Writers I Read: Dave Caolo

For the fourth installment of the “Writers I Read” series I’m sharing my conversation with Dave Caolo, TUAW news editor and curator of 52 Tiger.

Stephen: Dave, thanks for being willing to chat with me a bit. I know that you stay busy editing at TUAW, yet you still find time (and energy) to write 52 Tiger.

From the outside, it seems like your day revolves around words. What are you up to when you’re not behind your keyboard?

Dave: My day starts at 7:00 AM when I quickly review posts prepared for TUAW while I slept and schedule them for AM publication. Then I’m off to get my kids to school. I return to my desk around 8:00 – 8:10.

From there, it’s a lot of writing. My co-workers and I use IRC as a virtual office for coordinating stories and real-time communication. While we’re finding stories and writing them up, I’m also noting things I’d like to discuss on 52 Tiger in Notational Velocity.

My TUAW duties end around 2:00 PM when my kids return from school. After they arrive I’m in Dad Mode until 7:00 PM when they go to bed. That’s when I plop back into my chair and catch up on reading with my iPad and work on posts for 52 Tiger. I usually finish around 10:00 PM.

My biggest challenge since going independent three years ago has been time allocation. In the course of a day, I must be a writer, editor, father, husband and neighbor. At this point I’ve devised a workable routine but it can all change in an instant. A sick child, malfunctioning network, etc. can toss the whole thing out the window. So really, the bulk of my workday is responding to the huge number of little things that pop up unexpectedly.

Stephen: I have to say that I’m impressed by people who can work from home. It is probably because both of my kids are still so young, but if I stay home, I usually end up playing games, watching Thomas the Tank Engine, or something other than working. I’ve gotten better at putting my shields up, but its hard.

You seem like a very busy dude, with a hectic schedule. What tools do you use to keep tasks under control?

Dave: It’s a tightrope walk. I’ve got to be an excellent father, and that includes earning enough money to provide my kids with clothes, a place to live, a decent education and so on. I’ve also got to be available to them, and not always staring at a glowing screen. This is the single most difficult aspect of my work.

It’s easy to assume that independent workers with a home office are free to do what they please whenever the mood strikes. You’re “your own boss,” right? Actually, you’ve got 10 bosses. Or 15. Or however many clients you have. Each one requires and deserves your full effort and attention.

When my kids were home each day it was very hard to get things done. Now that they’re both in school full time, I have a good six hours, Monday through Friday to work in a quiet house. It’s a tremendous privilege and miracle to pour tea, sit at a desk, type on a very nice computer and write words that thousands of people will read.

It’s not always easy to walk away at 2:00 PM when the bus arrives, but that’s what you do. If I’ve learned anything in my time as an independent worker, it’s to do what I’m doing. When I’m writing, I write. When I’m playing with my kids, I play with my kids. Don’t worry about that project when you’re playing chase in the back yard, because there’s nothing you can do about it right then, anyway.

I try to keep the number of tools I use to a minimum. Here’s what I consider indispensable.

  • A notebook and a good pen. There isn’t an app in the world that matches the flexibility and power of a piece of paper and a pen. Heck, a few lines on the back of a napkin could change the world.
  • Billings from Marketcircle. It’s the only invoicing/time tracking app I need. Both Billings and Billings Touch for iPhone are fantastic.
    Notational Velocity. While I love pen and paper, sometimes I receive information that’s best stored digitally. Notational Velocity is my digital inbox of choice.
  • TextMate with Brett Terpstra’s Blogsmith Bundle. TextMate is my preferred text editor, and the Blogsmith Bundle features several tweaks specifically designed for blogging for TUAW.com. It’s incredibly useful.
  • David Seah’s Printable CEO forms. The Emergent Task Planner is an essential part of my day. I use it to map out what’s going to happen hour to hour, record incidental stuff, track progress on major projects and stay on task.
  • OmniFocus. As I’m not part of a team working on several huge projects, I need a task manager suited to individuals. For me, this is it.

Stephen: A quiet house sounds like a magical place. I’ve forgotten what it’s like.

I like your views on “do what you’re doing.” For me, being on the computer makes that more difficult. As a writer for a major website, how do you manage the never-ending stream of incoming RSS feeds, tweets, IMs and mail?

Dave: I’m afraid I’m a bit old-fashioned. I still use Google Reader for RSS feeds. Mostly because I disliked moving back and forth between an app and my browser.

The good news is that Twitter and IRC have replaced IM for me. I haven’t launched iChat in months. So that’s been eliminated! As for Twitter, growl notifications alert me to any mentions my accounts receive, so I needn’t look at Twitter all day.

Email is another thing entirely. I’d like to say that I only check it at 9:00 AM, noon and 4:00 PM, but that’s not the case. We get lots of tips and other useful bits of info via email all day, so I must keep an eye on it. One thing I don’t do is fiddle with folders, mailboxes and complex rules.

I have one email box, and that’s where everything goes. When I switch over to Mail for a little email triage, I look at each message, decide what it is (tip, reference material, junk, etc.), treat it accordingly (share with the team, file away, trash) and then delete it. Right then and there. Your email client is not a filing cabinet, so don’t treat it as one.

All of that bouncing around between Twitter, IRC, RSS and email is a large part of my day, unfortunately. Yet it must be done. Fortunately, things like Growl and no-holds-barred email triage make it tolerable. Mostly.

Stephen: Sadly, email also has taken over way too much time for me. Oddly, as Twitter and other things have taken off. I think that as more conversational tools have become public and abbreviated, email has become more important.

You’ve shared a lot about how your workflow operates. It sounds like you’ve got some systems in place to keep from drowning. But what drove you to the deep end? You write for TUAW, 52 Tiger and probably personally. How’d you end up behind a keyboard for a living?

Dave: I didn’t choose the life of an independent worker, I had it thrust upon me. In the mid-nineties I was working as an IT Director at a residential school here in Massachusetts. It was a great job and I loved it. The best people you’ll ever meet, lots of fun equipment to play with, decent pay and a “hard” day at work wasn’t hard at all. Just a nice job.

In the meantime my wife and I had our first kid, and I started a blog about the experience, as many have done. About a year in I got an email from the people at Parenting Magazine. They were starting a multi-author blog and asked if I’d be the “dad blogger.” I said yes and it was my 1st paid writing gig.

I was also reading TUAW at the time and they put out a call for bloggers. I applied and was hired. This was back when TUAW was a part of Weblogs, Inc. and Jason Calacanis was at the helm. Before the Aol acquisition.

The more I wrote for these sites the more I enjoyed it. And that was a good thing, because in 2008, my co-workers and I were told that the school would be closed for good in eight months. It took three. One hundred and ten of us lost our jobs.

I went into panic mode and applied for a series of jobs I didn’t get. Subsequent meetings with a career counselor helped me identify tech writing as something I really enjoyed. I spent 2009 (a horrible year I’d love to forget) busting my arse and doing everything I could to earn a modestly respectable amount of money from writing online. Today, I’m almost there.

After three years I’ve learned to enjoy working independently. It’s like tending a garden. Abandon it and nothing grows. Make an effort and you’ll get a few sprouts. Work hard and you’ll have a nice harvest. Maybe. Sometimes. Probably. If you’re lucky.

Stephen: Very cool. Like so many people I’ve spoken too, your desire and ability to write have been matched by life’s circumstances. And (also like many people), you write for multiple sites. Do you ever have to deal with questions about what should be posted at TUAW and what should be posted at 52 Tiger instead?

Dave: Oh man, every day! I’ll take it even further and note that I often get ideas that I’d like to discuss that aren’t appropriate for either venue. Where do they go? Or, do I need to share them in the first place?

Right now, TUAW is my primary focus. It pays the bills, has a significantly larger audience and has been very good to me. I love the people over there and working with them is truly a joy. As news editor, my job is to find news stories that will interest our readers and get them out in a timely manner. It’s fast paced.

At 52 Tiger, I like to take my time. Let a post stew for a few days. Spend 1,000 words or more on a thought. That’s not always possible on TUAW. So I divvy up posts that way.

Stephen: And you bang all those words out on an Apple Extended II keyboard, right?

Dave: You know it. Same one I’ve had for two decades. Once a year I take it apart, give it a good cleaning and put it back together again. I dread the day it finally dies, as I don’t have a replacement.

What I like most about it is the sound. Much like a jackhammer operator who feels satisfied at the end of a noisy work day, I feel I got much accomplished with all that thonking and whacking.

Stephen: That’s awesome. I bought a new-in-box one about 4 years ago and love it. I use my backup — a used one — at the office. I would love to see a how-to video up at 52 Tiger next time you clean yours.

Alright, I suppose we should wrap this up. Any advice to those who want to write full-time?

Dave: Write a lot. Every day, in fact. Even when you don’t feel like it or think you have nothing to say.

Educate yourself. If you didn’t major in English or journalism, take some classes on either or both. Practice makes perfect and it also makes permanent. You don’t want to teach yourself bad habits.

Form your personal Board of Trustees. There are several people I often tap for advice, and they’re invaluable.

Understand that no one cares about you. In your writing, that is. The best writing advice I ever received was this. “No one cares about you. They care about themselves. People want to find themselves in your writing. It must be relatable to your reader. Think of who you’re writing to and write to him/her.”

Give yourself permission to write the shitty first draft (thank you, Anne Lamott). Just getting your idea out will benefit you later. Don’t fret every syllable the first time you sit down. You’ll dive yourself crazy and productivity will suffer. There’s plenty of time to make it pretty.