How Lawyers Work: Kyle E. Mitchell, Journeyman Deal Mechanic & Overfed Bookworm

In this week’s edition of How Lawyers Work, we hear from Kyle E. Mitchell. Kyle grew up in the Piney Woods of Texas, beating on drums and fiddling with computers. He studied at UT Austin for way too long, then went west to California to practice law. These days, he advises companies big and small on all manner of intellectual property, commercial, privacy, and security projects related to software, especially open source.

You can follow Kyle on Twitter.

What apps or tools are essential to your daily workflow?

I’m a technology person—and a programmer—and I have been since I was a little boy. Zero apps are essential to my daily workflow, and God forbid—I avoid specialized, glitzy apps in favor of robust, versatile tools whenever I can. I use tools like plain text files, backup and file sharing services, tiny macro-esque computer programs, e-mail mailboxes, that kind of thing. Essentially, I use the sticky notes, index cards, and filing cabinets of the computer world. Plus a few tools of my own design.

There’s a great old cooking show, Serious Eats, with Alton Brown, back before he turned heel. Alton called single-purpose kitchen gadgets “unitaskers”. He railed against them. They cost a lot of money, pile up in the kitchen, eat up space, and usually don’t work very well. They don’t play nice with other tools or techniques. You don’t grow as a cook by relying on them.

There are so many unitaskers in legal technology. Apps for tracking time. Apps for tracking contacts. Apps for project management. Note taking apps. Billing apps. Tenths-of-an-hour watches. Bates stampers. Legal-size paper. That legal keyboard that just came out. Unitaskers glommed together in unwieldy combinations, as “platforms”, like those 30-plus-item, three-quarter-pound Swiss Army knives you sometimes see in novelty stores, and never see in pockets.

I try a few, now and then. None are ever a perfect fit for how I want to work, or how clients want to work with me. None is ever flexible enough to stay with me as I get wiser and change my mind, setting me up for a jarring transition. Rarely do more than two work together reliably, or at all, for any length of time. Rarely are they even worthwhile, on their own merits, after the new-gizmo shine rubs off. Something general and standardized usually nets out better. Letter paper is better than legal paper, even for law.

They can be worth it if you do one thing, exactly the same way, all the time. My kitchen has a rice cooker, my motorcycle garage a battery charger. In the office, it’s a Fujitsu iX500 sheet-fed scanner. I take a lot of handwritten notes, and I scan all my mail, too. Sometimes hundreds of pages at a time. The scanner does it fast. Someday, I’m sure it will stop playing nice with my router, my phone, my computer, something. But it’s worth the high price for time saved until then.

I do time entries, contacts, task tracking, billing, accounting, record keeping, notes, and as much writing as possible in plain text files. The kind of thing you’d make in Notepad on Windows, or with WordPad on a Mac. They’re easy to put in folders, share, back up, cross-reference, encrypt, and search. It’s easy to copy and paste their text to and from every other program, on any computer, phone, or tablet. They take almost no hard drive space.

My background comes through in the little programs I write to work with those files. To pull out all billing entries for a particular client. To spit out today’s to-do list. To pull down all the files I need for a client project. And so on. The kinds of programs students write in Programming 101.

Those “beginner” projects seem like toys or make-work until you realize text files are the best organizing principle we’ve ever come up with for doing office work with computers. The most famous computer demo of all time, the “Mother of All Demos”, showed it all off way back in 1968. Then it was a key idea behind UNIX, an operating system started a year later, that lives on in Linux today. Your computer and phone may not run Linux, but nearly all the online services you use—from Google to Dropbox, Facebook to EDGAR—almost certainly do.

Both plain text and simple, versatile tools were part of the UNIX philosophy. I understand we used to have software along those lines in office technology, before my time. Some very famous writers, and more than a few prestigious courts, still hold on to “ancient” word processing software from that crude era, before they took on oodles of pointless features, like ships gaining barnacles. I wasn’t around, but in a way, I’ve gone back to it. I don’t roll my eyes so much about WordPerfect at supreme courts anymore. It doesn’t surprise me to see dozens of popular, “distraction-free” writing apps for sale, essentially reprising Notepad or WordStar for each new gadget.

Of course, I can’t ever entirely escape Microsoft Word, since others use and expect it. But it’s the classic example of an app gone wrong. So many features. Frankly, I’ve written software for Word, and I’m still never entirely sure what automatic numbering will do next. It’s like a touch-screen washing machine with WiFi. Educated consumers get lost in all their options. Skilled technicians can’t reliably diagnose or fix them. Teenage ne’er-do-wells from far-flung jurisdictions indiscriminately hijack them, to mine Bitcoin and launch denial-of-service attacks.

My goal for tools like Word, and to a lesser extent Adobe Acrobat, is minimization. My strategy is quarantine. I rent a Windows computer in a data center outside LA. That machine has Word, Acrobat, Google Drive, and Dropbox. I can dial into it from any other computer when I need to be sure I’m using exactly the same unreliable program that opposing has. But that’s less than 10% of my time, even in multi-turn negotiations. Client communication, research, preparation—I can do all the rest my way. When I’m driving the process, say for an entity formation or a sales playbook, I can do it all my way.

That mostly means looking at a web browser and a terminal emulator, the black screen with fixed-width text and a blinking cursor where you may remember typing WIN in the 1990s. The web has all the raw material. There are literally decades worth of free tools for terminal emulators, dedicated exclusively to working with text. Programs to search. Programs to sort. Programs to edit, print, e-mail, translate, and spell check. Programs to share, copy, back up, and so on. They all take text in, and spit text out, so they’re easy to use together. Today’s to-dos for client X? That’s a search for X in my to-do files, followed by a sort, then some formatting. I type todos Acme and I see it.

I’m always swapping tools and services in and out, to try new things. But to give a sense, a few standouts at the moment:

  • FastMail for e-mail and calendars. Very reasonably priced, reliable, and compatible. The web interface is far and away better than Gmail, and the service works well with phones and other mail programs, too.
  • Rclone for sending files to and from various file-sharing services, like Dropbox, Box, Google Drive, and Amazon S3. I have clients that use each one, sometimes more than one.
  • Vim for editing text files. A popular old-school option among programmers.
  • Feedbin for reading RSS feeds from blogs and news sites.
  • Pinboard for saving and organizing bookmarks across computers.
  • Reeder and Pushpin on iPhone let me riffle through my RSS feeds with my thumb, like an email inbox, crossing off or bookmarking posts to Pinboard for reading later.
  • Git, a tool for tracking changes to folders of plain-text files over time, and sharing changes across computers. Standard in software development. Many of my tech-sector clients prefer to use Git for legal documents, too.
  • Unoconv converts files between various Office file formats, such as from .docx to PDF. I can also use this to extract the text of a Word file to plain text.
  • PDF Expert on iPad for PDF reading and annotation. Studio Neat’s Cosmonaut stylus works great for highlighting.
  • sends and receives faxes, which is often the best way to get things into secretaries of state. I have a little program just for sending a PDF to Sacramento.
  • sends postcards, letters, and checks by mail.
  • Cron runs other programs on a schedule. I use it to do everything from backing up files to sending e-mail at specific times and pulling down weather forecasts. The foreman for my own private office-robot army.
  • Vimium, an extension for Chrome and Firefox, lets you navigate webpages and click links with the keyboard.
  • Junior legal notepads, stuck with binder clips to a clipboard sawn down to exact size. I buy in bulk. Don’t be like me, kids. Stay away from fancy pens.

I’ve also built a few tools of my own for composing, assembling, sharing, and analyzing contracts, under an open source project called Common Form. The Common Form tool kit lets me write out contracts and other structured documents, and pieces of them, as plain text, in a way that lets the computer be more help. Imagine a giant index card catalog, with a card for every provision of every contract you’ve ever written, plus an automated word processing department that keeps everything filed, and does all the technical grunt work of checking combinations of those pieces, and spitting out formatted documents for you.

It’s been a boon to my practice. Especially when I get to take a first draft, I don’t worry about numbering, keeping references correct, checking my defined terms, signature pages, or spitting out multiple documents based on a template. I can focus almost 100% on the substance of what I’m trying to cover, the terms I’m trying to express, and using clear, plain language. It’s a much more tiring, concentrated experience—technical edits used to work as built-in brain-breaks for me—but that’s made me a better drafter.

Thanks to some help from Ansel Halliburton, another coder-lawyer here in the Bay Area, we also have a nice suite of automated annotation programs, which work a bit like opinionated spellcheckers. They point out archaisms, wordy phrases, and usage comments from Ken Adams’ A Manual of Style for Contract Drafting as we type. Behind all that, we’ve done a lot of work pulling together long lists of words or phrases that pose problems of various kinds, stylistically and substantively.

There’s no substitute for fresh-eyes reads in contract drafting. But Ansel and I have learned there’s no substitute for automatic checks, either. The mind just isn’t good at certain kinds of rote work, and shouldn’t be. Smart is spending the limited focus you have where it gets the most done for your clients.

On the hardware side, I can’t overemphasize the need for a quality ergonomic setup. I learned the easy way that RSI, carpal tunnel, and back problems are no joke, by watching other people learn the hard way. I was lucky.

I use a Kinesis Advantage keyboard, accompanying numeric keypad, a Logitech Expert Mouse, and a Herman Miller Embody chair. The combo cost about a thousand dollars, with a used chair from an office liquidator. That’s what I could afford at the time, and it was easily worth it. If you have less to play with, try a Microsoft Natural 4000 keyboard. I’ve owned five or six. I recommend it constantly.

I listen to music while working, and splurged on good closed-ear headphones and a USB digital-to-analog converter. When I’m really bearing down on something, I’ll wear a $10 pair of slim-profile pistol shooting earmuffs. Same isolation, or better. And just as comfortable to wear for long periods. Great on airplanes, too.

What does your workspace look like?

I rent a fairly typical professional office in Dunn’s Block, a historic building just south of the perennially “revitalized” part of Old Oakland. Old Oakland was the center of downtown until freeways replaced rail and telegraph as the arteries of the city, and still a hop, skip, and jump from most transit and city hall.

The building’s one of those classic, ground-floor-retail combos with a long, skinny staircase from street level to the second floor, lots of short wooden banisters, and comically high ceilings. (I get the feeling professionals of yore were shorter in statute, and somewhat loftier in ambition.) The main attraction is the sunlight. I have an interior office, but a tall window at the front. Sunlight shines down from the roof through the third floor. I’m not totally cut off from the sun cycle.

The office is almost entirely for me. I grabbed a couple guest chairs from a next-door neighbor moving in, along with used furniture from the local used shop and a salvage yard. But I almost always meet clients at their offices, rather than mine. So it’s more of a designated focus place. A tool for better making believe that practice and life respect any kind of boundaries.

I’m definitely of the messy-desk, clean hard drive school of lawyering. I scan almost every bit of paper that I receive and write, but there are still so many print resources available only on dead-tree. At this point, the books rule pretty much every flat surface and a good chunk of the floor. Their only real competitor is the computer setup and the scanner.

Basically, it’s a disaster. But lots of order from that chaos.

How do you keep track of your calendars and deadlines?

I keep calendars online, with FastMail. CalDAV for sync, especially with the iPhone. Meetings. Phone calls. Conferences. House calls. Continuing legal education. That kind of thing.

All my task management is in a folder full of plain text files, one per client or category. Each item on one line. If there’s a date code, YYYY-MM-DD, that’s a deadline.

I track changes to the whole thing with Git, which means I can travel back in time to any point, and see what I’d marked done, to do, or made changes, and when. The same tool makes it easy to change my lists from any computer.

What is your coffee service setup?

I’ve lost count of how many importers, roasters, distributors, and coffee shops at different degrees of swank I have within walking distance. Blue Bottle’s HQ, Four Barrel’s roasting operation, SLOJOY roasting, Bicycle Coffee’s HQ, Peerless, Caffe 817, Modern. Eat your heart out.

My office has a Russian-style samovar for tea service. I know I’ve got it bad when I hit two pots of concentrated zavarka per day. Usually in winter.

What is one thing that you listen to, read, or watch that everyone should?

Dangerous question. Read people who disagree with you.

What is your favorite local place to network or work solo?

I try never to go anywhere with the express goal of “networking”. Oakland is a vibrant place. Be here and be open, you’ll find people. The Town’s surprises are often way better than anything you might have had in mind.

I work solo, so whenever I work, I work solo. That’s what the office is for, to keep me from holing in too long at home.

What are three things you do without fail every day?

Read. Write. Curse.

Who else would you like to see answer these questions?

Luis Villa

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