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.

Entrepreneur Time

For the last twenty years, I’ve been somewhat obsessed with time management, reading nearly everything I can find on the topic. By now, it’s rare that I find something that seems genuinely new. And it’s even rarer still when it’s something new that actually works.

Over the past year, I’ve heard several times about Dan Sullivan’s Strategic Coach, a business-development program for entrepreneurs. Most of Sullivan’s material seems better suited to solo entrepreneurs, or to entrepreneurs with small companies that grow out of consulting-style practices, like financial advisors or small financial advisory firms. And, frankly, it didn’t much impress me.

However, Sullivan does have a unique time management approach, which he calls the Entrepreneurial Time Management System. (Here’s one of several summaries.)

In short, the system involves breaking your week into three kinds of days: Free days, Focus days and Buffer days.

Free days are just that: days free from work. From midnight to midnight, there’s no business thinking or doing. No checking email, no managing crises, no work at all. While the first step is to make each weekend an inviolate pair of free days, Sullivan himself apparently shoots for 150 free days a year. Which, by my math, means he’s off every weekend, and takes a full week away two out of every three months. On free days, I power down my laptop and leave it in a drawer, turn off email notifications on my phone, and generally try to enjoy life.

Focus days, in turn, are those where you spend at least 80% of your time on things that meaningfully push your business forward. Email and other interruptions are still kept to a minimum, with your time instead in areas of your ‘personal genius’, the things that you do best that make the greatest contribution to your company’s bottom line. If I were running a gym, for example, I might focus on developing new programs, pushing new marketing initiatives, or interacting with clients.

Finally, there are Buffer days – your chance to get current on email and all the myriad small tasks (like accounting or staff training) that otherwise gum up the works and keep you from focusing uninterruptedly on the big-chunk work that really matters. By fire-walling that kind of work on Focus days (which seem to run on ‘maker’ time, and involve long stretches of, well, focus), you can then feel good about getting basically none of that big-picture work done on Buffer days, instead batching and banging through the detritus of your to-do list.

In fact, I’ve actually taken to keeping three different to-do lists, one for each kind of day. Museum exhibit I want to see: free day list. New content I need to develop: focus. Switching health insurance providers, consolidating old tax material files and sorting the contents of the overflowing junk drawer: all buffer.

Currently, I make Monday, Wednesday and Friday Focus days, and Buffer on Tuesday and Thursday. That leaves Saturday and Sunday Free, with the goal of taking at least a long weekend or two built by appending Friday (and potentially even Thursday) Free days a few times a month. (Conversely, a bunch of people seem to Buffer on Monday and Friday, with three Focus days from Tuesday through Thursday; I may shortly try that out.)

I’ve been following the approach for a few months, and have been most impressed thus far. Definitely worth a test run.

Mac Tools: Alfred

A recent study by Brainscape has shown that just learning keyboard shortcuts instead of mousing around the screen would save most computer users almost two full weeks of work time each year. I’m a big shortcut user (per my previous Gmail shortcuts post), though I also depend on a slew of free or cheap tools that similarly make my Mac far more pleasant and efficient. Over the next few weeks, I’ll be cataloguing the best of the bunch.

I spend that vast majority of my computer time in my web browser. But I also regularly dip into a number of other apps, as projects demand. Launching them the traditional way – going to the Finder, then opening the Applications folder, and double-clicking the app – is painfully slow. And Spotlight, the built in search functionality in OS X that also can launch apps, is underpowered and not much quicker.

Enter Alfred, a small app with a big impact. Once loaded, you can launch Alfred with a keystroke (by default, ‘command-space’), which loads an empty command bar, like this:

Screen Shot 2015-05-14 at 3.15.49 PM

Launching an app with Alfred is ridiculously easy. Just start typing the app’s name, then click enter once it appears:

Screen Shot 2015-05-14 at 3.16.26 PM

You can also use Alfred to quickly open files the same way:

Screen Shot 2015-05-14 at 3.17.05 PM

It works as a calculator, too. Just start typing an expression, and it automatically calculates the result:

Screen Shot 2015-05-14 at 3.18.12 PM

Alfred does far more than that, pulling info from contacts, managing iTunes, or saving prior cut-and-pastes from your clipboard. With custom workflows, you can add even more powerful behaviors – with just a few keystrokes, I can add a song on the current Spotify playlist to my saved files, for example.

In short, it’s a pretty deep rabbit hole. But in my experience, even if you never use it for anything more than app launcher, file-finder and quick calculator, it will already make your Mac wildly easier to use; enough so that you’ll chafe with irritation borrowing somebody else’s Mac that doesn’t have Alfred already enabled.

You can download Alfred free directly from creator Running with Crayons’ site.