Dave Caolo

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.

Valentine bentos for the preschool set

Sweet Valentine’s Day mix tape

Sketchbook for web designers

There are more than 15,ooo apps in the App Store. I’ve tried many, reviewed even more at TUAW and kept a few. Here are those few.

We’re going to explore these by page. That is to say, I’ll first write about the (non-Apple) apps that live on my iPhone’s home page. Next, the apps on page 2, and so on.

Once that’s complete, I’ll list the apps that are on the verge of getting cut and finally the ones I paid for but no longer use.

But first things first. Here are my “Page 1 Apps.” Check back for page 2 soon.

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.

As sad as it is to see Joaquin on what appears to be a downward spiral, it’s always fun to watch Letterman when he’s irate with a guest.

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.

Official Tooth Fairy Kit