Knowledge leads to application

I had a philosophy professor in college who would conclude long lessons on the world’s great thinkers by asking us how we’d turn his or her ideas into concrete, observable action. Something to physically do. It was a tough exercise but ultimately rewarding.

Today I see many ideas that generate incredible pieces of technology, but few answers to the question, “But what can I DO with this thing?” Friends and family often come to me with their iPad, smartphone, etc. and say, “How can I…” or “Will this thing…” and so on. Fortunately, I love answering those questions. I also suspect that other people have them.

Within the next few weeks, 52 Tiger will answer that question, long-form, on a regular basis. Expect real things you can actually do to improve your day at home and at work. Simple projects — both large and small — that use technology to enhance life at its most significant moments. Like playing with your kids while they’re young and think you are The Most Awesome Person In The World, traveling for work with ease or doing The Thing You’ve Always Wanted To Do.

Technology is supposed to “make our lives easier.” Don’t let the God-forsaken fax machine at work let you believe that was a false promise. Your gadgets are tools, and you are the artful craftsperson. As someone who’s worked in the technology industry for 14 years, first as an IT Director and now as the Managing Editor for one of the Web’s leading tech sites, I can show you how.

Stay tuned.

My Scrivener workflow problem

I love Scrivener. It’s my go-to software for large writing projects. Scrivener makes organization easy, from chapters to research. However, I can’t figure out how to use it when tracking changes with an editor.

I’m currently collaborating on a book on Lion. As I complete each chapter, I export it to Word, enable Track Changes and then turn it in for copy editing, technical review, etc. It comes back with notes, I make revisions, re-submit and so on.

At that point, I never touch Scrivener again, because it can’t (at least as far as I can see) track changes the way Word can. That’s unfortunate on one hand, because it’s a super piece of software, and a real nuisance on the other, as my careful organization is lost when the project becomes a single Word file.

If you know how to work with Scrivener while tracking changes with an editor or other party, please let me know. I’d love to figure this out.

Heather Armstrong in the New York Times Magazine

Congratulations to Heather on this mostly fantastic piece in the New York Times Magazine. Why “mostly?” Gruber nails it:

“I’ll tell you what I don’t like about it. The title: ‘Queen of the Mommy Bloggers.’ I think ‘mommy blogger’ is a term intended to be dismissive.”

I totally agree. She’s not a “writer,” she’s a “mommy blogger.” That probably means she writes about pee pee and poo poo all day, right? Oh, look at this quote from NYT Mag writer Lisa Belkin:

“By talking about poop and spit up. And stomach viruses and washing-machine repairs. And home design, and high-strung dogs, and reality television, and sewer-line disasters, and chiropractor visits. And countless other banalities of one mother’s eclectic life that, for some reason, hundreds of thousands of strangers tune in, regularly, to read.”

It’s how she talks about those things that makes her phenomenally successful. Her stories are instantly relatable, entertaining, engaging and very well-written. Incredibly well. Some of the best writing advice I ever received was: “Nobody cares about you. They care about themselves. Write so that they see themselves, their experience, their world in your words.”

Heather does this with seemingly effortless grace, and that’s why millions of people know who “Dooce” is. As John points out, that “some reason” is that she’s a great fucking writer.

My book: Using Your iPad as a Business Productivity Tool

At long last, I can finally announce that my book, Using Your iPad as a Business Productivity Tool, is available.

Writing this book has been an incredible challenge and the realization of a dream. I’m extremely proud of it, and feel certain that you’ll enjoy it, too. Aimed at small business owners and independent professionals interested using the iPad as a business tool, Using Your iPad as a Business Productivity Tool describes how to incorporate the iPad into your workflow and your business successfully.

The book will be available on the iPad iBookstore for two weeks of exclusivity starting on February 28th. After that, it will be availabe for the Nook, Kindle and Sony Reader. In fact, Kindle pre-orders begin today.

It’s a tremendous honor to write for you, and your purchase helps me to continue to do so. I appreciate your time, attention and purchase tremendously. For more information, look here.

And thank you. Sincerely.

The shitty first draft

I can’t remember where I first heard the phrase, but it’s important to give yourself permission to write a shitty first draft. Shawn Blanc’s recent exploration of his writing habits reminded me (and Randy) that your first draft of a piece will be terrible. That’s fine. Record your main idea or point thoroughly on that first pass. Make it pretty later.

The same can be said for your writing in general. I’m still very much a student, but I’m worlds better than I was a few years ago. Just keep at it.

Update: Several of you have written to point out that the concept of the shitty first draft comes from Bird by Bird by Anne Lamott. Thanks.

MacBook Air as the perfect writing machine

John Brownlee has written a post that’s so eerily similar to my own experience that it’s almost supernatural:

“The MacBook Air might be the gadget that I’ve spent my whole life waiting for. It’s a device that with silent elegance addresses every demand…that I could ever make upon a tool meant to allow me to pursue a lifelong passion.”

Agreed. Here’s where it gets eerie:

“But in the MacBook Air’s perfection as a writer’s machine, it…robs me of the crutch of imperfect tools to explain my own mediocrity. The MacBook Air might be the perfect laptop for a writer, but that doesn’t change the fact that I’m not nearly as suited to the task of writing as it is.”


“I only became one professionally by accident, and I only became successful at it because otherwise I would have starved. I still don’t write fiction. The MacBook Air might be the perfect device, but it makes me despair that I will always come up short.”

I became a writer quite by accident, too, having answered a call for bloggers at Parenting Magazine long ago on a lark. When my day job disappeared years later, my only option was to get very serious about it, and today I’m a news editor at TUAW. Still, I’m Caolo, not Gruber. The MacBook Air is a reminder of that fact.

Sure, I could buy a Highland Green 1968 Ford Mustang GT 390, but that won’t make me Steve McQueen.

[Via ForkBombr]

Blogging with Scrivener, TextMate and Markdown [Updated]

Here’s a great post from Chase Reeves, in which he describes how he blogs with Scrivener, TextMate and Markdown. I’ve been using Scrivener for a while now, but only recently added TextMate and Markdown. I’m going to adopt Chase’s workflow with one alteration.

Instead of copying the HTML from TextMate and pasting it into a browser-based compose window (he uses Posterous in his screencast), I’ll copy my Markdown post from Scrivener, open a Markdown blog post template in TextMate (via the Blogging Bundle) and then publish with Control-Command-P.

In fact, I’ll see if I can create an Automator workflow to further automate the process, even though it’s pretty quick as it is. In the meantime, check out Chase’s post.


I’ve gotten several comments and questions about this setup, which I’ll address here. First of all, I’ve learned the hard way that composing blog posts in a browser is a bad idea. Unexpected crashes, network outages, etc. can destroy your hard work. So I’m after alternative desktop software.

Many of you suggested MarsEdit. I’ve tired to get into it several times without success, but I couldn’t tell you why. After much prompting from Brett, I downloaded TextMate, mostly to take advantage of his Blogsmith Bundle for TUAW blogging. It’s so obscenely useful that I couldn’t imagine working without it at this point. Bundles add a tremendous amount of functionality to TextMate, and Brett’s work is a prime example of that. It’s a huge time-saver.

Meanwhile, I’ve been working on a large writing project since November with the help of Scrivener. While TextMate is the race horse, Scrivener is the meticulous jockey who ensures that everything is in order before hitting the track. I’ve begun using it for organizing long posts on TUAW and 52 Tiger. I can’t publish directly from Scrivener, but that’s OK, as publication isn’t its  job.

TextMate might seem like overkill for blogging, but I’ll argue that’s not the case. The time-saving benefits of bundles can’t be overstated. For my personal blogging, I use Brad Choate’s Blogging Bundle 1 and this Markdown plugin for WordPress. 2 Once a post is pasted into TextMate, I can do so much more with it than simply publish, including saving local copies, drag-and-drop image upload, etc.

Lastly, don’t forget that I’ve set up Scrivener to sync with PlainText for the iPad for cloud-based, on-the-go editing of works in progress.

I’ll admit that I am bothered by the copy-and-paste step, but it’s hardly a deal-breaker. If you have any other questions or comments about this workflow, please let me know.

  1. Here’s an overview screencast.
  2. Incidentally, if you like writing in WordPress’ compose field but still want to use Markdown, check out Brett’s WordPress plugin for doing just that.

Tune out and benefit

Iain Broome has discusses how eschewing technology for a week benefited his own writing:

“I’ve found it really tough to concentrate on [new ideas] while allowing myself to be bombarded by constant messages and constant flow of information that I get by being a writer who operates online.”

I completely agree, and had a similar experience while in Maine last December with no Internet access, music or television. By the time I got home, I had pages of new ideas written down.

As a writer who finds much of his source material online, I’m constantly reading, evaluating what I’ve read and, on some occasions, responding to it. This internal processing leaves little room for the kind of creative thought that Iain discovered in France.

In fact, I’m convinced that Twitter is making me dumber.

Of course, you needn’t go away on vacation to reap the rewards, as Iain explains. A weekend or even a day spent unplugged and in a quiet setting can be beneficial. Try it out and enjoy.