Iterate

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!

Medium

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.

Soundscaped

Like many people, I tend to do my best works in ‘Goldilocks’ acoustic environments – not too quiet, not too loud, but just right. In college, for example, I never studied in the library, as I found the silence oppressive, and oddly distracting; I could never settle down to work. Conversely, I’ve long worked well in coffee shops, especially while listening to music through my own headphones just loud enough to somewhat muffle background noise.

But what kind of music? Anything with lyrics and I’m toast. As a trumpet player, most jazz, too, ends up sucking me into following the improvisations more than I intend. And any classical piece I’ve performed myself leads to my fingering the notes of the trumpet part along with the music.

So, instead, I tend to listen to a small number of albums, again and again. Keola Beemer’s White Mountain Journal, for example (much of which was used as score for Alexander Payne’s The Descendants), which iTunes tells me I’ve listened to north of 500 times.

Miraculously, I still like that album. As I still like the others on which I’ve been wearing off the grooves. But new, good choices are certainly a welcome change.

Which is why I was particularly happy to discover Focus@will, a music player serving up non-distracting background music while you work. You can choose from a slew of channels and energy levels, about a third of which I’m finding to be totally excellent for me.

Obviously, your mileage may vary. But if you, too, like to listen to music while you work, and would like to expand your listening repertoire to something less mind-numbing than albums on repeat, check it out. They have a 30 day free trial, so all you have to lose is an afternoon of sub-par productivity while you figure out if it’s a fit.

Todoist

For years and years, I managed all of my tasks, projects, goals and ideas using a handful of text files that I wrangled in the text editor BBEdit. It was nerdy and time-consuming, but also completely bespoke; the approach fit my workflow, and evolved over time as my working style did, too.

Along the way, I briefly tried out pretty much every task management software that existed. Some, like The Hit List or Omnifocus, I even stuck with for a couple of weeks. But, inevitably, I’d end up chafing under a program’s structure, or run into problems with its stability and data security, and return to my free-form text.

About six months ago, for reasons I can no longer recall, I decided to test out the online task management program Todoist. An extremely fast and fluid web app, it also boasted polished iPhone and iPad versions. So I dumped in my text files, and started using it. And then I kept using it. And using it. Two months in, I reverted to my text approach; after an hour, I started to feel that it was text, not Todoist, that fell short in comparison.

Six months later, I still use Todoist all day, ever day. If you haven’t tried it out, you should. (And sign up for the trial of the premium features; they make the app vastly more powerful, and are certainly worth the the $0.08 a day they cost if you decide to stick with it.)

Paradox

Recently, I stumbled across [Dance in a Year](http://danceinayear.com), an awesome single-page site from designer Karen Cheng. Atop the page, a video chronicles Karen’s dance skill progress over the course of a single year, from “embarrassing even alone in your room” to “ready to hit the club”.

Below the video, Karen shares her secret: practice every day, setting small goals along the way.

Or, in other words, the same advice that pretty much everyone ever gives on learning or doing anything at all.

Still, obvious isn’t the same as easy. Incremental progress is, by definition, slow. And daily hard work takes, well, daily hard work. So, instead, we Tweet and Facebook and Foursquare and Instagram our way through the day, chasing minor instant gratification, the sudden small changes that yield immediate inconsequential results.

And it seems we’re getting great at doing that! Problem is, it’s precisely the opposite of what it takes to actually be or do the things most of us really want out of life.

Backlog

And speaking of getting back on track:

In his excellent [*Do it Tomorrow*](http://amzn.com/0340909129), British time management guru Michael Forster observes that, on average, the number of incoming tasks, emails, whatever, that come into your life each day needs to line up with the number you can process, respond to, etc., over the course of that same average day. Otherwise, you end up progressively further and further behind with each day passing.

Once you’re behind, it’s increasingly tough to catch back up. It’s like bailing water out of a ship that’s already flooded. So Forster puts out an excellently elegant solution: declare a backlog, and move everything that’s come in prior to right this second to a separate list (or, for email, folder). Then focus, first, just on making sure you’re keeping up, day after day, with the new stuff as it comes in from here forward. After that, as time allows, then whittle away at the backlog.

Due to a slew of factors, which mostly boil down to me trying to juggle too much all at once, I realized earlier this week that I wasn’t even close to keeping up. My to-do list had hit 200 items – well beyond what I might hope to accomplish in a day, or even in a month. So, on Monday, I called shenanigans, and declared a backlog. I’m hitting new work as it comes in first, and slowly whittling away at those 200 items as the rest of my day allows.

If nothing else, it’s a good chance for me to watch carefully how much work comes in, and how much I can get back out, in a given day. If I can’t stay at inbox and task list zero, then I have to toss some commitments, or otherwise whittle away at the demands on my life.