Be Your Own Big, Mean Boss (With the Help of Shareware)

By Allison Ruffing

My first actual day as a full-time freelance writer, I went out to lunch, then went home and watched three movies in a row. Including Weekend at Bernie’s.

Clearly, I was procrastinating hard-core.

I couldn’t believe I was being so lazy. If I’m such a Type-A nutcase, why isn’t my novel getting done?

Simple answer: I was my own boss. But I was letting my employee – uh, also me – call the shots.

I was going to have to put on my boss hat and get tough on this slacker who had taken over my home office. Once I did, I started writing daily and working on a ton of other freelance projects, too.

Here’s my three-step plan for getting in touch with your inner big, mean boss:

1. Install A Time Clock. That’s right – punch in, punch out. If you Google “timesheet software” you’ll find a ton of free or pretty-close-to-free options. I installed an awesome program called HourGuard that actually lets you punch a button when you start a project, punch another when you’re done, and with one click generate a report for each day, each week, the whole year, whatever.

Whether you track your time with a program, or just jot down stop and start times on a pad of paper, you’ll find you’re much more likely to stick with a task when you are holding yourself accountable in some way. At the end of the day, you can review exactly how you’ve spent your time, instead of getting to 5 p.m. and thinking, “Gosh, that Facebook just eats the day up, doesn’t it?”

Bonus tip: Include yourself in your client list, so you’re forced to make time for all the personal professional projects you’re working on—that book you’re writing, that Web site you’ve been meaning to launch, researching new markets for your work.

2. Make A To-Do List. Sounds trite and obvious (not to mention unpleasant), but the truth is, if you don’t write everything down, you’re going to forget stuff, which then leads to panic, which then leads to subpar work.

I’m of the Getting Things Done school of thought—write it down, or type it in, so you don’t have to waste energy remembering it. It’s hard to be creative with your fiction characters when you’re trying to remember milk, eggs, toilet paper, and postage stamps for your next Walmart trip.

I installed a nice little to-do list shareware program (Easy To-Do) and put everything, everything I had to remember into it. Now when a task is complete, I get the joy of putting a check mark in that little box. Highly satisfying.

3. Slim Down. The size of your to-do list items, that is. One day as I was staring at my computer screen, in full-on procrastination mode, I realized: “Write novel” was actually on my to-do list. One task. A task of equal weight with “defrost something for dinner” and “reschedule hair appointment.” But you can’t write a novel in one day.

I knew, of course, that there was no way I could put a check mark in that box by 5 p.m. And that, ultimately, was what was keeping me flying through my Netflix queue instead of my fiction. Not writer’s block. Just the knowledge that this book project was so massive, so many thousands of words, that there was no way I could finish today. So instead of getting started, I stalled. Instead of doing a little, I did nothing.

When you’re feeling overwhelmed by gi-normous projects and procrastination sets in, put on that boss hat again and help your employee manage that workload. Break projects down into reasonable steps, and make each of those steps an item on the to-do list. Make the steps small and so manageable that it would be nearly impossible not to complete at least one each day. In my case, I deleted “Write novel” and replaced it with novel-writing steps like research setting details. Set up Word doc format. Brainstorm titles. Outline plot. And finally, write first few paragraphs. (That was a tough day, but I used my break-it-down technique and focused on one paragraph at a time.)

Now that I am into the actual writing of this novel, I have simplified the process even more, setting up a recurring task in my to-do list that says, oh-so-simply, “Add to novel.” Could be a paragraph, could be a page, could be an entire chapter on days when I’m really feeling it. As long as I add words, I get to check that thing off. And it feels good. The novel is slowly taking shape, and up to 33,000 words now.

So…that’s how I turned an unstructured, unproductive home office setting into a well-oiled productivity machine. I still take the occasional two-hour lunch, though. My boss is pretty cool about stuff like that.

About the Author: Allison Ruffing, a freelance writer and media consultant who lives in Northwest Indiana, loves two things—writing and the Internet. She’s currently hard at work on her first novel, as well as many Web and social-networking projects. If you enjoy the humorous side of technology (or you’re, well, still looking for that humorous side), check out her blog at, or follow her on Twitter.

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