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.


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.


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.)


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.


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.

Heart Felt

Perhaps due to my hacker roots, for more than a decade I’ve organized my life in a collection of text files. But when it comes to actually executing, I’ve discovered I’m far more productive working off a printed-out version of my Today.txt to-do list than I am with the same list on-screen.

For notes in meetings, too, I find paper and pen works better for me than an iPad or laptop. Much as for solo business strategy and planning sessions, where I tend to do my best work when I’m scrawling page after semi-legible page of ideas, mind-maps, outlines and diagrams. (Jess refers to this as my *Beautiful Mind* mode).

For years, I did my scribbling with blue Pilot G2 pens. Then about twelve months back, I switched abruptly to black Sharpie markers, usually writing on blank pieces of printer paper rather than yellow pad.

About three months ago, I ended up purchasing a variety pack of [Papermate Flair Felt-Tip Pens](http://www.amazon.com/Paper-Mate-Point-Guard-Assorted-8404452Pp/dp/B002R5AEIY/ref=sr_1_12?s=office-products&ie=UTF8&qid=1335062836&sr=1-12) to correct a document using the red pen. Though that pen was fine, and though the collection also included perfectly nice black and blue pens, I quickly found myself using only the green pen. I carried it in my pocket all day, using it at work, at home, to sign bills in restaurants.

A few times, I popped into Staples I happened to be passing by, hoping to find more green pens. But, in each case, the green was only available bundled in four-color packs. So, by now, a pile of unused black, blue and red Flairs sit unhappily in my desk, as I run through the ink in the couple of greens I own.

I don’t have a good explanation for why I like the green pen so much. It stands out? It’s easier on the eyes somehow than blue or back? It’s the color of money? It’s the logo color of Jess’ newly launched [Dobbin Clothing](http://www.dobbinclothing.com). (See what I did there, Jess?) But I do know that, soon, I need to start actually ordering these pens in twelve-packs online, because amassing unused other-colored felt-tips doesn’t seem like a particularly good long-term plan.

Kermit was right.


Somewhere over the past couple of years, Gmail solved spam. I’m not sure when it happened, precisely, but by now spam in my inbox is so rare that it actually catches me off guard. How did that get through?

Still, about six months back, I realized that nearly half of my email was what’s sometimes called ‘bacn': those notices, newsletters, updates and alerts somewhere between spam and the ‘ham’ of real, human-sent emails. Shipping notices from Amazon, connection requests on LinkedIn, investor updates, retweets on Twitter, bills due to ConEd, Time Warner and AT&T, server status pings, all piling up at alarming speed. And though I wanted to at least glance at all those emails, few were crucial, few warranted immediate reading or response.

Still, because of their sheer volume, those bacn bits quickly gummed up the works, making it harder to spot and corral the messages that really did deserve quick attention.

So, using Gmail’s filter system, I fixed the problem:

I created a label called “!Robots” (with the ‘bang’ / exclamation point to alphabetize first).

Then, over the course of a month or so, as any email came in that wasn’t a personalized message from a real person, I’d click the little arrow at the top right of the message, choose “Filter messages like this”, then choose “Skip the Inbox” and “Apply the Label: !Robots”.


Now, once every day or two, I head to the !Robots folder, and crank through the hundred or so messages that have inevitably accumulated. Most require nothing more than a quick glance. Others – say, an expiring domain – need a minute or two of action. Still, I can usually get through the folder in well under ten minutes.

And then, the rest of the time, when I check my email – whether in Gmail, in Sparrow, or on my iPhone – all I get is the good stuff. No weeding necessary.

Turns out, taking out the bacn has been as much of an improvement as taking out the spam.

5000, 4999, 4998, 4997…

I’ve been reading some kinesiology texts of late (yes, really), and stumbled across an interesting paper by Dr. Richard Schmidt [Motor Learning, 1988] about acquiring motor patterns through repetition.

Schmidt’s extensive research focused on the amount of practice necessary to learn a movement, to make it habit. A new pattern learned from scratch, he discovered, seemed to reliably take between 300 and 500 repetitions to become permanent. But new patterns learned to correct and replace an old, less efficient pattern instead consistently took between 3000 and 5000 repetitions – a literal order of magnitude difference.

I’ve thought about that recently as I’ve worked out, looking at the ways I move in basic exercises. But I’ve thought about it even more, looking at how I ‘move’ through the rest of my life.

Over the years of running companies, I’ve developed work habits, communications styles, and basic approaches to business. Most of those, on inspection, have served me very well. But a handful have not. And, indeed, I’ve increasingly noticed that I spend disproportionate amounts of time and energy undoing the problems cause by those handful of inefficient, bad patterns.

I’ve been focusing on correcting those patterns, replacing them with new, better, more efficient approaches. And, for the most part, I’ve been moving forward. But, of course, like with anything new, from time to time I misstep.

Before, I’d always believed the business self-help book saw that it takes 30 days to make a new behavior a habit. And, perhaps, in some cases, it does. But Schmidt’s research makes me think that time has nothing to do with it. Instead, it’s about volume of practice. And, in the case of re-learning something, it’s about a very, very large volume of practice.

Five thousand is an inordinate number of times to face a decision, and to make the right choice. In that context, those missteps seem inevitable. How can you do something new correctly five thousand times in a row?

And, just as important, in that context, it’s clearly only worth setting out for change when you’re ready to buckle down for a long-haul commitment, when you’re ready to start even knowing that you aren’t aren’t ‘done’, you aren’t finished thinking about your actions, until you’ve got things right again and again and again, three thousand to five thousand times.