Dave Caolo

In less than 2 months, I will celebrate 1 year of freelancing with the Mac. It’s been the most educational year of my life. I learned about CSS and PHP, taxes and marketing, faith, patience and the power of being positive. I’ve also seen why the freelancing lifestyle is a cyclical return to the past, and how the Mac is the ultimate freelancer’s tool.

Take a moment and come with the to that little house on the prairie. Yes, I’m talking about Ma, Pa and Laura Ingalls Wilder. When Pa wasn’t saving the day (and making modern-day fathers like me feel inadequate), he was making furniture. It wasn’t Pa’s job to make furniture — there was no time clock to punch or office to occupy for 8 hours a day — it was his work. If you needed a chest-of-drawers, you went to see Pa. Got the flu? Call Doc Baker. Need some pestering done on your behalf? That Nellie Olson is always available. None of them had jobs, but they all created work.

The industrial revolution changed all of that. Instead of laboring at his little house, Pa would have found himself in a factory with a clipboard and a typewriter. He would have worked for the same company in the same physical location for the rest of his entire physical life (this is a metaphorical Pa, of course. Even with this awesome Dad Powers, he couldn’t have lived that long). At that point, Pa would have had a job.

That was the process for decades. Go to the office, perform your job and then go home. Now it’s 2009 and the model that my father adhered to — work for the same company for 35 years, get a gold watch and retire — is dead. Technological advances, automation and overseas outsourcing have eliminated the majority of those production jobs. Freelances like me don’t have jobs, we create work. Just like Pa.

In fact, if you look up the word “job” you notice that many of its meanings — a task, something to be done, an assignment — apply to work both as it existed in the Pre-Industrial Age and will exist in the future. Yet the world is still most often used in the sense that it took on during the Industrial Age — a permanent, full-time position with a single employer. For that reason, I suggest swapping “job” with “work.”

“Job” bears roughly the same relation to “work” that “orange” does to “fruit.” If you go to the store with your heart set on oranges and a bad winter has caused a shortage, you’ll end up disappointed. If you go looking for fruit instead, you’re likely to find a variety of ways to satisfy your taste and appetite.

When a worker has a job, s/he knows exactly what must be done in order to secure a paycheck. The chance that she will do anything beyond what’s required is slim. And why should she? She’s paid do perform her job as described and that’s all she’ll do.

Now, if she doesn’t have a job but is creating work, her choices increase tremendously. She knows her skills and what employers want. She’s free and motivated — heck, required — to move beyond what’s expected and consider what would benefit an employer; what would benefit her; what artful and beneficial way she can apply her skills to solve a problem (fruit, anyone?).

I’m happily creating work and thrilled to be doing it with a Mac which, incidentally, has undergone a transformation of its own.

Years ago, Apple’s slogan was “Think Different.” From the Crazy Ones ad to the Jolly Roger at Cupertino, Apple set their machines apart. No, they don’t operate like every other personal computer and that was the point. Many of us loved the branding. Many more did not. Then something happened while Windows conquered the business world.

Apple offered a free and painless way to run Windows on any new Mac. Suddenly, those machines went from being “different” to being “special.” Yes, they can run that mission-critical, Windows-only software, plus all this other cool stuff. In short, there’s nothing this machine can’t do. It’s the sharpest tool in my kit.

Over the next few weeks, I’m going to write all about freelancing with the Mac. I’ll cover everything that’s been a part of my experience. I hope you’ll read along and get something out of it.

Beautiful. $3 each. Purchase here.

Today I received my first message from Twimailer and promptly fell in love. It replaces the dull, generic and largely useless notification emails from Twitter with informative alternatives. Now, when I acquire a new follower, I see her avatar, bio, name and location. Plus, her following/followers ratio, 10 most recent tweets and a big old “Follow Back” button. No need to launch a browser to decide if I want to reciprocate.

Sign up for Twimailer and use it. It’s a real improvement.

Below is a gallery of screenshots I took this morning of the Kindle for iPhone application [App Store link]. Buying a book via Mobile Safari sucked, but watching it magically appear without having to sync the iPhone or connect it to anything was nice. The text is easy to read and navigation works as you’d expect, though it lacks the eye candy of Classics and the Iceburg books.

For now, you must purchase books and subscriptions via Mobile Safari or your desktop browser. That’s the speed bump here. As soon as users can buy content from the app itself, it’ll be killer.

Here’s our initial post on TUAW. Speaking of which, I’m currently writing an “iPhone eBook Reader Smackdown” for TUAW, featuring Classics,  Iceburg, Stanza, Bookshelf and Kindle. Look for it later this week.

Update: Here’s the Wall Street Journal’s coverage, as well as that from The New York Times and The AP. Here’s a nice side-by-side comparison of the iPhone app and a Kindle 2.

That’s all well and good, but the real fun for me is watching the world’s reaction in real time.

Over the past few months, people have asked me, “…knowing what you now know, would you go freelance today if you had a full time job?” My answer is always “Yes.” But the reason might surprise you.

It’s not because I like working while watching TV in my underwear. In fact, that hasn’t happened yet. It’s because I feel more secure creating my own work than I would at a job.

The model that my dad worked under — stay with the company for 35 years, get the gold watch and then retire — is dead. The Internet is rapidly replacing the middleman. In fact, economist Alan Blinder estimates that 28 million service jobs could succumb to offshoring*. The company I left in 2008 shut its doors after 50 years (I had been there for 15) with 4 months notice. When that happened, I learned that relying on a single source of income won’t fly in 2009.

Now, I’m learning the difference between “having a job” and “creating work.” When I had a job, I sat behind my desk and performed the tasks that would generate a paycheck. No more and no less. It was a drain on me (boredom) and my employer (no innovation from me). Neither of us grew or changed.

The benefit of creating work is twofold. First, I’m never bored. I get to move from one interesting project to another, each with its own challenges and rewards. Additionally, my employers benefit because, if I’m going to survive, I must continually think of new things to offer. As Michael Scott would say, “It’s a win/win/win situation.”

Working as a blogger, I’m very lucky in that I have no overhead, employees, inventory or office space. All I need to do my job is an internet-enabled computer, some software and whatever brain cells my children haven’t destroyed. Still, there are plenty of opportunities to save money. Here are a few of my favorites.

Find free Wi-Fi

Ideally, I’d work from home every day. The Wi-Fi is already paid for, as is the heat, electricity and food. However, I must occasionally put pants on** and go outside. Be it for a meeting or a need for adult interaction, sometimes I’m tempted to go to Starbucks, the Chocolate Sparrow, etc. When that happens, I end up at the library.

I’ve written about this before, but I love working at the library. The Wi-Fi is free, there are plenty of wall sockets to plug into, it’s quiet, the tables are huge and all the reference material you’d ever want is within arm’s reach. When I’m at a coffee shop, my thoughts are competing with the din of music and nearby conversations, while my wallet begs for a drink, a muffin, and so on. Now, if you really dislike the library idea …

Find cooperative office space

These are starting to pop up all over the country. For a very small fee, you can get access to a desk, internet, printer and often more at a cooperative office. Plus, you’ll have a chance to do some networking and meet like-minded people, all without the full cost of renting an office the traditional way.

Free or less-expensive software alternatives

This one is quite straight forward. There’s a free or low-cost alternative to nearly every piece of software you can think of. For example, I haven’t used Microsoft Office in many years. Instead, I use ThinkFree Office. It’s absoutely free and exports/imports Word, Excel and Powerpoint documents beautifully. Google Docs is another popular choice.

Photoshop.com offers free image editing that’s more comprehensive than you might think, and a free PBWiki account will help you keep everything organized.

The Latte Factor

In his book The Automatic Millionaire, David Bach talks about “The Latte Factor.” Basically, he encourages people to consider what they spend on little things. Sure, four bucks for a latte is nothing. But drink one each weekday, that’s $80/mo. or $960/year.

Now, I’m not suggesting that you can’t enjoy a coffee now and then. But there are more economical ways to enjoy it. My vice is tea. At the coffee shop, it’s a couple of bucks for a cup. Brewing it at home, I pay $0.62 per cup.

So there are a few of my favorites. I hope you found this useful.

———-

*Mannes, George (2009, February). Be prepared for the long haul. Money, 87-89.

**OK, I lied.

A few enterprising Drupal developers have built a convincing copy of 37signals’ project manager Basecamp, and they want to tell you how to do the same. It definitely looks and feels similar. We’ll see how long this lasts.

What is the one thing that prompts us to subscribe to a weblog? It’s not a beautiful design, thoughtful layout or frequent updates; it’s the quality of the content. I return to blogs that offer something valuable in exchange for my time.

Quality posts attract readers. Unfortunately, great ideas don’t appear out of thin air. The good news is that they’re easier to generate than one might think. Here are six things I do to help me consistently produce super posts.

1. Notice Everything
A basic concept, but not as easy in practice. Recently, I became frustrated while unsuccessfully brainstorming ideas, until I realized that the very experience I was having would make a great post – the post you’re reading now. It was only after I had considered an experience that I would typically ignore that I became productive. Half an hour later, I had six great ideas for feature-length posts. To use a photography analogy, I was using the macro lens when I needed the wide angle.

2. Be Prepared

The American Boy Scout motto applies to bloggers, too. As noted above, almost everything we encounter – a chocolate milkshake, a walk in the woods, a conversation with a friend – can trigger a great idea. Compensate for this unpredictability with preparedness. I have a stack of index cards and a pen with me at all times, so I can immediately jot down any idea.

But even that’s not bullet-proof. Recently, I was listening to NPR in my car when I got an idea for my (now defunct) daddy blog. While I could have managed to write it down at 40 m.p.h., I used my cell phone to leave a voice mail message at my office. I captured my idea, and no one got killed.

3. Talk With a Variety of People

I consistently discuss certain topics with certain friends. One guy is my “geek buddy” – we talk about computers and technology. I discuss books and writing with my “literature buddy.” While I enjoy their company, things get really interesting when I’m discussing a novel topic with someone outside of my daily experience.

When I moved to Boston at 18, I was alone in a new city. Eventually, I befriended many people whose experiences were much different than my own, and my interactions with them changed me tremendously.

Now, I’m not suggesting you up and move to improve your blogging, but the internet represents as diverse a community as you’ll ever find. Look beyond your bookmarked blogs. Visit new message boards and see what people are saying. Flickr’s “Explore” feature is a great way to do this. In fact, that’s how I met a friend who works on a chimpanzee reserve in Africa. Poke around the global neighborhood and see what you’ll find.

4. Create a “Blogging Only” Workspace

Psychologist B. F. Skinner is the father of behaviorism, or the study of why and how people do what they do. Critical to his work was the exploration of how a person’s environment can influence their behaviors. With this in mind, I’ve set up a “Blogging Only” workspace in my basement.

It’s simply a small room with a computer, a long table and a printer. Whenever I write, I do it in this room, and only this room. I’ve conditioned myself to associate this area with writing, so my brain goes into “writing mode” as soon as I sit down. Call it a “kick start.”

Of course, you don’t need a dedicated room. A cozy corner of your kitchen, the back porch, your favorite coffee house…the location itself doesn’t really matter. The important thing is that you use it consistently. Soon you’ll be able to achieve the proper state of mind just by sitting down.

5. Step Away From the Blogosphere

The blogosphere is a tremendous source of inspiration. However, “information overload” is very real! Time spent away from the computer is just as beneficial as reading inspirational posts. Do whatever you like – run, take a walk, have coffee with friends, listen to the birds in the back yard – to clear your head. Once we de-clog our brains of emails, chats and so on, creativity can flow freely.

6. Create a Crappy First Draft

As a student, I learned that anything I commit to paper had better be worth reading. I wrote and re-wrote one paragraph before starting the next. The flow of my writing suffered, and I lost useful ideas to a flurry of obsessive editing.

Today, I permit myself to write “The Crappy First Draft.” The goal is to get my ideas and intentions written…damn the torpedoes! There will be plenty of time to go back and make it pretty. Allow yourself to write a dreadfully awful first draft. During your re-writes, you’ll be glad you did.

Here’s a very simple trick that’s been serving me well this week. I made a “Postable” smart folder in The Hit List as pictured above. Now, whenever I get an idea, email or inspirational link that could become a post, I add it to The Hit List with the Quick Key Entry shortcut, tag it with “/postable” and it’s ready and waiting the next time I lauch WordPress.

Web-based checklist generator Printable Checklist is as simple as can be. In my experience, the best productivity applications mimic the simplicity of paper. Printable Checklist is as close as it gets.

[Via Swiss Miss]

Let me tell you about about my childhood.

There is a small, shoebox-shaped house in Scranton, Pennsylvania with faded vinyl siding and an under-performing rose bush in the front yard. Twenty years ago, it was occupied by my typical American family: middle class, happy enough, God-fearing and terribly disorganized.

Consider the kitchen. Open the cabinet to the right of the refrigerator, just above the pink laminate counter top, and you would have found my mother’s recipes. Unlike your mom’s collection, Carol’s never saw the inside of a cookbook. Instead, they hung from the back of the door with yellowing strips of tape.

A Hellman’s mayonnaise label with a potato salad recipe dangled next to my grandmother’s hand-written instructions for stuffed squid. There were pages ripped from Family Circle magazine, supermarket hand-outs, 3×5 index cards, torn business envelopes with their postmarked stamps intact … anything flat enough to write on and light enough to stick to a pine cupboard door  was used to capture a recipe.

Most bore stains acquired in the line of duty. A sheet of yellow legal paper held a recipe for lemon squares as well as greasy butter stains and a smudge of hardened baking flour about the size and shape of a postage stamp. “David, hand me that sheet of paper,” my mother would say, thrusting her egg-y fingers at me. Another Christmas, another batch of lemon squares and another crop of stains. Buy the time I was in high school, the recipe was nearly illegible.

While the “fly strip method” of recipe storage keeps everything accessible, it’s a poor filing system. Linguine with anchovy paste rubbed up against blueberry cheesecake, which is something that should never happen, not even in print.

Like most messes, my mother’s organizational style had the tendency to spread, like an invading army, or syphilis. The inside of my dad’s garage looked like a yard sale had vomited, and the state of the basement was something I won’t even mention.

What all this means is that I’ve got chaos in my blood. It didn’t become problematic until I started working for myself. Those painful moments of realization — “Oh, I really need to …” — were becoming more common, and always at the least opportune times. Remembering to tell the cable company that I’ve been issued a new debit card is of no use at 60 m.p.h. on Route 3.

Thankfully, I found David Allen’s Getting Things Done (or “GTD”) and it changed my life. When you’ve got a trusted system in place, your brain stops pestering you. When you’ve got your pending tasks sorted by context, you relax. What’s more, you get stuff done (I think that’s where he got the name).

One of the crucial aspects of a GTD system is the ubiquitous capture tool. Basically, Dave wants you to “capture” any thought, task, or “open loop” as he calls them for later processing — which is a fancy way of saying “write shit down.” It’s simple, low tech and very effective.

hPDA

It’s also the part of GTD that’s the most fun and the biggest pain. At least for a geek like me. One of the Seven Great Truths of Geekhood is that we’re always willing to try a new system if we think it’s better than what we’re currently using. Dave leaves his readers’ choice of ubiquitous capture tool completely up to them, and that’s where I got into trouble.

Initially, I went out and bought a snazzy Palm Tungsten E2. With a calendar, contacts app, notepad and software synchronization, I figured it would be the ultimate. A month later, I realized I was using it to store lists. A $200 PDA to hold lists. I sold it and created a Hipster PDA, or hPDA, as described by the great Merlin Mann (by the way, Merlin has the best hair on the Internet. He knows it, too).

The hPDA, for the uninitiated, is a bunch of 3×5 index cards held together with an office clip. That’s it. I brought mine to the next level with some color coding and the D*I*Y Planner templates. My hPDA was tidy, cheap, disposable, recyclable and simple. Occam’s Razor in  my pocket. With a tiny, write-anywhere Fisher Bullet Space Pen, my hPDA (which I nicknamed “Shirely,” just to give it a little more personality) was as awesome as a dozen index cards could be.

Mole Skinned

Then it happened. I was tempted by the legendary notebook of Hemingway and Picasso. My head swelled with my action lists whenever I produced my slick notebook and slid back the elastic binding strap, all the while scanning the room for anyone else in “the know.” Fellow notebook aficionados would nod approvingly at the guy writing important things in the same notebook used by one of the world’s most famous alcoholics and a psychotic, self-injurious painter.

I adopted an elaborate system of tags, numbering, incantations and logic puzzles to “hack” my Moleskine for GTD. When the voice inside my head told me, “This is kind of annoying,” I rebuked it. “Oh hush,” I’d say, “and help me remember why all of the odd pages are written in blue ink.”

The other hassle was that I couldn’t easily discard spent pages. When an index card ran out of white space, I tossed it. No clutter, no mess. The Moleskine didn’t allow for that.

Field Notes

Next, I bought a 3-pack of Field Notes brand notebooks. For me, these trump the Moleskines. While the Moleskine gives off a certain air, the Field Notes notebook is a utilitarian tool ready for duty. It says, “Let’s work,” not “Sketch that sunset.” Plus, it’s thinner and less bulky in the pocket.

Still, I was still subject to the same cumbersome system of analog tagging and linking. Ultimately, I’ve gone back to my original system — a dozen index cards in my pocket.

One of the great tennants of GTD is “Capture-Process-Organize-Do.” The other is “To each his (or her) own.” David’s bare-bones system is flexible enough to accomdate any work style or process. This is what works for me. Here’s hoping you found it useful.