by Dave Caolo

As an independent worker, you’re free from office politics, a pre-defined work schedule and the drudgery of “work for work’s sake.” Sounds good, right? It is. In fact, that’s why many of us go independent.

Freelancing also means that we’re responsible for the aspects of business that an employer would typically handle for us. Among them are what I call the big three. In this post, I’ll look at each and describe how I handle them.

Every freelancer is a technician, an entrepreneur and a manager.

Technician

For many of us, including me, this is the easy one. The technician is the one who does the work. A graphic designer is in “technician mode” when she launches Photoshop or Illustrator. For a writer it’s sketching an outline or opening a text editor. An IT pro wears the technician hat when designing a network or setting up hardware.

In other words, it’s doing the things we love to do. In fact, it’s what we’d spend all of our time on if we could.

And there’s the danger.

I’ve known too many independents who were content to watch their lives pass buy through an office window. We became freelancers, in part, for the extra freedom it affords, right? Yet many of us find ourselves behind the desk more often than not. How does this happen? I see three causes.

1. Fear: Fear of losing out to the other guy. Fear of disappointing a big client. Fear of karmic retribution brought on by not showing enough hustle. 

Here’s the good news: We’re all afraid. Yes, I want to land that high-paying gig. I also want to ensure that I’m fresh enough — physically and creatively — to handle that job when it arrives. If there’s something we should fear, it’s being too wiped to manage the dream gig.

2. Poor work/home separation: The best thing I ever did was abandon my home office. Not that there was anything wrong with it, I loved it. But with it came the temptation to work “just for a minute,” whenever I had some free time. A minute became an hour and an hour became Saturday afternoon. And Sunday morning. And then Sunday evening. 

Today, I work at the library. It’s clean, well-lit and comfortable. The Wi-Fi is free, as is my seat at the large, window-side table. Plus, all the reference material I could ever want is an arm’s length away. Best of all, it’s not home. When my work day is done, I can walk through the door, close it behind me and leave “work,” both physically and mentally. It feels great to go home knowing my day is done, and that I needn’t address any outstanding to-do’s until the next day.

3. The 9-5 hangover: Like many of you, I spent many years in a 9-5, full-time job before going independent. Eighteen years, in fact. During that time, I became indoctrinated in that culture. The world has agreed to shuffle papers between 9:00 AM and 5:00 PM, and that’s what I did, whether it was productive or not.

Shortly after becoming a full-time freelancer, I suffered from what I call “The 9-5 Hangover.” Specifically, I felt guilty if I didn’t fill every minute between 9:00 AM and 5:00 PM with some sort of work fidget, like checking my calendar, reading email, fiddling with my phone and so on. 

Fortunately, this type of hangover has a cure.

Consider this: What’s your time worth? Let’s say you make $50,000 per year. That’s about $25/hour. Suppose you check your email every 10 minutes for 2 minutes per check. That’s 6 instances per hour for a total of 12 minutes spent per hour looking at email.

You’re spending 12 minutes per hour not working on a project, not performing life-sustaining work ‚ & essentially not earning money.

At $25/hour, you’re time is worth $0.41/minute. Multiply that by 12 minutes per hour and you’ve lost $4.92 per hour. If you work an 8-hour day, you’re down $39/day. Still sound good? 

Now think about this: If you check your email every 5 minutes, you’re doing so 24,000 times per year.

Hangover: Cured.

Entrepreneur

In addition to being a technician, every freelancer is an entrepreneur. It’s fun to think of new ideas, new strategies, new projects. I love this aspect of being on my own. It also gets me into trouble.

More than once (OK, much more than once) I’ve gotten excited by a hot new idea. So much so, that I acted on it right away. I’m sure you know where this is going: flat-on-my-face failure. Without proper planning, thought or consideration, these projects were doomed from the start. I let my enthusiasm get ahead of me.

To combat this, I’ve adopted an aspect of David Allen’s Getting Things Done (GTD) methodology called the Someday/Maybe List. For me, it’s a piece of notebook paper that lives in an envelope inside a cabinet drawer. On the list are all of the great ideas I’ll address someday. Maybe.

When lightning strikes, I write it down on the list and file it away. This does two things. First, it allows me to capture the idea. The knowledge that I have it written down lets me move on to other things.

It also puts the idea back in front of my face at regular intervals. As a part of my weekly review routine, I pull out the Someday/Maybe list and review each item. As I do, I ask myself, “Is it time to move forward on this?” If the answer is yes, It goes into a R&D folder. If the answer is no (it usually is), it goes back in the drawer for another week.

Using this method, I’m able to capture good ideas, acknowledge my entrepreneurial spirit and not get in my own way.

Manager

The manager handles the nuts and bolts of business. S/he keeps both the entrepreneur and the technician in line and on schedule. The manager looks over the financials, books and so on.

The manager bores me to tears.

I’ll admit that this is the one aspect of freelancing that I dislike. Still, I tackle managerial duties through a trusted system and external support.

For any freelancer, it’s crucial to have a trusted system. This is how you’ll track what needs to be done and ensure that it happens in a timely manner. For me, it’s David Allen’s Getting Things Done. GTD has changed my professional life. Without getting too far into it, I’ll just say that GTD lets me feel in control even when there’s an overwhelming amount of work to be done.

GTD may or may not work for you, and that’s fine. The important thing is to adopt a system that you like, that you’ll use and that you trust. It makes all of the difference in the world.

Lastly, I call on external support. If you need some blogging or writing done, I’m your man. If you need help on taxes or other financial matters, you want anyone but me. So, I pay someone to handle this for me. That way I know it’s being handled by a professional who does the job right.

So there you have it, the three roles every freelancer must play and how I handle them. I hope you found this useful.

About the Author

Dave Caolo is a professional blogger living on Cape Cod, MA. He is an editor at The Unofficial Apple Weblog and is also the web director at the nationally-known museum Plimoth Plantation. Finally, check out Dave’s wonderful personal blog.