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, 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.  ↩

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

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, Sparrow, a web-based email provider, whatever.




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 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 


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 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, consolidates each one of those individual emails you would have received into one daily email digest.


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 digest of mass-mailing emails. This digest lands directly in my SaneLater folder; 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.  ↩

My Big Edit: A Lightening

by Ben Carter

Here’s how all this started: it was time to move my summer clothes on to my shelves and my winter sweaters into the plastic tubs where they live six months of the year.

I looked at my sweaters and all my t-shirts and all my button-down shirts and thought, “You know, I’m really not using 75% of this stuff.” So, I started putting some my clothes in boxes. Boxes to donate and boxes to throw away. I had lots of boxes. Good boxes. In fact, in my basement I had a whole shelf of boxes inside of boxes inside of boxes.

And here’s the thing: I did a really good job.

Suddenly, all the t-shirts that I owned fit on one shelf; only the sweaters that I actually wore this year went into a plastic tub for next year. I threw away socks that I never wore, underwear that was well past their expiration date. Well past. I will spare you the details.

And I looked up from my closet—my manageable and useful closet filled with only clothes I use and love—and looked around my basement (that’s right, I dress in my basement next to my lawnmower) and saw piles of stuff that I just never was going to use. A bike that came with the house that is too big for Erin and too small (and too girly) for me, supplies for applying plaster to my home’s walls, a mosquito net from my time in Thailand. Once my clothes shelves were clean, they stood in high relief against the clutter surrounding them.

I walked upstairs, and saw books that I was never going to read, LPs I never listened to, two file cabinets full of files on which I rarely relied or needed, and in the guest bedroom another five shelves of the detritus of my life: notes passed to me in middle school, postcards I sent my family from Europe, 20 different forms of ID [1], hundreds of letters written to me while I was at summer camp, while I was at Davidson, while I was in Ghana or Peru or Thailand. Maps. Maps of bicycling routes in Europe. Trains schedules from China. Legal pads filled with notes I took during client meetings and during trials as one of two Public Defenders in Palau.

*  *  *

I have never had a good memory. People who know me know I have a hard time holding onto even the thread of a conversation, much less remembering a moment earlier that week, last month, last year.

I realized this truth about myself as a teenager and began collecting scraps of paper, notes, ticket stubs, business cards, brochures, photographs in an attempt to create a more reliable record of my life; one that was not contingent upon the tenuous biochemistry of my faulty noggin. In my house I have a fireproof box, filled with pocket-size notebooks containing whole conversations, grocery lists, poems, and ideas for poems. If it’s not written down, it didn’t happen. I think FDR said that.

About this time (by which I mean “about the time I began recognizing just how much stuff was in my house that no longer had any utility”), I was listening to one of my nerdy podcasts when my favorite nerdy podcaster of them all, Merlin Mann, started talking about clutter. On S1E56 of his podcast, Back to Work, he spoke knowingly (and quickly) about the psychological weight of clutter, the burden of our things. He mentioned a book called, It’s All Too Much, by Peter Walsh.

Then, three or four days later, I was staining my deck and listening to Andy Ihnatko on his podcast (also on the mighty 5by5 network, also co-hosted by my internet pal, Dan Benjamin), The Ihnatko Almanac. I listen to a lot of nerdy podcasts. On this particular episode, Andy spoke eloquently and thoughtfully about the importance of conducting what he called “The Big Edit”. Andy describes the process of going through your crib and “touching everything you own.” The idea of editing your stuff immediately appealed to me and provides the right frame for thinking about the work.

If you’re considering attempting your own Big Edit, I recommend you listen to Merlin and Andy’s podcasts and read Peter Walsh’s book before you start.

What these guys—Merlin, Peter, and Andy—will tell you (and what I’m about to tell you) is not the “tips and tricks” of organizing—any joker/charlatan can tell you what kind of plastic tub to buy for your handbags. (This joker will tell you some of the logistics that worked for me later in this essay).

Instead, what these guys will help you understand is that facing your stuff is an intensely emotional experience. Digging through old letters, organizing photographs: these activities will require you to confront your relationship with your parents, with past lovers, with old friends who with the passage of time are no longer friends. During a Big Edit you will confront the reality of the distance now gulfing you and the people you used to love. Whether you have children or not, you will have to confront the ghosts of people you don’t know yet, may never know. Maybe you keep things around because you expect your children to care—one day—about your life.

Maybe digging through your things will make you wonder whether anyone will ever care about your life, your things. The things you love.

And suddenly I am reminded, specifically and clearly, of a poem I once heard Garrison Keillor read on The Writer’s Almanac by Jim Moore:

It Is Not the Fact That I Will Die That I Mind[2]

We can feel about our things the way Jim Moore feels about his family, about his oak tree. We love these things and people so dearly. So palpably. We fear that if we let go of the pitcher our grandmother left behind, we will be letting go of our grandmother. And we fear that no one knows how to love the way we do. Facing our things, we are forced to confront the very real possibility that no one will ever care for the things in our lives and the events those things represent the way we do. It’s just brutal.

If you’re like me, you done some pretty dumb stuff in the past. A Big Edit will require you to remember past harms you’ve inflicted and passed harms that were inflicted upon you.

All of this is to say that excavating the dark, cluttered pockets of your house means excavating the dark, cluttered spaces of your psyche. I think this is the primary driver of clutter: the fear of addressing the emotions attached to our stuff. We know that if we had a map of our houses and our minds, the cluttered areas in both would be marked: “There Be Dragons.”

A Big Edit doesn’t just dredge the past; it also demands an evaluation of the present and future. It requires the editor to acknowledge the true nature of her life as she currently lives it.

It became very clear to me very quickly that I no longer have international adventures the way I once did and that I do not have the time or inclination to listen to the 250 LPs I own. I thought I was a guy who likes music; turns out, I would rather listen to nerdy podcasts.

During the Big Edit, you will have to confront your own mortality. For me, this happened at my bookshelf. Gazing over the spines of unread books and read books I’d hoped to read again, I began to be able to say to myself, “I’m never going to read that book.”

If I had all the time in the world, maybe. But I do not have all the time world. Not even close.

So, confronting your stuff is hard. There’s a reason it’s called baggage.


The Big Edit is not just morose morbidity. If it were, we’d probably all be better off pursuing self immolation. I have to admit: I really enjoy the process of “touching everything I own” and deciding what needs to happen to it. The Big Edit is an opportunity to acknowledge and appreciate the past, take an inventory (mostly psychological but, yes, also physical) of your present life, and plan for the future you want to inhabit.

More than anything, it’s an opportunity to say, “I’m moving on.” I find “moving on” to be a useful mantra during this process.

In some ways, a Big Edit is a process of allowing the past to weaken in its grip upon you. I kept hundreds of notes and letters from friends, from girlfriends, from girls that I wanted to be my girlfriends, from teachers, from teachers that I wanted to be my girlfriends, from Wendell Berry, and from my granny. Reading over these notes and letters reminded me of how earnestly I approached these relationships, how involved my emotions were. Revisiting those moments, many now over a decade old, I don’t view those emotions as silly or misplaced, but I can recognize—now—their impermanence. The emotions that were so earnest, so important were, after all, fleeting. That’s a lesson worth remembering.

As I told a friend:

One of the best gifts I gained from looking at, literally, every single piece of paper I ever collected, is a sense of levity, lightness, distance from my present-day emotions. Reviewing all of these documents—tokens of deeply held beliefs, deeply felt emotions—gives me faith that today's emotions, whether good or bad (usually, mostly good), will also fade. It's almost liberating. I'm using religious words not unpurposefully.

I think the word I was looking for was "enlightening". 

I’m thirty-three now, but I haven’t stopped having emotions; it’s useful to know that one day I’ll be able to enjoy the same distance from present-day events as I now enjoy from the events captured on notes scribbled and passed in between classes at Russell High School.

A Big Edit is primarily a psychological exercise. It is worth investing some time before you begin to get into the right state of mind before you begin because once you find it, the rest of the work is a joy.

*  *  *

Okay, I want to talk high-level logistics quickly, and then move on to specific problems and how I solve them. There are essentially 4 things that can happen with any piece of your stuff. You can:

  1. Trash it
  2. Donate it
  3. Sell it
  4. Or keep it.

So, as you go through your things, you’ll want three bins in which to toss things (trash, donations, sales). These should be large bins.

Let’s talk about each of these for a moment.

“Trash It”

This ought to be your default mindset. That is, if you’re going to decide to do anything with a thing but trash it, you’ve got to have a reason: because you either love it or use it. Hopefully, both.

It’s called a Big Edit.

“Donate It”

Donating something is a useful compromise between trashing an item in keeping it in my house. The story I tell myself when I’m donating an item is that I am helping that item achieve it’s highest in best purpose by allowing someone else to put it to better use then it’s currently serving in my house. One caveat: don’t donate junk. If you don’t have a use for it, or it’s not in good enough condition for you to use it, ask yourself whether it’s likely this item will be purchased. Goodwills and other charities get plenty of junk and borderline junk. They don’t need yours. Just trash it.

Speaking of charities, my church is having a yard sale on June 16. We would be happy to receive your non-junk donations in the days leading up to our rain or shine yard sale. Just contact me for more info. In the alternative, you’re welcome to come and by some of our non-junk stuff on June 16.

Final point: make sure to keep track of your donations and document those donations as charitable gifts. Your future self will thank you for the tax deduction.

“Sell It”

After you’ve decided to sell an item, I want you ask yourself a question: “Really?”

Is it really worth your time to list your George Foreman Grill on Craigslist and meet some sketchy sketcherton at a coffee shop for 5 bucks? If the answer is yes, go for it. But, I would encourage you to use your limited time and energy towards finishing the big edit and moving on.

If you are determined to sell something, obviously eBay and Craigslist are resources you want to explore. Consignment shops are an efficient way to sell clothes and jewelry. For electronics, I recommend

Think long and hard about trying to sell your books. It’s rarely worth the effort. Recent editions of expensive textbooks? Maybe. Check out for going rates of the books. Your dog-eared copy of One Hundred Years of Solitude? Nope. A resource I’ve used in the past is This service allows you to list books you are willing to ship (at your expense) to other bookmoochers and you can search for books you want to read and then mooch them for free from other book moochers.

“Keep It”

Anything you’re not trashing, donating, or selling, you’re keeping. This is not an organization essay. I’m not going to tell you how to organize the stuff you keep. This is an essay about how to keep less stuff.

A final note on big picture logistics: as you dig through your crap, the litter box of your life, you will invariably find clothes that need to be taken to the dry cleaner, buttons that need to be sewn back onto jackets. You will discover that the cat peed on your mop and that you need a new one. You will need to keep a list of all the things that need getting done sometime later.

I use OmniFocus, but that’s because I’m awesome. If you want to use pencil and paper, that works, too.

My only other advice is to create contexts for the things you need to do. For example, keep all of the errands you need to run in a list called “Errands”. Keep all the things you need to discuss with your spouse in a list titled “Shithead”. Group calls under “Calls” and additional tasks to be performed at your house under “Home”. If this sounds simple and obvious, good for you. It took me twenty-seven years and reading an entire book (Getting Things Done) to figure this out.

*  *  *

Okay, let’s talk about specific things in your house you might deal with them.


Because this whole bonanza began in my wardrobe, let’s start with clothes. Unlike paper products (which we’ll get to), I don’t have a lot to say about this. If you haven’t worn it in a year, you should really, really consider tossing it. The hardest part for me was figuring out what to do with the approximately fifty-thousand t-shirts I owned. Most of the t-shirts I have (or had), I have for the memories: the vacation I took to Montana, the race I ran in high school. Or, they are gifts to me, amazing gifts, like when Andrew Griswold gave me a navy blue t-shirt that said only “Louis Lamour is the American West”. When we were twenty-one, Andrew and I drove 18 hours straight from Austin, Texas to Albuquerque, New Mexico (with a brief, early-morning detour to Billy the Kid’s grave). We read Lamour’s Silver Canyon to keep each other awake.

I can’t tell you how much joy the t-shirt gave me, and still gives me, because you know what? I kept it. If you love it, if it still has use, keep it. There are other t-shirts, many other t-shirts, that I donated or threw away. For some of them, I took the pictures before they went away.

Now, some of you are reading this and regard taking a picture of a t-shirt as a rather nutty thing to do. Frankly, I can’t believe you’re still reading this essay. I would’ve figured you would’ve stopped a long time ago. For most of you still reading, you are probably nodding your head when you hear me explain that I took a picture of a t-shirt for throwing it away. Most of you will understand, again, just how deeply emotional this process is.

Will I ever go back and look at my t-shirt collection pictures? Probably not. But taking the photographs helped me part with the t-shirts in two ways.

  1. It provided the reassurance that if I wanted to see the t-shirt and remember the time I bought that t-shirt in Austin Texas, back when I had a music blog with my best friends, if I want to remember that, I’ve got a picture.
  2. Taking five seconds take a photograph is a small way of honoring a thing.

Think long and hard about donating clothes. Donate only clothes you would buy. As painful as it may be, the t-shirt you spent 2 decades “breaking in” is just ratty. Toss it.

The great thing about getting aggressive with your wardrobe it’s how much space you can reclaim. And, how much nicer it is to dress for work without digging. Your wardrobe contains only the best fitting, best looking options.

We haven’t even talked about the benefits of the Big Edit (other than the psychological benefit that arises from the opportunity to say “moving on”) because I figured the benefits of this project would be self-evident to anyone interested in undertaking the task (or reading this far into this essay). Quickly: the increased efficiency of living in a space where everything has a place and purpose is remarkable. Furthermore, the increased calm from confronting a cleaner visual landscape is real.

Moving on.


For me, the biggest challenge was paper. When I was seventee years old, I began to realize that I was forgetting a lot of my life that was worth remembering. Conversations I had with people I loved, thoughts that appeared novel and delightful, moments heavy with meaning[3]. Entrusted only to my flighty brain and these things–these precious things–were gone.

So, I started collecting paper to help me remember: playbills, ticket stubs, subway maps, receipts, postcards, letters, notes, notebooks, printed e-mails.

My file cabinets—I had 3 of them: two at home and one at the office—were just filled with nostalgia and memories. I had files for things to do in Louisville, files for places I wanted to camp, files for home ideas, poem ideas. Hell, do I need to say more than, “I’m an English major and a lawyer”? I had drafts of old essays, multiple copies of finished essays. An entire file cabinet was full of all of my legal research: foreclosure defense, consumer protection, insurance bad faith, legal negligence, standards for summary judgment, for motions to dismiss. Articles about poor peoples’ right to counsel, about residential mortgage-backed securities, about predatory lending.

I love to write and my friends love to write. I probably have, (or had) four feet of letters from them.

I am not kidding.

There was no way I was just going to throw this all away.

Like taking a photograph of old t-shirts, I needed a way to preserve the paper before I could part with the paper. I needed a scanner. If nothing else, the scanner would allow need to engage in the fiction that one day I will return and revisit these documents, these memories.

Here’s my advice: if you’re going to scan more than two sheets of paper (ever), buy a Fujitsu scanner.

Look, we could do this the easy way or the hard way. I could spend the next 18 paragraphs telling you technical details of the Fujitsu line of scanners, particularly the ScanSnap 1500M[4]; or you could just say to yourself, “Gee, Ben seems like a huge nerd and really, really, (unhealthfully) into this stuff, so I guess he knows what he’s talking about” and go buy one.


From eleven feet of paper to this...

The ScanSnap 1500 scans up to fifty pages at a time from the top-loading tray and scans them quickly. It scans both sides. It knows when the back side is blank and doesn’t scan it. The scanner performs optical character recognition. While scanning. It comes with Adobe Acrobat 9. Best of all, the built-in software is bombproof and allows you to automatically save scans to a specific folder and integrates stunningly well with Evernote.

What’s that? “What’s Evernote?” you ask?

Welcome to your future.

Evernote is a service that allows you to throw almost anything you want into the cloud. [5] But, unlike Dropbox or other cloud-based file storage systems, Evernote has obviously done a lot of thinking about how users want to capture information and, perhaps more importantly, how users want to retrieve information.

Because the benefits of Evernote are not immediately obvious, I want to spend a couple of paragraphs talking about a few things Evernote does. Your eyes will grow wider and your jaw will drop a little further as you reflect on the potential uses for this application ($45/year for the premium version) in your life.

For my lawyer friends out there: consider your legal research. How many times have you said something like this to yourself, a partner, or an associate: “ I know there’s a case on this. A kid got hit by a bicycle. The judge dismissed the case for lack of prosecution even though it appeared the defense was dragging its feet on discovery.”

So, you go to Westlaw, and, like an animal, you type in some Boolean bullshit like:

bicycle /p dismiss! /5 “lack of prosecution”


If you had that case in Evernote (because you scanned it into Evernote effortlessly with your Fujitsu or because you printed a .pdf while you were researching your prior case and saved it to Evernote), here’s what would have happened: When you uploaded that .pdf or .doc into Evernote, the service would automatically (with a premium version) OCR[6] the document. Then, any search you run in Evernote will include the OCRed text of each document. So, if you remember roughly what the case is about, or what attorney was involved, or a bit of language from the case—basically anything, if you remember basically anything about the case—a search of the OCRed text will allow you to narrow your search of your documents down to just a few possibilities.

And, what’s more, Evernote allows you to tag each note with keywords so that your future self can even more easily find the case your past self was smart enough and kind enough to save and catalog. In the example above, this case would be tagged with keywords like “motion to dismiss”, “ lack of prosecution”, [Name of Client], “discovery”.

So, let’s just pretend your boss just ask you to write a response to a motion to dismiss. Sure, you probably want to try and find a previous response to a motion to dismiss that you can plagiarize for some of the applicable standards. But, you are also going to want to consult the cases in you’re Evernote that you have wisely tagged with a “motion to dismiss” tag.

So, data retrieval is awesome in Evernote. But, getting data and Evernote is just as awesome. I’ve already discussed (and will not belabor the point) that using Evernote and a Fujitsu ScanSnap together is basically the closest thing to magic I’ve outside of my dog’s frisbee-catching skills and the civil discovery process (in which powerful defendants give me information I need to help me prove my case against them).

Evernote has a web application, a PC application, a Mac application, and versions for your iOS (iPhone and iPad) or Android mobile device. Your data is never not with you and you always have a way to capture and upload new things. The mobile applications work with your device’s camera, so inside the Evernote application, you can take a picture, tag it, and save it to your Evernote. Think: receipts on a business trip, business cards, menus. Oh, and when you upload a picture to Evernote, the program will read the text in the photograph and will return that photograph in search results asking for text contained in the photograph.


Evernote is not just for scanned content or photographs. Perhaps the easiest way to use Evernote is as a place to preserve and organize web content. Just press a little button the friendly Evernote folks have made for your browser and—boom—new note. I use this for recipes, incredible blog posts, research, or sites that I’ll want to remember in five years. You could use it, along with a tag like “read later” as for a read later list (though for a “read later” list I personally prefer and recommend Instapaper by Marco Arment.

So, I use my scanner and Evernote for things that I want to catalog, tag, and have access to wherever I am. But most of the things that I encountered during my Big Edit were letters and memorabilia that I just wanted to scan and preserve. Those things did not go into Evernote. Instead, I just created a folder on my hard drive called “File Folder” and created subfolders for the different times in my life. Then, as I was sorting through all of my crap, the papers just went in stacks of varying sizes: middle school, high school, Davidson (subfolders for each year and for time abroad), etc. Then, when it came time to scan each of the stacks, I basically just created one big file (or a few big files) under each folder.


Maybe here’s a good place to talk briefly about the importance of not going overboard with your personal taxonomy. You are not Carl Linnaeus. Try to anticipate how often you’ll need the information that you’re scanning or saving and make the detail of your classification system directly proportional to the frequency with which you will be accessing the documents. I don’t expect to travel down Memory Lane but once every 5 or 10 years, so one or two big files that capture my freshman year in college—untagged, unclassified, unindexed—is just fine. Remember, your mantra during your Big Edit should be: “moving on.” Getting bogged down in developing and maintaining a detailed taxonomy of your crap is a great way to never move on.

Return to Sender

As I was sorting through all of my stuff, I came across a number of letters and notes that I just couldn’t bear to toss. Long, touching letters from people who were or remain dear to me. Short, hilarious notes left on my dorm room door.

Instead of tossing them (and instead of keeping them), I instituted what I called (to myself) the “Return to Sender” program. It is exactly what it sounds like. Last week, I shipped off probably a foot of old letters to past loves, good friends, best friends, and family.

There will probably always be things that I leave unsaid that should instead be said. (There are a lot of things I leave unsaid because even I know they should be left unsaid.) But, in the letters I wrote to accompany the returned letters, I said a lot of things that had needed saying for a while.

Look, if you’re this far into this essay, you probably are already invested into some of the outcomes that flow from The Big Edit: cleaner house, less hassle trying to find stuff, a kind of calm that arises from this ritual purge. But, add to this the opportunity to renew your gratitude for the people in your life and gain new perspective and even closure on old, perhaps painful, relationships. Combining a Big Edit with a Return to Sender Project became an unexpectedly powerful process of…what? Purification? Healing? Understanding? Thanksgiving?

All of that.

*  *  *

Okay, so that’s paper. What about all the other stuff in the house? Again, if you want a longer exposition on each room, please read It’s All Too Much by Peter Walsh. It’s great. I just want to run through a few of the things that worked for me when dealing with kitchen utensils, memorabilia, photos, books, movies, and LPs.

Kitchen utensils

Take all the kitchen utensils in your drawer(s). Dump them into a box. Put the box in the corner of the kitchen and as you need something, put it back in the drawer(s). At the end of the month, take the utensils that are still in the box somewhere else (the basement, the trash, the Goodwill). I enjoy cooking so much more now that I’m not digging around eighteen different useless implements to find the spatula.

Memorabilia (and by this I mean tangible objects that hold a memory, not “baseball cards”)

Like hilarious t-shirts, take a picture, throw it out, and move on. Either that, or keep it and display it in a way that honors the thing and the memory, as Peter Walsh would say.

Memorabilia is hard because we feel like if we toss the thing, were tossing the memory and potentially disrespecting the subject of the memory (often grandparents). I find taking a photograph helps by reassuring me that’s some record of the thing has been preserved.

Photos (and an aside about computer backups)

I use to make a digital copy of every single one of my hardcopy photographs. When returns my photos to me, I’m not throwing them away. I’m not crazy; I’m storing them. Photos are too important to leave only in digital format.

While were talking about photographs and preserving them, I want to talk about developing a vigilant backup system for your computer files. Observant readers will have already noticed that many of the solutions to problems I encountered during my Big Edit involve digitizing memories. It has always been reckless to not have a backup system in place, but in 2012 the backup solutions are so convenient and so accessible to even non-nerds that a failure to backup your data has migrated fro reckless and is now simply inexcusable.

If you are a Mac user, take advantage of the Time Machine functionality in your operating system. I combine Time Machine with a Time Capsule router for automatic wireless backups.

Because one backup is not enough (especially if that backup is also going to be at your house), consider using a program called SuperDuper to create an exact copy of your hard drive on an external disk. Store that external disk at your office or some other off-site location. Every six weeks to two months, use SuperDuper to wipe the external disk and create a new backup of your hard drive.

Regardless of what operating system you use, explore online backup solutions. There are many available. At present I don’t use one, but hear good things about both Mozy and Crash Plan. Online storage has the twin benefits of being convenient and off-site. Whatever backup system you use should include your data going to a place that is not your home. (When thieves break in, they take everything. When fire breaks in, it burns everything.)

There is an entire Mac Power Users episode about backup and I highly encourage you to listen to that episode before making any decisions about what backup system is right for you.

Seriously, this is too important not to get right. Don’t be an ass: back up your data.

Media: Books, Movies, and LPs


Books are brutal. Asking me to throw away the book, or donate a book, or sell a book, is like asking me to give away a portion of my brain. Or, a potential portion of my brain in the case of a book I haven’t yet read. I support organ donation. Someday. Not yet.

In college, my favorite day of the semester was the day I went to the bookstore and got all of the books for my classes. I was an English major and even for an English major I took far too many English classes. I bought a lot of books. I enjoyed Book Buying Day so much because the books were so heavy. And, as I carried them across Davidson’s small campus I would look down at the box and think, “In just three months all these books will be in my head and weigh nothing. What’s more, they will be bouncing and jostling around with all of the other books that live up there.”

Books remind me who I was, who I am, and who I want to be. Sitting at my desk in the living room, I can look across the room at my bookshelf and remember that I am a person who loves the outdoors, loves Kentucky, cares deeply about politics, and who shambles toward some semblance of a spiritual life.

Confronting my bookshelf is confronting myself and the reality that I have increasingly less time in my life to read. I have to confront the fact that all those books I aspire to read again will likely go unread. And so many books that I hope to read for the first time will similarly remain unread. This is a minor tragedy to me. But it’s reality.

Now, this doesn’t mean that I tossed all my books—not even close—I still kept a lot of books that I hope to one day read, either for the first time or again. I kept a lot of books that I expect I will give away to someone who says the magic words to me some night at a party. And I kept all of my grandmother’s books. I’m not crazy.

But, what I did do was be real with myself about the time I have available for reading. Five boxes of my precious books are now sitting at my church awaiting our yard sale. By June, there will likely be two or three more. It was hard.

Moving on.


I don’t have a ton of DVDs, so I am not concerned about reducing them to files on my hard drive. But, I do have a friend who has ripped all of his DVDs onto a hard drive and connected that hard drive to his PlayStation. Now, he has immediate access to all of his movies from his Playstation controller. He loves it and it appears to work well for him.


(For people without LPs, please skip to the next section. These are not the droids you are looking for.)

My record collection was perhaps the most obvious disconnect in my house between the reality of my life and the reality of things I owned. Gathered at yard sales over many weekends in my 20s, I’ve got a pretty good collection of some of my favorite music.

Favorite music that I never listen to.

The reality is, I listen to nerdy podcasts, not music. So, I decided to sell my LPs or at least donate them to my church’s yard sale. Before I did that though, I again relied on technology to help me digitize some of my favorite albums.

I used a program called SoundSaver, an application that works on either Mac or Windows machines, and used the Alesis MultiMix 8 USB soundboard [7] to interface between my record player and my MacBook Air. And, I listened to the records as this rig recorded them on my Tivoli Model One. They sounded great through this little guy. 

SoundSaver is a pretty good application. It advertises itself as capable of detecting tract breaks and automatically finding album information like track names. In the best case scenario, the automatic track detection will get you close. You will still need to go into the waveform and manually set each track break. Let me put it this way, you’ll have the opportunity to listen to a lot of the beginnings and ends of songs you own as you place the breaks yourself or ensure that the automatically placed breaks are accurate.

When you’re using automatic track recognition, tell the program the exact number of tracks on the album (don’t use auto), set the “seconds of silence” to “4” and the silence threshold at 1%. These settings gave me the best results, but even on the settings each track will start about half a second after the song actually starts. Which is annoying.

The good news is, once you set the tracks, you can tell SoundSaver the name of the artist and the name of the album and it will automatically (usually) name each of the tracks for you. This saves a lot of typing.

All in all, I’m happy with the app, though more accurate track recognition and the ability to scroll horizontally across the waveform with Apple’s Magic Mouse or Magic Trackpad gestures would be amazing.

After having wrestled with SoundSaver for hours (weekends), please don’t tell me if there is a better product on the market.

I initially started out digitizing my LPs with the goal of getting rid of all my records and my record player. Fortunately (or unfortunately), I had so much fun in the process of listening to and editing many of my favorite albums, I have abandoned my plan of going entirely digital. Instead, I plan on keeping the record player and ten or fifteen of my favorite albums and adding a few to my pared-down collection each year. People who pine for vinyl will understand how this could happen.

*  *  *

So, I think that’s about it. This was my Big Edit during which I battled dragons, rocked out, got dirty, and got grateful. It was a hell of a good time.

Moving on…

  1. All identifying me as me, except for the Elvis driver’s license I picked up at Graceland in 1996 and used as a joke with bouncers for years. They found it hilarious. Always. Bouncers: unanimously affectionate for Elvis and tolerant of the shenanigans of the underaged.  ↩

  2. It’s as though this poem was hand-crafted to be read aloud by Garrison Keillor  ↩

  3. For those who remember being seventeen, you’ll remember there are a lot of moments heavy with meaning.  ↩

  4. I got the S1500M, which is the Mac-specific variety of this scanner. For PC users, you’ll want to rock the standard ScanSnap 1500.  ↩

  5. Big ups to fellow attorney Tad Thomas for turning me onto the usefulness of Evernote as a research repository.  ↩

  6. OCR is “optical character recognition” for the non-nerds. The scanner “reads” the words and figures out what they are.  ↩

  7. Props to Stephen Kertis for recommending this soundboard. For $230, it does everything I need it to do–from recording LPs to recording podcasts.  ↩

My Internet Friends and their Podcasts

by Ben Carter

Last night, I asked a buddy of mine at the Legal Aid Society’s Brush, Bottle, and Barrel event1, “What podcasts are you listening to?” At this point2, Erin discovered she urgently needed to go get a drink.

So, I told my friend I’d send him some recommendations. I accidentally turned it into a blogpost:

Dear […],


Now, onto a more pressing matter: podcasts.

Like I said last night, I listen to many of the podcasts offered on the mighty 5by5 network. Dan Benjamin, the shows’ co-host has invested his time and money into building audio tools and the web infrastructure to create great-sounding podcasts from Skype calls with his co-hosts located in Philly (John Gruber), San Francisco (Merlin Mann), Boston (John Siracusa), Somewhere Outside of New York that’s not Brooklyn (Marco Arment), and Canada (Jim Dalrymple). The website is All of the stuff the guys talk about on that week’s show are captured in hyperlinks on the site.

I discovered 5by5 because Merlin Mann started podcasting there with Dan on a show called Back to Work last year. It wasn’t long, though, before I branched out and found these other great shows. Dan appears on all of them and I find myself sort of continually amazed by what a good radio personality he is. He does a great job and all the shows are deeply entertaining in no small part because of Dan’s ability to draw out the best of his co-hosts’ personalities. Here’s a brief summary of the shows so you can know where to start:

Back to Work: Dan and Merlin will spend the first 15 minutes starting the show and talking about children and what Merlin ate that day. Then, they will discuss some aspect of how to know whether you’re spending your time and energy on the right shit. Like I said, I started listening to 5by5 for this show. Merlin Mann is basically my favorite web personality (more on his other stuff in a bit).

The Talk Show: John Gruber writes Daring Fireball, which is one of the best Apple sites out there. This is going to be your general-purpose Apple news show. John’s personality and perspective on things is great. You’ll see what I mean. They will occasionally talk baseball or football. Last year, they watched all the Bond flicks and talked about them at the end of each show. By the time I discovered 5by5, John and Dan had already recorded like thirty previous episodes. Even though the news was old, I still went back and listened to them, just because Dan and John are so fun to listen to.

Hypercritical: John Siracusa is known for his exhaustive reviews of new iterations of Mac OSX at ArsTechnica. He is not satisfied with anything. Erin calls him “that complainer guy”. His targets range from TiVO, to video game controllers, to toasters. This podcast can get fairly technical when Dan and John start talking programming languages, memory management, etc. But, I still find a glimpse into the computer programmer’s world sort of jaw-droppingly interesting.

Build and Analyze: Marco Arment was one of the two co-founders of Tumblr. He quit and started Instapaper. He’s like 28. This is a show ostensibly for iOS developers and you get a sense of what it’s like to build an app for the iPhone, the decisions that go into making it and maintaining it, and dealing with Apple’s decisions that affect independent software developers. Also discussed: coffee, running a small business, and minivans.

The Ihnatko Almanac: Chicago Sun-Times’ technology writer, Andy Ihnatko, spends thirty tight minutes3 with Dan each week. Interesting dude. Earnest.

Amplified: This is 5by5’s newest show. Jim Dalrymple ( and Dan talk Apple and guitars. Jim has the best laugh of any human I’ve ever heard. Not for people sensitive to Canada jokes.

There are a couple of other 5by5 shows I listen to that are no co-hosted by Dan Benjamin. (By the way, all of these people are great to follow on Twitter, if you are a Twitterer. Their handles are all available on Additionally, there is a separate show, After Dark, which is exclusively Dan and his co-hosts after the show is over. Good times.)

Geek Friday: Faith is as charming as Jason is creepy. It’s a great combo.

Mac Power Users: In terms of practical advice on getting the most out of your Mac, this is the podcast that you must listen to. David Sparks and Katie Floyd are both attorneys by day and spend 90 minutes or so walking you through one particular application or process each week. They also have smart people on in their “Workflows” episodes to explain (specifically) how they use their Macs (or iOS devices) to get shit done.

If all of this is not enough for you, there’s The Critical Path with Asymco writer, Horace Dedieu. This is the podcast I listen to when I run out of everything else, not because it’s not good but because it’s just drinking from the firehose with Horace: Dan rarely interrupts Horace, so it’s just one long, intense stream of analysis of Apple’s performance as a company from an intense dude. But, Horace is great to listen to for an understanding of what drives Apple’s current dominance. He is a student of Clay Christensen who pioneered the idea of disruptive theory in businesses and Horace applies it persuasively to Apple and the tech sector.

5by5 is so good, even the couple of ad spots Dan does during each show are useful. I use a number of the services that advertise with 5by5 exclusively because I discovered them on 5by5, including Squarespace, Smile Software’s Text Expander and PDFpen Pro, Agile Bit’s One Password, Harvest (time-tracking), Wufoo (online form-builder), and Mail Chimp.

There are two other podcasts I think you should check out, both involving my Internet Friend, Merlin Mann:

Roderick on the Line: Merlin calls John Roderick who is the lead singer of The Long Winters each week. John has walked from Amsterdam to Istanbul and is just one of the most interesting people I’ve ever encountered. This podcast is really kind of an archeology of both Merlin and John’s minds and pasts.

You Look Nice Today: Three funny guys being funny together. Now you are starting to get a sense of why Erin walks away when I start talking about podcasts…

Until about two weeks ago, I used the built-in music player on my iPhone to listen to podcasts. Since then, I've been using an app, Downcast, to download and stream my podcasts. There are other "pod catchers" out there (like Instacast), but I think Downcast is the best. Incidentally, 5by5 is lauching an app that will allow you to listen live to any of the shows currently being recorded. Look for that in the next week or so in the iTunes app store. 

Good seeing you last night. Hope these podcasts help keep you entertained as you traverse our great Commonwealth. Keep up the good work.


UPDATE: Also, I podcast my awesome minister's sermons each week. If you're interested in hearing about social justice for the 21st Century, subscribe on iTunes. Here's Douglass Boulevard Christian Church's website

  1. What? You didn’t go? Shame on you. Well, you can still donate to Louisville’s Legal Aid Society. ↩

  2. (and at every point at which I mention podcasting) ↩

  3. As opposed to Siracusa and Merlin Mann’s willingness to go ninety minutes each week. (Not complaining.) ↩