be the case, there’s a difference between the experience in one medium versus the other. With the Five Minute Journal bedside, I’m more reliable at answering its short questions as the first thing I do when I wake up, and the last before I go to sleep.

So, consider a hard-copy Five Minute Journal – it seems to be making me happier, at least. And give some thought to which tools you use for your various pursuits. McLuhan may have overstated it, but if the message isn’t the medium, the medium still certainly very much matters.