Shooting Ourselves in the Foot with Bullets

by Ben Carter


We are out of control with our PowerPoints. 

 

As a group, lawyers are the worst presenters I know. As a group, lawyers should be the best. We make our livings telling stories to clients, judges, and juries. Yet, give us a Powerpoint and we will oppress an otherwise interesting and important story into a brutal deathmarch of text-laden slides worthy of the Jackson Administration. We read from our slides (which consist of the notes for our talk) until a woman in the audience begins to wish that the bullets on the screen were lodged somewhere in her prefrontal cortex.

It doesn’t have to be this way.

Never has it been this easy to give[1] a great presentation. Whether you use Microsoft PowerPoint or Apple’s Keynote, either program can quickly incorporate interesting images that capture a key concept. You can find these images online and save them to your computer in an instant. The fonts available to us are limitless.[2] Beautiful templates are prepared for us and baked into the software.

Never has it been this hard to give a great presentation. I have been traveling the state with the Kentucky Law Update series to talk about our enduring foreclosure crisis. I present after lunch. When I walk in the room during the break, I see the half-finished crosswords. I see the Amazon Kindle’s poking out of purses, the iPads filled with games and email. I know what I’m up against. The demands on our audiences’ attention have never been greater.

It has never been harder to get and keep an audience’s attention. I am here to tell you a hard truth: your deep knowledge and compelling series of bullet-pointed slides that explain everything so obviously and logically is not enough. Not even close. If you want your audience’s attention, you are going to have to rip it out of their iPad’s cold, dead hands.[3]

For trial attorneys like me, our livelihood depends on our ability to give a good presentation. Having someone’s attention is a precondition to persuasion. But, even if you are never going to set foot in a courtroom, you still need to know how to give a good presentation. You still have a stake in helping us all become better presenters.

There are 17,000 members of the Kentucky Bar Association. Each of us are required to gather 12.5 hours of Continuing Legal Education credit each year. We comply by sitting through lots of presentations. Multiply our membership by a 25-year career and collectively we will endure about 5,312,000 hours of presentations before we retire.[4]

That’s a lot of crummy presentations.

There are some basic things we can do to make our presentations instantaneously less awful. First, do whatever you need to do to keep your audience’s attention. If the only way you can do this is by butchering a chicken while talking about subrogation rights or ERISA plans, bring a tarp to make cleanup easier. Let’s stop pretending this isn’t a show and that we’re not, in part, ringleaders.

Next, adhere to Guy Kawasaki’s 10–20–30 Rule. No more than 10 slides. No more than 20 minutes. Nothing less than 30-point font on your slide. Look, your slides shouldn’t be your notes.[5] Your notes are your notes. After you create your crappy presentation that just reflect the main things you want to say, hit “Print”. Those are your notes. Congratulations. Now create your presentation with 10 words–one per slide that capture your points. Better yet, pick ten pictures that enliven the concepts and entertain while you use your notes. Your slides should be in conversation with your words, not an echo of them.

Third, get curious about how to make your presentations better. Read Presentation Zen by Garr Reynolds or Beyond Bullet Points by Cliff Atkinson.

Finally, it’s time we start expecting more of ourselves and our colleagues than dry marches through case law and statutes. Obviously, imparting substantive knowledge needs to happen, but it’s time to stop pretending it’s our audience’s job to already be interested in our topics and it’s their fault if they don’t give us their undivided attention. Their failure to pay attention is our failure to capture it. Be brutal in evaluations. Demand more. If a presentation wasn’t great, give suggestions to make it better. If the presenter just phoned it in, say so.

Presentations matter. They matter to colleagues, clients, opposing counsel, and juries. At a minimum, five million hours of smart people’s time is at stake. Don’t let a bad presenter waste another hour of yours.

Ben Carter is an associate at Morris and Player, PLLC, a firm for plaintiffs. He is a consultant to the Network Center for Community Change on issues surrounding foreclosure, tax liens, and vacant and abandoned property. He welcomes your thoughts and ideas: bwc@morrisplayer.com.


  1. When I say “give”, I mean it: a great presentation is a performance that stays with the audience. It is a gift.  ↩

  2. Please, stop using Calibri. When I see Calibri on the screen, the words I see are, “default.” As in: “The fact that this presentation is awful is default of the presenter.”  ↩

  3. I am aware that iPad’s do not technically have hearts and that they are, in fact, cold and dead already. You do not need to email me on this point.  ↩

  4. This doesn’t include all the time we spend in internal firm meetings that resemble the eye-popping scene from A Clockwork Orange ↩

  5. When was the last time you went to a movie and the screen was bifurcated: one side with the action and actors and the other side with a scrolling script? Exactly. Time to raise your game.  ↩


It's Time for Palau to Adopt a Bankruptcy Code

by Ben Carter


When I was in Palau in December, the Island Times was nice enough to publish this letter. 

Dear Palau,

Palau needs a bankruptcy code. I did not know that four years ago when I was working as a Public Defender for Palau, but I know it now. Too many Palauans live with crushing debt from which they will never recover. If Palau wants to provide those families any hope, it needs a bankruptcy code that offers Palauans a fresh start following financial devastation.

I have spent most of the last four years defending homeowners in Kentucky from foreclosure. That is, I have spent the last four years discussing debt and household finances with thousands of families.

While I was a Public Defender in Palau, I had the opportunity to take a few civil cases for debtors who owed either a store or another person a significant amount of money. Unfortunately, the only relief I could provide was trying to negotiate a complete repayment of those debts over the course of a number of years—often at usurious interest rates. These negotiated settlements were frustrating and unsettling to me personally because it meant that these debtors would have to struggle for years if not decades before saving for retirement, investing in their or their children’s education, starting a business.

Allowing people to file for bankruptcy wouldn’t just help individual Palauans who find themselves in over their head due to unemployment, medical setbacks, or poor financial management. Rather, there are at least five distinct benefits to providing Palauan individuals and businesses with a fresh start through bankruptcy.

  • Bankruptcy encourages economic development because it enables entrepreneurs to take risks with the understanding that if those risks don’t pay off, their lives and finances are not forever ruined.

  • Bankruptcy also encourages economic development by incentivizing investors and businesses to lend only to the most creditworthy entrepreneurs and customers.

  • A bankruptcy code would provide business partners with an orderly and predictable disposition of a failed business’s assets. This predictability reduces the cost of doing business and the cost of litigating the dissolution of the business.

  • Because the bankruptcy code provides parties with an orderly way of winding down businesses and discharging indebtedness, the court system may enjoy less litigation and fewer collections actions.

  • As I previously mentioned, Palauans deserve a fresh start. With a bankruptcy code, Palauans will know that getting laid off, encountering bad luck, or suffering through medical setbacks won’t forever plague their family’s chances at financial stability.

I hope you will not interpret this letter as the presumption of a haole thinking he knows what’s best for Palau. Having lived in Palau, I appreciate that Palauan bankruptcy will likely look very different than American bankruptcy—molded to respect tradition and the realities of life in Palau. But, I counseled plenty of hardworking Palauan families who will spend years struggling to pay back loans at unfair interest rates, struggling often with no realistic chance of ever actually catching up.

While I was in Palau, I failed to appreciate the benefits of having a bankruptcy code and failed to do anything to provide these families and individuals with the hope of a fresh start and the opportunity for financial stability. Now that I’m off-island, I look back and fear I missed an opportunity to leave a lasting impact in Palau and provide a lasting service to its people by advocating for passage of a bankruptcy code.

I am on-island over the holidays for a brief vacation and wanted to take this opportunity to urge the Palauan people to encourage their legislators to pass a bankruptcy code. To survive and thrive, Palauan families and businesses need the opportunity at a fresh start that bankruptcy promises.

I am happy to help this effort in whatever way I can from the United States. If you are interested in working on this issue, please contact me at ben [at] bencarterlaw [dot]com.

Sincerely,

Ben Carter


The Races I'm Watching

by Ben Carter


Alright, folks, here are the races I’ll be watching tonight and why. If you want to hang, I’ll be at The Silver Dollar with Judge Shake and crew.

19th District Senate

Morgan McGarvey’s a buddy of mine from law school and will make a damn good Senator. We’ll never end the war on young people without more young people making laws.

Commonwealth’s Attorney

My wife is an Assistant Commonwealth’s Attorney. So, yeah, I’m kind of interested in who will be her next boss.

Court of Appeals

I’m for Judge Shake[1]. Here’s why I’m supporting him. This race, unlike the others mentioned here, isn’t over with the primary. Judge Shake will need your help all the way through the November 6 general election. So, go give him some money or like him on Facebook or follow him on Twitter.

Lexington’s Third District Council Seat

I like Diane Lawless. I think she does a good job and trust her judgment. Stephanie Spires has by all accounts run a very good race. She is married to John Spires, a law school buddy of mine. So, I’ll be interested to see the outcome of that race. Diane and Stephanie will face each other (I expect) in the general election in November.

98th District House of Representatives

This is my home district back in Greenup County. Rep. Tanya Pullin[2] is facing a primary from Tyler Murphy. I think Tanya’s demonstrated ability to pass legislation through a Republican-controlled State Senate and her reputation for, you know, reading bills, working hard, and actually caring is enough to warrant her reelection. Plus, I just can’t forgive Tyler Murphy for being this guy at the 2008 Democratic National Convention.

So, those are the races I’ll be watching tonight. Good job for voting everybody.


  1. Full disclosure: I helped Judge Shake set up his website.  ↩

  2. Full disclosure: I helped Representative Pullin set up her website.  ↩


Typography for Lawyers: One Space, Double Spacing, and Other Good Ideas

by Ben Carter


This is an essay about typography.

What is typography? Basically, it’s how letters and words appear on the page, how individual words and chunks of text fit together. As lawyers, our livelihoods depend often on chunks of text. The thesis of this article is that small typographical improvements in your resumes, letters, briefs, and presentations can make a dramatic difference in your ability to effectively communicate and persuade.

Better typography improves your chances in mediations, in court, and in trial.

I need to make two points before I even get started. First, and perhaps already obviously, I am a nerd. How much of a nerd? I still own a 20-sided die. The best way to get me to corner you at a party is to mention in an offhanded way that you need to get a scanner (at which point, I will rhapsodize about the Fujitsu Scansnap 1500 for 20 minutes as the ice melts in your cocktail). As you will see, I’m the kind of nerd who can’t resist making a reference to Weird Al Yankovich’s cult classic UHF even in an article in which I hope to impress my peers.

I’m the kind of nerd that says, “Hell, yes!” when I discover that some typeface-designer-turned-lawyer has written a book about typography and the practice of law.[1] This is my second point: almost everything I have learned about typography I learned from Matthew Butterick and his excellent website, http://typographyforlawyers.com and book, Typography for Lawyers. Butterick is a Harvard-trained typeface designer and a graduate of the University of California Berkeley’s Boalt Hall. So, he’s kind of in his wheelhouse on the subject of typography for lawyers.

I recognize that not everyone has attained the same nerd heights as me and may not want to read an entire book about typography. This is an attempt at a summary. Still, I highly recommend getting the book. I refer to it each time I write a brief. It contains great examples of before and after improvements to business cards, resumes, correspondence, and legal briefs. Further, it contains detail that can only be captured in a book; Butterick explains the proper use of em dashes and en dashes and hyphens, the nuances of non-breaking spaces and non-breaking hyphens, the dark art of letter spacing. So, get the book.

Plaintiffs attorneys would do well to adopt better typographical practices now rather than later. Law schools across the country are using Butterick’s book as part of their legal writing curriculum. The federal clerks who are reading your briefs will know the best typographical practices and will judge you and your failure to adopt them. Further, as I mentioned above, better typography produces briefs, letters, and exhibits that are easier to read and therefore more likely to be read and understood.

Plaintiffs attorneys have a brief window in which adopting better typography will provide us with a subtle advantage. The defense bar will eventually adopt better typographical practices and then our failure to use them ourselves will disadvantage us and our clients.

So, let’s get started on improving our work product with better typography. I will begin with some practices that will improve all of your documents, including your briefs, and then discuss the impact of court rules regarding margins and line spacing in briefs.

Use One Space after Punctuation

Modern typographical best practices flow from an appreciation of a fact that has eluded many attorneys: we have computers now, not typewriters[2]. We learned to type (or our typing teachers learned to type) on typewriters that used a monospace font. That is, every letter, whether it’s a fat “m” or a skinny “i”, was stamped on a piece of metal that was the same width as all the other characters. Using two spaces after punctuation in a monospace font is acceptable (but even there, unnecessary). On computers, however, we are blessed with proportional fonts–fonts with varying letter widths. Using two spaces after a proportional font is a vestige of our days from the typewriter. It is, as Butterick says, “an obsolete habit”. As he says in his book and website:

Some top­ics in this book will involve dis­cre­tionary choices. Not this one. Always put exactly one space between sen­tences. Or more gen­er­ally: put exactly one space after any punc­tu­a­tion.

One space. Period.

Okay, with that sacred cow slaughtered, let’s move on…

Use Bold or Italic Type for Emphasis

Do not use underlining. Again, underlining is a vestige from our typewriter days when there simply was no other option but to use underlining to add emphasis. Bold type and italic type just weren’t available on typewriters. Bold and italic type are the typographical equivalent of the electronic unlocking mechanism on your car. When was the last time you actually unlocked your car with your key?

Use better tools: bold and italic typefaces are more elegant and less disruptive to the eye than underlined text.

Justify Your Text on the Left

There’s really not much to this rule except to say that studies have shown that left-justified text is easier to read than text that is justified on both sides. In a left-justified document, the reader’s eyes use the nonuniform breaks along the right side of the page as a subtle guide to find the beginning of the next line of text.

Unlike the two previous rules, you do not have to stop justifying your text on both sides if you don’t want to. Know that you are making your reader’s job more difficult, but justifying on both margins is still acceptable practice. If you justify on both sides, however, you are required to turn on hyphenation in your word processor. Hyphenation will help you avoid the unsightly gaps in text that can occur in documents justified on both sides. These gaps, like the double spaces after periods, are little tiny speed bumps for the reader’s eyes as they travel across the page.

Look, I should probably be explicit about this now that I’ve used the phrase “little tiny speed bumps for your reader’s eyes”: I write my briefs with the understanding that judges and their law clerks are drinking from the fire hose. Like little Joe Miller in UHF, judges and law clerks found the marble in the oatmeal and now their reward is to read tens of thousands of pages of lawyers’ briefs each year. My baseline assumption about my audience is that they are drowning and are looking for basically any reason to stop reading my brief. Given this assumption, a lot of “little tiny speed bumps” in my brief are a really big problem for me.

Use a Nice Font

Fonts are what most people think of when they hear the word “ typography”. I hope my ranting so far has given you a sense that fonts (technically, typefaces) are just a small element of good typography.

Consider investing in a nice font. Butterick has designed a typeface, Equity, to meet the special needs of attorneys. It is polished, tight, and its italic is beautiful. Seriously, I find myself trying to find reasons to italicize words when writing with Equity. It’s available for purchase on his website. He also has recommendations for replacements for your Times New Roman and other common system fonts that are preinstalled on your computer and make your work look like everyone else’s work.

Avoid All Caps

Many attorneys rely on ALL CAPS as a way to emphasize their most important points and in the headings of their briefs. This is not a useful practice. ALL CAPS IS ACTUALLY HARDER TO READ than regular text. Butterick allows for a single line of all caps text, but no more. Personally, I try to avoid it whenever possible.

A bolded, underlined, all caps heading is just an invitation to your reader to skip past it.

On a related note, if you have a case which involves the question of whether a provision in a contract is clear and conspicuous, Butterick is available to serve as an expert witness. I think his services would be especially useful in consumer cases which involve contracts that contain paragraph upon paragraph upon paragraph of all caps text. The science is in: this text is difficult to read.


Every court promulgates rules regarding typography. These rules are designed to promote fairness, uniformity, and legibility by forbidding attorneys from engaging in the worst typographical practices in an effort to squeeze more words onto a page. These rules have their most dramatic impact on line length (margin rules) and line spacing (the requirement that the lines be double-spaced).

Shorten Your Lines Outside of Briefs

“Shorter lines are easier to read than longer lines,” says Butterick. Ideally, your line will be between 45 and 90 characters, including spaces. Most courts in Kentucky require one-inch margins on both the left and right. (The appellate courts require 1 1/2" margins on the left.) At these margins, your 12-pt Times New Roman line is going to have more characters than the recommended maximum of ninety. Outside of lobbying for a rule change, there’s nothing you can do.

Move on to something you can fix: your line lengths in your letters, interoffice memorandum, and presentations. For me, shortening my line lengths was a revelation; this small change led to an immediate improvement in the look and readability of my letters.

Use True Double Spacing for Better Briefs

The ideal line spacing is 120–145% of your font size. That is, if you are using a 12-point font, you should set your line spacing between 14.4 and 17.4. Personally, for my out-of-court documents, I use 15-point spacing. It provides a little more space between the lines than the “single spacing” setting (which makes words look cramped and is difficult to read).

Most courts require us to double space our briefs.[3] CR 76.12(4)(a)(ii) requires us to use “black type no smaller than 12 point” and typing that is “double spaced and clearly readable.” The court’s requirement to double space your briefs does not mean, however, that you just go into Microsoft Word and pound the “double space” button. True double spacing for a 12-point font means setting your line spacing at “Exactly” 24 points. Using Microsoft Word’s default “double space” will give you line spacing greater than 24 points–about 15% greater, in fact. This translates to having 2–3 fewer lines on a 8 1/2“ x 11” page.

In other words, if you are using Microsoft Word’s default “double space” setting for your pleadings, you are hurting yourself in two ways: 1) you are making your document less legible by putting more space than ideal between your lines and 2) you are making your document longer than it needs to be. Because our courts set maximum page limits (rather than word limits), this means you are giving yourself (and your client) fewer words to explain your position than you would otherwise have available to you.

How many times have you been on page twenty-six and need to slim a brief down to twenty-five pages? True double spacing will give you more words and those words will look better on the page.

There: I just gave you a way to be more verbose than you already are. For that and for all the other typographical wisdom (cribbed entirely from Matthew Butterick), you’re welcome.

Sometimes it pays to know nerds.


  1. The only other lawyer I knew personally that had read Typography for Lawyers and cared about this stuff at all was Finis Price. I miss that guy.  ↩

  2. For anyone reading this still using a typewriter: you need help this article cannot provide. Please stop reading.  ↩

  3. I’ve looked through Jefferson County’s local rules and can’t find a double-spacing requirement anywhere. Nonetheless, I think the court would look askance at anything not double-spaced.  ↩


Why I Support Judge Shake for Kentucky Court of Appeals

by Ben Carter


The reality of judicial races is that people who work outside our legal system feel ill-equipped to cast an informed ballot. I'm often asked by my non-lawyer friends who they should vote for in judicial races. In the Court of Appeals race in Jefferson County, I suggest a vote for Judge Jim Shake

Judge Shake is a smart, pragmatic judge that works hard and takes risks to ensure that everyone has access to the court system and that the courts are solving problems. I know. In 2009, as the Chief Judge of the Jefferson Circuit Court, Judge Shake worked with advocates for homeowners (I was an attorney for the Legal Aid Society at the time), bank attorneys, community groups, and the court system to create the Foreclosure Conciliation Project. With the FCP, Jefferson County became the first court system in the state to attempt to address the exploding numbers of foreclosures in our community.

As part of the project, Judge Shake ensured that each homeowner facing foreclosure received credible, timely information about alternatives to foreclosure and steps to take to avoid foreclosure. The FCP provided homeowners with outreach, housing counseling, legal representation, and an opportunity to meet with their banks to pursue these alternatives. Hundreds of homeowners saved their home through the process that Judge Shake created and the lessons we learned in Jefferson County have influenced similar programs across the state.

Judge Shake has been a judge for 19 years. He knows the immense impact the courts have on Kentuckian's lives. The courts impact lives not just in individual cases, but also in the processes and procedures they build to solve emerging problems like the foreclosure crisis. I'm supporting Judge Shake because he has shown the willingness and ability to solve problems—big and small—as a judge.


In 2012, Email Doesn't Have to Suck

by Ben Carter


We do not ride on the railroad; it rides upon us. Did you ever think what those [ties] are that underlie the railroad? Each one is a man, an Irishman, or a Yankee man. The rails are laid on them, and they are covered with sand, and the cars run smoothly over them.

—Henry David Thoreau, Walden

Email is the modern railroad. For many, a convenient tool to communicate with loved ones turned quickly into a primary source of nagging oppression and dread. We have stopped riding it and it now rides on us.

It doesn’t have to be this way.

Last week, I wrote (probably too much) about my big edit. I had initially anticipated including a section on email because email contributes more to our collective sense that we are “drowning in clutter” than any other aspect of life in the developed world in 2012. More than cabinets full of paperwork, more than overflowing bookshelves, sports equipment, computer cables. More than anything else, email clutters our existence.

But, I couldn’t really make the subject fit into that essay and decided that email is worth its own, separate discussion anyway.

Developing a better relationship with email and cultivating a quieter inbox is probably the single best thing you can do to get a quieter mental state. [1]

Later in this essay, I’m going to offer a few tips, tricks, and tools for you to consider using to process the flood of emails and quiet your inbox. However, and this is important nothing—no application or service—will save you if you do not first develop a healthier perspective about your email and redefine your relationship to it.

For this work, this work of deciding how much authority you are willing to cede to your inbox over your time and attention, there’s nobody better than Merlin Mann. Merlin chafes when labeled as a “productivity guru” and for good reason.

As Merlin explains in his foreword to David Sparks’s excellent book, iPad at Work, “productivity gurus” often profit by peddling the false notion that what you really need is a better way to work. Better tools, better processes, etc., etc., etc. That is, they convince you that if you just had this one thing, THEN you’d be able to write that novel. This is not true. What you need to create a novel is not a better word processor but the willingness to sit your ass down and type. And suck. And come back again tomorrow.

What we all really need to do is to work hard at the things we love and occasionally—only occasionally—look up from that work, look around briefly, see if there’s anything available that will help us work better, and then get back to work.

I hope this essay will be one of the only articles you take time to read about email because, frankly, you shouldn’t have time to read many more. (So, I’ll try to make this one good.)

With all this said, Merlin’s hour-long talk at Google about email, called Inbox Zero, is now canonical and required viewing for anyone wanting to develop a healthier relationship with their email (and, really, anything that is going to consistently demand more of your time and attention than it probably deserves).

Because our time is short, I will only say that I think it’s worth your time to decide how much of your life you are willing to give to email. And, I think it’s worth a small investment of time to get marginally better at email. (Seriously, stop reading this and watch Merilin’s talk.)

Okay, let’s talk about some basic moves you can make that are going to improve your email game significantly and give you a quieter inbox.

1) Probably the best way to get a quieter inbox is to get fewer emails. I’ll admit it: I am borderline crazy about not signing up to receive email from companies or organizations. And, if I accidentally do sign up and emails start hitting my inbox, I click the “unsubscribe” link at the bottom of the email[2] almost every time. If the sender doesn’t have a heartbeat, it’s probably not landing in my inbox.

Sometimes, giving an email address is unavoidable. Consider setting up a dummy email address for all the dummies who want your email address. One that you use only for commercial transactions.

On the topic of getting fewer emails…let’s talk about spam. Look, it’s 2012. We’ve beaten spam. If you’re still using an email provider that allows spam through, that’s on you. I run all of my email addresses through my gmail account. Yes, Google is getting creepier, but I’m willing to put up with creepy in exchange for massive storage and bombproof spam filtering. For a less creepy service, check out fastmail.com.

I want to go through a few more basic moves you can make, but keep reading to the end for some ninja moves to get a quieter inbox.

2) Turn notifications off in your email client. Whether this is Microsoft Outlook, Apple’s mail.app, Sparrow, a web-based email provider, whatever.

Turn.

Off.

Notifications.

Allowing the distraction of a ding or a pop-up is inexcusable. Your work is important. Stop allowing email to interrupt it.[3]

3) Use rule-based filtering to send listserv emails directly to a separate folder or folders. That stuff does not need to be in your inbox.

4) Develop a task management system[4] that will allow you to read an email, determine the action you need to take as a result of that email, place that action in the task management system, and archive that email. In other words (and stated negatively, which I know is sort of frowned upon by psychologists if you hope to change a person’s behavior) STOP USING YOUR INBOX AS A “TO DO” LIST. If I have to explain to you why this is insanity, you clearly have not taken my advice to watch Merlin’s talk about email and do not deserve further explanation from me.

Regarding archiving: I wrote at length in the essay about my big edit about how any taxonomy you create in life should be commensurate with the likelihood that you will need to retrieve information from the classification system and how quickly you will need to retrieve that information. And here’s the thing, in 2012 search functionality in every major email client is so good that my classification system consists exclusively of a folder called “Archive”. That is, the only question I need to answer before I can decide where an email goes is, “Is it possible I will need this email again someday?” If the answer is “Yes”, it goes in my archive folder. If the answer is “No”, I press “Delete”. (If you use Apple's Mail.app and decide you want/need a higher level of organization than an "Archive" folder, consider MailTags as a solution. Combining MailTags with the developer's Mail Act-On program supercharges Apple's Mail.app.) 

Done.

I’ve had this system in place for over four years and have never been unable to find an email (or thread of emails) I needed within 30 seconds of searching. I know people—smart people—who devote their valuable—very valuable—time and attention to dragging and dropping individual emails into a complex taxonomy of folders and subfolders and sub-subfolders. This is madness. Stop the madness.

5) Designate specific times of the day to read and process email. Spend the rest of your time on actual work[5]. If you fail to corral email into specific, designated chunks of time, it has a way of creeping into the rest of your day and taking over. You know what I’m talking about. I have to admit, I’m not as good at this as I want to be. Yet.

Notice that I’m not saying, “ Only check email when you arrive at the office and before you leave work”. Or, “ Check email at the top and bottom of every hour.” Your job is different than my job and you have to determine for yourself the maximum amount of time you can spend away from email and not get fired. That’s why they pay you the big bucks. For me, depending on the day, the maximum time away from email is probably once every hour.[6] If you have the kind of job where you need to be constantly checking email, maybe consider finding another job because that’s no way to live.

Consider adopting the Pomodoro Technique to avoid the temptation to dip into your email.

Ninja Moves

As I’ve already explained, the real ninja move is deciding that email will not dominate your life. The real ninja move is putting email in proper perspective and in its proper place given our ultimate job as human beings to love one another and make life better for everyone.

How much is our constant attention to email promoting that mission?

Within the understanding that no service or system will develop the proper perspective on email for you, I have recently discovered a couple services that are worth mentioning because of how well they work to quiet your inbox.

I started using unroll.me a few months ago as a way to unsubscribe from tons and tons of email lists to which I had become inadvertently subscribed. You give them your email address, they look at your emails, determine what companies and organizations are sending you emails, and provide an easy interface from which you can massively unsubscribe. Then, for the lists to which you decide to remain subscribed, unroll.me consolidates each one of those individual emails you would have received into one daily email digest.

Niiiiiice.

The service is free.

About a month ago, I heard about a service called SaneBox from Brett Terpstra (Terp! Stra!) on Mac Power Users. Basically, SaneBox works by only allowing email into your inbox that it thinks is important. Everything else goes into a folder called “SaneLater” for you to check at your leisure. Out of the gate, the algorithm SaneBox has developed works beautifully to determine an email’s importance. During the first two weeks, I think I needed to move one email from the SaneLater folder to my Inbox. (And, SaneBox watches these actions and refines its algorithm based on how you treat your email.)

SaneBox is a great service. It dramatically reduces the incoming traffic to my inbox so that I can process my inbox (when I check it) much more quickly and get back to work. Then, when I check my SaneLater folder (once a day or so), I can quickly scan to see what happened on Facebook and Twitter, see if an email got put in the SaneLater folder that shouldn’t have (it didn’t), and check my unroll.me digest of mass-mailing emails. This digest lands directly in my SaneLater folder; Unroll.me within SaneBox twice removes me from most of email’s bullshittiest bullshit.

SaneBox charges $4.95 per month for its service.[7]

 

It’s worth it.

I know, you are so used to not paying for things on the internet, but here are two things to consider. First, services that you don’t pay for with money, you pay for with your eyes. If you’re not the customer, you’re the product and the company’s business model likely involves advertising to you (Google and Facebook) or monetizing you (Instagram). Second, businesses that don’t make money don’t stay in business. Services that you don’t pay for can go away. Fast. I do not want SaneBox to go away. It has dramatically improved my email game.

*   *   *   *   *

Email is awesome. I’m glad I grew up in a time before email and lived until a time when email became commonplace because we truly live in a miraculous age. At the beginning of email, it was a miracle. I specifically remember sitting in a computer lab in Madrid, Spain in 1997, emailing my family, and staring in slack-jawed awe at Hotmail. Then, email became a burden and a bane because we hadn’t developed the tools—psychological and technological—to relate to email in a way that wasn’t insane.

That is no longer the case.

It’s 2012: email can be a miracle again.


  1. Outside of, you know, actually cultivating mindfulness through a dedicated meditation practice. But, that sounds like a lot of work.  ↩

  2. Quickly, let me say this about people and organizations who send out mass emails without offering the recipients a way to unsubscribe: they are awful people and awfuler organizations. When I receive a mass email that does not contain a way to unsubscribe, I usually respond with a TextExpander snippet that allows me to type “;unsubscribe” that then expands to read: “Please unsubscribe me from this list. You really should put an ”unsubscribe“ link on any emails you are sending to an email list. Just a suggestion: You may want to look into a MailChimp account for sending out email blasts. It’s free for lists of up to 2,000 people and you can send up to 12,000 emails a month. Good templates, too.” I sort of think it’s everybody’s job to make everybody else a little better, or at least a little more considerate, about email.  ↩

  3. This directive includes removing the red badge that screams at you from your iPhone’s mail app: “You’ve got four messages waiting on you! What are you doing enjoying lunch??? YOU’VE GOT MAIL!” I’ve turned off the badge and I’ve turned off “push” behavior on my phone so that my phone is only checking for mail when I go to the mail app.  ↩

  4. Again (as I explained in My Big Edit, I use OmniFocus for a task management system, but that’s because I’m awesome. You’ve got to get a system that works for you. Reading Getting Things Done is not a bad place to start.  ↩

  5. Yes, I am aware that for many of us, email is actual work. That is, part of our jobs is to check and respond to email. But, unless you work in customer service as an online customer service representative, it’s probably not your entire job.  ↩

  6. In reality, it is probably much longer than this. Very rarely is something so urgent that it needs my attention now rather than perhaps three to four hours from now.  ↩

  7. Full disclosure: if you use any of the SaneBox links in the body of this post to subscribe to the service, I get a small credit for referring you to the service. Like, 5 bucks. So, just assuage concerns that I'm recommending this service because I want some sort of kickback rather than recommending it because it is awesome and it works, here's a link to SaneBox that won't give me a referral credit.  ↩


The Golden Envelope

by Ben Carter


IMG 2964

I recently wrote about my “Big Edit”, during which I had the occasion to send many of my closest friends a lot of mail. Which meant I got to use a lot of 6“ x 9” envelopes.

Which made me very happy. I love the 6“ x 9” envelope.

“Oh my God, is he really going to write about how much he loves a goddamn envelope?”

Yes, yes he is.

My affection for the six-by-nine is both aesthetic and pragmatic.

The six-by-nine is a great size. Closest to the proportions of a golden rectangle than any other envelope[1].

It’s not just the proportions that are right with the six-by-nine. The color is right, too. Manila looks so much better sitting on a desk than the bleached white of other envelopes.

If you use a six-by-nine with an 8–1/2“ x 11” sheet of paper, you don’t have to wonder where to fold it. Just fold it in half. Not so with the standard envelope—with that, you’re always having to guess in thirds.

Only needing to fold once has pecuniary benefits, as well. The USPS considers any envelope up to 6–1/8“ x 11–1/2” to be a “letter.” That’s right, you can send this larger, better-looking envelope for the same price as the ubiquitous #10 envelope (9–1/2“ x 4–1/8”).

The USPS places both weight and thickness limitations on that “letter designation”. If a letter is more than 1/4“ thick, you will be paying at the ”flat“ rate rather than the ”letter" rate. That is, you may have to pay more postage on a letter in a standard envelope than in a six-by-nine simply because it is 50% thicker.

You can send more stuff for less in a six-by-nine.

The six-by-nine also sends the right message to the recipient. It’s not an often-used envelope. The #10 and the 9“ x 11” are so quotidian, so business-like. I’m a lawyer who prosecutes cases for people who have been injured by someone else’s negligence or bad faith. I pursue negligent lawyers, insurance companies, and predatory businesses. Motions to dismiss my clients’ claims arrive in 9“ x 11” envelopes. Bills and notices from Medicare arrive in #10s.

You’ll never get a bill in a six-by-nine.

What’s inside of a six-by-nine is a) casual enough for a fold but b) substantial enough for a six-by-nine.

Before you run out and buy a bunch of six-by-nines, here’s some practical advice: buy the ones without the prongs. This is my only caveat. The USPS requires the sender of any envelope containing prongs to either a) remove the prongs (this is the preferred resolution of the prong-issue) or b) tape the prongs down. If you have the option (and you do, buy the prongless six-by. Your local postal worker’s fingers thank you.

So, what’s not to love? The six-by looks better and is more practical, more fun, and easier to use.

Think about it. You’ll come around.


  1. For an envelope with the shorter side of six inches to conform to the proportions of a golden rectangle, the longer side would need to be about 9.7 inches.  ↩