Help me impose structure.
April 29, 2011 2:44 PM   Subscribe

Desperately disorganized person seeks realistic routine.

I have been working the last 18 months as a 1099-er. I've had as many as four jobs at once for writing and editing clients. I'm also an adjunct at the local state school, with a busy course load during the semester (which is just about over).

When all the work started getting to be too much to keep in my head or in my normal note taking system (fill up a piece of legal paper with overlapping notes written in all directions on multiple topics) I got a smartphone. It's a fun toy, yes, but it also seriously helped me take a giant step toward being productive and organized. One big issue was forgetting about an appointment or phone call, double-booking, and having to ask someone to change at the last minute. The results of using Google calendar have been amazing. Good first step.

Now, my main problem is scheduling my work days. I can arrange my days however I want to, and there's the problem. I wake up in the morning without a plan, and by the time I have noodled around, seemingly randomly, with several different projects, it's lunch time. That's not to say I'm totally unproductive, but there are days when I am totally unproductive (like today!)

So -- this question is especially for freelancers, especially for freelance writers and editors, esp. for freelance writers and editors who have conquered their natural (or deep-seated) tendencies to be completely disorganized -- what has worked for you?
posted by Buffaload to Work & Money (6 answers total) 44 users marked this as a favorite
I have friends in the same situation that swear by The Pomodoro Technique.
posted by mikesch at 2:46 PM on April 29, 2011 [1 favorite]

Best answer: I freelanced for two years. You definitely have to learn organizational skills and self-discipline to succeed at it. But they are learnable.

Keep to-do lists—this is as huge as keeping a calendar. I use Zenbe Lists, which is free, and (like Google Calendar) can be accessed from both a desktop Web browser and my iPhone (and will automatically sync between the two). I keep general lists, lists for specific projects, and sometimes even finer-grained lists for specific sections of projects. That way, I always know what remains to be done on a project—and when I find myself wondering what to do next, I can just glance at my lists, and pick the item that I can make the most progress on at that moment.

Whatever your work days are, stick to them. I found Monday through Friday to work best, just because that's the schedule the rest of the world follows—my clients and partners weren't available on weekends, and my friends weren't available on weekdays.

Wake up at the same (early) time every day. Hop into the shower, eat a quick breakfast, and get straight to work. Don't tell yourself you'll do the work later in the day, or try to get other stuff done (even productive stuff, like housecleaning) until your work work is done.

How do you know when your work is done for the day? Figure out how many billable hours you need to clear each week to cover your expenses and make a reasonable profit. Divide that by five workdays. That's how many billable hours you need to do each day. For me, it came out to 5–6 billable hours a day. (This will also discourage you from wasting time on fun-but-unprofitable things.)

But seriously. Get up at the same time every day, and get cracking first thing. It's a great feeling to break for lunch and know that you've already gotten a ton of productive stuff done.

Sitting down and getting started is the hardest part. If you have trouble getting started, just tell yourself that you can quit after ten minutes if you really don't want to keep going. It's a lot easier to keep going after ten minutes.

If you work from home, get out whenever and however you can. Take your laptop to the coffee shop, and do billing and email from there. It'll keep you sane.

Do take days off, even when you feel swamped. You won't be doing yourself any favors by burning out. In the long run, you'll get more done if you regularly take time to recharge and relax.

What do you use for billing and bookkeeping? I used the free version of Quickbooks for a while. It was adequate, but I had to use a separate tool to keep track of my time, and I got sick of reconciling the two. So I checked out five or six Web-based tools, and settled on FreshBooks. It does bookkeeping, time tracking, invoicing, and more, all in one place. Clients can log in, view and pay their outstanding invoices, and receive automatic email notifications. It's totally affordable and easy to use. QuickBooks felt more like something I had to do; FreshBooks felt like an assistant that was actually helping me be more productive.

When you're juggling multiple projects, it's time to prioritize.

Deadlines aside, the highest-priority task is the one that will put the ball back in a client's court. (There are always revisions and additional requests, right?) Let's say you have 12 hours of work to do on BigProject, and 4 hours of work on LittleProject, before you can give them to the respective clients for review. You can spend the next eight hours in one of two ways:

1. Work on BigProject, and leave LittleProject on the back burner for the moment. At the end of the day, both clients are still waiting on you. You could finish both projects tomorrow, but then you'd be sitting around twiddling your thumbs while you wait for feedback.

2. Get LittleProject turned around to the client, and then put in 4 hours on BigProject. While you're working on BigProject, the client can review LittleProject, and thus LittleProject is moving forward instead of standing still. By the time they get back to you, you'll have put a solid dent in BigProject, and maybe even turned it around to its client—so it can keep moving forward while you do the revisions to LittleProject.

Basically, I found that the smallest and easiest task was often the best one to work on, logistically speaking. (This breaks down in the face of truly piddly nickel-and-dime stuff. But you don't want those jobs anyway.)

When things got really busy for me, I found it helpful to print out calendar pages for the month, and draw differently colored bars for different (often overlapping) projects. This helped me keep track of deadlines, avoid overloading myself with work, schedule new work, and set realistic client expectations ("well, let's see—I'm booked up at the moment, but I'm expecting things to clear up mid-week next week. If you can get me the materials by then, I can probably get it turned around by the 23rd").
posted by ixohoxi at 4:06 PM on April 29, 2011 [35 favorites]

I've never finished the whole book but reading the first few chapters of Getting Things Done has been really helpful for me. There's a lot of online fandom and commentary about it which can be really helpful too.

Also, 3x5 index cards with a binder clip in your back pocket is pretty awesome for grabbing thoughts. The more you use them, the more you get out of them.
posted by sully75 at 8:51 PM on April 29, 2011

You might also take a look at David Allen's Ready for Anything, which I personally like better as an intro to GTD than GTD the book.
posted by jgirl at 6:49 AM on May 1, 2011

Response by poster: This is great stuff -- still open to more suggestions. Appreciate your input as always, guys.
posted by Buffaload at 3:50 PM on May 2, 2011

Also take a look at Streamlining Your Life by Stephanie Culp. It's very concise and no-nonsense. I used to make a point of reading it every few months, but my library seems to have taken it out of circulation. I need to get a copy, and I cannot recommend it highly enough.
posted by jgirl at 8:56 AM on May 7, 2011

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