Dave Caolo

Over at my professional site, DaveCaolo.com, I describe the three simple ways I manage those infuriating office interruptions. It’s easier than you think. And no, “run screaming from the building” is not on the list.

Just yesterday I posted my professional goals for the week. Credit good karma, motivation or that giant bag of crystal meth I smoked this morning, but I’m beating this sucker up like Iron Mike Tyson. Here’s an update

• Order new business cards (2 points) Score! +2
  
• Complete website (2 points) Score! +2
• Publish WordPress video (2 points) Score! +2
• Write new blog articles (2 points per)
• Draft new video series (2 points)
• Pitch my presentation “Blogging for Artists” to local galleries (2 points) Score! +2
• Connect with local members of the tech community (1 point)
• Mail proposal to Client A (10 points) Score! +10
• Land Client B (10 points) Score! +10

Plus, I got five posts up at TUAW today. Sweet Mother of Mary, I’m on fire. Here’s to organization, discipline (turn Twitter OFF once in a while) and the motivation offered by a monthly mortgage.

I use Backpack by 37signals for personal project management (the electronic arm, that is). Recently, I completed a project (go, me). However, I didn’t want to delete the project page and all of its files. Nor did I want to stare at it in the middle of my projects list every day.

So, I decided to “archive” it. By renaming the page with a “z” as the first character, it dropped to the bottom of the list in my sidebar. This is how I’ll deal with all archived projects in the future. The page continues to exist as it was when the project was open — all files, history, communications, etc. in place — but it’s no longer grouped with my open projects.

As David Seah points out, CEOs focus primarily on actions that move their companies forward. As an easily-distracted freelancer (New iMacs are out? Cool!), I need assistance in identifying and accomplishing these goals.

So, I use Dave’s Concrete Goals Tracker (CGT) forms. Each Sunday, I sit down and list the actions I’ll take in the next six days to move my business forward. The CGT makes that fun by assigning point values to different categories of activities.

For example, life-sustaining billable work (like signing a new client or contract) is worth 10 points. Concrete planning or accounting is worth 5, acts of self-promotion are worth 2 and relationship maintenance is worth 1.

I thought I’d share the goals I’ve created for this week with you. This weekend I’ll tell you how many points I scored.

• Order new business cards (2 points) Score! +2
  
• Complete website (2 points)
• Publish WordPress video (2 points)
• Write new blog articles (2 points per)
• Draft new video series (2 points)
• Pitch my presentation “Blogging for Artists” to local galleries (2 points) Score! +2
• Connect with local members of the tech community (1 point)
• Mail proposal to Client A (10 points) Score! +10
• Land Client B (10 points) Score! +10

Check back this weekend. Now, back to work!

Update: Nick recently released Put Things Off for iPhone and iPod touch [App Store link], a mobile task manager that I love and recently reviewed on TUAW. What follows is an interview I conducted with Nick in April of ’08.

We live in a world obsessed with technology. Consider how quickly things move — twenty-five years ago, we had thirteen channels on TV (most of them snow), the Mac had a 8 MHz processor and the lucky among us owned a typewriter. Today, keeping up with the latest and greatest is a full-time job.

We’re also obsessed with productivity. Worse than that, we’re obsessed with being obsessed with productivity. There’s got to be a point where a person says, “Enough.”

A few months ago, I discovered Put Things Off, a productivity blog by Nick Cernis. It’s different than most — Nick writes about simplicity in a way that appeals to freelancers and office workers. He recently release his first eBook, Todoodlist* which I enjoyed very much.

I had a conversation with him about the book and our relationship with technology in general, which I’ve published below. Enjoy.

» Read the rest of this entry «

It’s important to feel productive and useful. However, there’s an erroneous assumption that “productive” is always synonymous with “busy.” The image of an office worker who can simultaneously handle a phone call, fire off an email and staple the new cover to his TPS Report is enviable. “Multi-tasking” is a buzzword which suggests a peak state. We should all be so busy, so motivated, so … productive.

He’s getting things done for sure. But I’d argue that the most productive part of my week is when I appear to be doing the least.

Each Sunday morning I sit at my desk with my notebook and pencil. My iPod plays my Weekly Review Playlist and a cup of hot tea silently lets off steam.

My computer is off. Nothing is printing, beeping or chirping. It’s my favorite part of the work week, and I’m sharing it with you here, including a free download of my weekly review music. Enjoy!

Project Status

Each of my open projects has a folder in my Support drawer, and each folder contains a project overview sheet, which lists the overall goal and all action steps that must be completed before I can mark the project “done.”

I’ll pick the action steps I want to accomplish during the upcoming week and move them to my notebook, and cross off the steps I completed during the past week. I repeat this process for each folder, and when I close the last one, I’m done.

Delegated Items

If any items I’ve delegated remain unfinished, I make a note to contact the appropriate person on Monday.

What’s in the inbox?

Once I’m finished reviewing my projects, I review my inboxes, with are

1. My notebook It never leaves my side and captures all the verbal requests I receive, things I hear on the radio, etc.
2. Email I go through all my messages one at a time, decide what needs to be done (if anything) and act accordingly.
3. Voicemail A necessary evil (for now!).
4. Physical inbox Handouts from my daughter’s preschool, paper mail, etc. are piled in my plastic inbox during the week. Each is processed in turn and an action step (if any) is moved to my notebook.

At this point, I’ve done several things. First, I know where I stand on all of my open projects. That’s a tremendous feeling.

I’ve identified my goals for the week. I’m the kind of person who likes to be told, “Here’s a list of exactly what I need you to do.” This way, I give myself such a list.

Finally, I’ve crossed off many completed actions. That’s an even better feeling.

The Music

As a special thank-you to all my readers, I’m sharing my Weekly Review Playlist. You may download each track individually or as a whole. I hope you enjoy it. Now, turn off your computer, find a quiet place, make a lovely cup of tea and experience the most productive two hours of your week.

Weekly Review Playlist — 30MB

1. 3 Plus 4 – El Ten Eleven
2. Dot 2 – Gregor Samsa
3. Lorge – El Ten Eleven
4. My Only Swerving – El Ten Eleven
5. No One’s Gonna Love You – Band of Horses
6. The Thief – Jeremy Larson
7. Jezebel – Iron & Wine
8. Rise Up With Fists! – Jenny Lewis and The Watson Twins

Every weekday morning, my wife drives her clunky old Nissan to work. At the first stoplight, she turns into the Hess parking lot, walks inside and gets a coffee from Dunkin’ Donuts. It’s the kind of daily non-event that that doesn’t warrant a mention.

Until this morning.

“Do you know Dunkin’ Donuts sells pizza now?” she asked.

“Pizza?” I said.

“Sandwiches, too. Not the breakfast sandwiches, but hot flatbread sandwiches. Turkey club, that sort of thing.”

“Well, that’s crazy,” I said.

“I know!” she said. “Who wants a Dunkin’ Donuts pizza?”

Several weeks ago, I was stammering and stuttering in a room full of small business owners, a bank manager, a CEO, a public accountant and my career counselor. “Will you explain your business idea to me once again?” the accountant asked.

“Sure,” I said as a small BB of sweat rolled down my spine. “I do technology counseling for home and business, technology writing and marketing through weblogs.”

“Wow,” she said. “That’s a lot of stuff. Which one do you do well?”

Ouch.

This was the culmination of a week-long business class. After forming a basic business plan, financial projection and so on, our assignment was to speak for three minutes about just what we intend to do. Several of the students nailed it. I wasn’t one of them.

Later, when the group was mingling, exchanging business cards and eating donuts, the accountant approached me.

“Good job up there,” she said.

“Oh, please,” I said. “I think it’s too early in my ‘career’ for me to be in this class.”

“No,” she said. “It’s the perfect time. You’re full of good ideas and enthusiasm. That’s great. You just have too many ‘buckets.’ When you told me what you do, I thought, ‘Here’s a guy who is mediocre at three things.’ I want to know that you’re an expert at one thing.”

In other words, I was selling pizza at Dunkin’ Donuts.

For all I know, the pizza at Dunkin’ is the best in the world. Their flatbread sandwiches might surpass those at my favorite deli. But I’ll never find out, because I won’t try them. My perception of Dunkin’ Donuts is that they make great donuts. They taste good, they’re fresh (in the morning anyway), they’re consistent and inexpensive. I know that if I buy a Boston Creme from Dunkin’, I’ll love it.

But pizza? No. If I want pizza, I’ll go to Carmine’s. Flatbread sandwiches, The Corner Store. They’re the experts at pizza and sandwiches, respectively.

It’s easy for ambitions freelancers to inadvertently market themselves as Dunkin’ Donuts selling pizza and sandwiches. You’ve got killer ideas plus oodles of talent and confidence. That’s all wonderful, but consider your customers’ perception of that same far-reaching ambition.

I once heard someone describe himself as a “New media freelancer.” My immediate thought was, “I have no idea what that means” — and I’m a techie! Imagine you’re the owner of the General Store or the director of the tri-county library system. You may very well benefit from the services of a new media freelancer, but you probably won’t because that confusing title won’t get him in the door.

The lessons I learned are

1. Identify your niche. I’m an IT guy.
2. Describe it in plain language. I help people and small businesses make computer repairs, set up networks, make purchases and get the most out of their technology with one-on-one coaching.
3. Avoid “also-rans.” Again, it’s not easy, but it’s crucial. Consider your client’s perception of what you actually do.

I hope this was helpful. Good luck!

As I read Wired Magazine’s interview with Jason Fried and David Heinemeier Hansson of 37signals, as well as their response, I was struck by a line written by Wired writer Andrew Park:

“Complexity is a necessary byproduct of the modern age.” Wow, that’s completely wrong.

This idea comes from the erroneous notion that the tools of technology are complicated, and using them effectively even more so.

Plastic “In” and “Out” boxes gave way to file cabinets, then microfilm, then automation, databases and eventually, the bane of human existence, enterprise software! Business is big, fast and important; only complicated, intricate software can possibly aid the business world.

Wrong. All we’re talking about here is people. People talking to people. That’s it. Those people use tools, and there’s nothing they can’t do, from negotiating a billion-dollar deal to designing a better mouse trap, with the simplest tools of all – a piece of paper and a pen.

A blank sheet of paper is pure potential; Nothing is more flexible. David and Jason understand this, and that’s why their products – especially Backpack, Basecamp and Writeboards – look like a fresh sheet of paper. Write something down, move it around, cross things off, invite others to add their own scribblings. Any of their products are just as effective as software that costs thousands of dollars per installation. More so, even, because people will actually want to use them.

I’m not IBM or Coca-Cola, but I manage my entire life as a father, IT director, independent tech consultant, technology writer and husband in Backpack. Soup to nuts. I’ve tried a slew of other products and none of them did what I want more successfully than Backpack.

The word “technology” simply refers to machinery and equipment developed for a specific purpose. Some tools of technology are complicated, like atom smashers and the space shuttle. Most aren’t, like hammers and potato peelers. Somehow, “technology” became synonymous with “computer”, and computers are highly complex and mystical machines that only the most intelligent among us can operate, right? Wrong.

The tools we use to communicate and manage our lives aren’t restricted to an elite coven of über-nerds or business people.

Or, at least, they shouldn’t be.

Meet Sandy, your new assistant. She efficiently manages your appointments, reminders, daily scheduling and more. She’s always on email, of course, but she’s also into Web 2.0 apps like Twitter and Jott, and likes to text as well. Even though English isn’t Sandy’s first language, she understands it very well. Best of all, she works for free.

One more thing: Sandy isn’t a person. She’s a bit of software on a server overseen by Values of n, Inc. I’ve been using Sandy for some months now and just love her.

Did you see what happened there? I called Sandy “she” and “her.” Not because I’m trying to be cute, but because it feels weird not to. Even though Sandy is really just a front-end for Stikkit, the web- and email-based task manager from Values of n, Inc., the pleasant emails and reminders she it shares seem as if they were written by an actual person. A friendly one at that.

It’s simple to use, effective and like I said, free. Here are some of the things I love about Sandy.

There’s nothing new to learn

If there’s one criticism of productivity geeks that’s entirely accurate, this is it: We spend almost as much time fiddling with our systems as actually doing our work. The problem is that we’re geeks, and a geek will always try something new if he believes it’s better that what he’s currently doing. That’s The First Indisputable Truth of Geekdom.

Couple that with the recent proliferation of productivity software, and you’ve got a lot of distracted, hPDA-wielding nerds.

But I don’t want to learn new software just to get things done. I’m old and crabby, and rapidly getting older and crabbier. Sandy, being lovely and accommodating, makes no such demands. All I’ve got to do is send an email.

Each account generates a unique email address. Anything sent to that address – like an appointment or a reminder – is filed away by Sandy. I spend a lot of time working on the web, so my email client is almost always open. When the spirit moves me, I just compose an email and hit “Send.” That’s it.

It’s appealing

A person is more likely to use something that she likes. I write things down all day because I must in order to remember what I need to remember. I make these notations in a Moleskine because I really like them. That way, I’m more likely to write something down; I’m happy to have an excuse to play with my notebook.

The same goes for my computer. I use a Mac because I like the way it looks and and functions. I’ve got to use a computer to get much of my work done, and since I love my computer, I’m eager to use it.

This is why Sandy works, too. All day long I receive pleasant emails and text reminders that say things like, “Hey, Dave. Here’s what I have scheduled for you today … Be well, talk to you soon.” I mean, come on. That’s just nice. Even my kids aren’t so consistently pleasant:

“Hi, honey. What did you do in school today?”

“I don’t know.”

“Well what did you talk about?”

“I don’t know.”

“Awesome. Good talking to you.”

Many ways to solve a problem

I’ve already shared The First Indisputable Truth of Geekdom with you. Here’s the second. We like to have many ways to solve a singe problem. Ask any geek “What’s the best way to set up a brand new, off-the-shelf computer?” and you’ll see what I mean. Sandy offers this flexibility in spades.

There are several ways to get information to Sandy. The simplest is email, which I’ve already explained. Next is Twitter.

To get started I, added Sandy as a friend (her username is simply “s”.) Next, I added my Twitter username to Sandy’s Twitter preferences. I’ve also opted to have Sandy send me reminders via direct message.

On the Twitter side, I’ve set things up so that I receive direct messages via SMS, which is super handy. With my iPhone, I can schedule appointments and receive reminders from Sandy anywhere.

Once everything is set up, Sandy regularly polls Twitter for direct messages. For example

• d s reminder leave in 5 mins
• d s r go for a walk in 15 mins (“r” tells Sandy that you’re requesting a reminder. There’s also “u” for update, “f” for forget and “i” for invite)
• d s l tomorrow

You can also Jott to Sandy. I don’t use Jott, but it looks pretty interesting. Basically, it’s a voice-to-web service that converts your phone messages to text on the web. After following these set up instructions, you can direct a Jott call to Sandy, no typing required. That’s pretty cool.

Receiving info from Sandy

Every morning, Sandy sends me my Daily Digest, outlining what I need to do. I also receive messages via SMS and Twitter.

Sandy is a rare beast: Productivity software that isn’t bursting with features and functions that I’ll never use, or that actually hinder productivity. No menus, icons, toolbars, drawers, smart folders or any of that. Just send and receive.

If you’re a person who 1.) Needs to remember to do things and 2.) Understands how to use email, you ought to sign up for a free Sandy account. I’m sure you’ll love it.

This is the first in a monthly series of posts intended to review my experiences in 2008, one month at a time.

January’s lesson: “The simplest way to make a coyote is to learn how to make dust and then put a coyote on it.”

2008 began with my 37th birthday. I received some great gifts, including a Jesus Christ I’m Forty And Still Can’t Get My Shit Together, a You’re Not Forty But Close Enough, a When Will I Be Able To Just Buy A Damn Concert Ticket Without Having To Save Up First and, from my wife, a Please Stop Dressing Like A Homeless Teenage Runaway Because You’re 40 Now And Stop Sucking In Your Stomach Because You Aren’t Fooling Anyone.

So that was good.

Last October, my coworkers and I were told that we’d be jobless by December of ’08. In January, that date moved to July. Today, it looks like June. After going through all the stages of Maslow’s Hierarchy of Holy Shit I Just Lost My Fucking Job, I set up an appointment with a career counselor. If you haven’t done this, you should. It’s kind of like therapy; you sit in a clean, well-lit room with jade plants and Asian artwork and talk with a bookish woman who is infinitely smarter than yourself but does a good job of not letting on that she knows it.

In a few weeks, I learned some incredible things.

• Work and fun needn’t be mutually exclusive. I was raised to believe that work is what one does to pay bills; something to be endured, not enjoyed. My parents were vocal about hating their jobs and I’ve pretty much hated all the jobs I’ve had (though it’s difficult to enjoy scrubbing spent oil off of the floor of a Sunoco garage at 11:00 PM).
• Having a job isn’t the same as finding work. When you’ve got a job, you expend the least amount of effort possible to ensure a paycheck. A job stifles creativity and potential benefit for the employer. A person who is finding work actively creates opportunities, situations and projects that benefit himself as well as others. The opportunity for creativity and fulfillment surge.
• The 9-5, 40 hour work week is dead. In my father’s day, you worked for a given company for 35 years, got the gold watch and then retired. That was your career. Today, that model is out the window. A person’s career is her collected body of work. Consider your career as a student. It starts in pre-school with crayons and singing and ends in college or graduate school. That’s quite a difference! But the same career.
• The Blueberry Creme Frappuccino at Starbucks is the greatest thing I’ve ever had in my mouth. Seriously, have you tried one of these? If something tastes this good…hell, I’ll take the pot belly.

My children continue to age. The boy is now two and the girl is four. They say that a person’s personality is pretty much intact by the time they reach 5 years of age, so the girl is set to rule a third world country with an iron fist. Her favorite activity is grabbing her brother’s T-shirt at the neck and pulling him forcibly to the ground.

She’s very good manipulating me into giving her several snacks per day, yet she’s utterly unable to flush the toilet, evidenced by the small piles of “raisins” I find in there time and again.

Two couples I know are having marital trouble, and it’s sad and scary. I’m usually the last one to go to sleep at night, and when I sneak into the kitchen to get an iced tea (and pretend it’s a Blueberry Creme Frappuccino…seriously, you really need to order one), I’ll go into my kids’ bedrooms and just watch them sleep. My girl with the stuffed cow I won for her at Hershey Park before she was even born; my boy’s little blond head barely visible beneath the fleece Hot Wheels blanket.

I feel so much love for them, and for my wife. As a mother, a full-time teacher and a partner she is unbeatable. After 10 years together, I love her even more than the first day I saw that summer sun shine right through her flimsy dress, giving me a glimpse of what the Good Lord had given her.

Speaking of The Lord, I made some spiritual gains as well (I know, right?!), thanks to one of my great heroes, Chuck Jones.

A few weeks ago I came across this video of Chuck sketching Wile E. Coyote. It’s cool to watch him draw, and even more fun to listen to him narrate the process. For instance, Chuck said that he likes to draw Wile E. with a fork in his hand, “…just in case.” What an optimist. He also said something that made me stop in my tracks.

“The simplest way to make a coyote is learn how to make dust and then put a coyote on it.”

Of course. When I learned about my company closing, and my friends’ troubled marriages, I panicked. “I need the perfect marriage and job. Now.” I thought. I immediately sought the security of a 9 to 5, widget-cranking job, just to keep the paychecks coming. So, I networked. I emailed people I knew, tossed business cards around and so on.

Then I started to re-think my attitude about work. I actively sought out like-minded individuals. I built a small community of people I really like, creating real relationships with them.

Meanwhile, I talked to my wife directly and honestly. “How are we? How are you? What can I do? Let’s name one cute thing the kids did each day before bed.”

Then things started to happen. Some work here. A job there. A friendship, a colleague and a new experience. My wife has told me that she feels better about our marriage now more than ever, and I feel the same way.

I had kicked up the dust, and put the coyote on top with no effort at all. I had never made a coyote before, but it sure was easy to do.

Here’s to a great February. Thanks for reading.

Now go kick up some dust.

Thanks to 37signals for pointing out the Chuck Jones clip.