Business Advice for the Business-phobe

Freelance writer Ellen Goldstein wrote today’s post. Enjoy!

Some freelancers derive organizational joy from spread sheets, writing down numbers, and following up on unpaid invoices. Others of us would like to just keep writing/editing/designing, thanks, and let the business take care of itself. The problem is, of course, that business never takes care of itself. As a clear member of the second group, I knew I had to change my ways when I went freelance.

  • Embrace the business side of freelancing

You don’t have to love it, but business is like your Great Aunt Matilda, who helped pay for your college education; you owe her at least a peck on the cheek and monthly afternoon teas, listening to her talk about her elderly Pekingese. Just remember what is at stake. If you can’t find a way to deal with your business matters, it’s back to windowless cubicles and two-hour-long meetings about ordering procedures.

  • Go to the places that scare you

Jump right in and do one of the scarier business-related things you have to do. You may find that the anticipation is the worse than the experience, and that making that call to the IRS wasn’t that scary after all. Last week, I finally called an accountant to help me take care of a tax issue that had been plaguing me for a while. It was painful, but it is such a relief to not have this issue hanging over my head any longer. It also frees up my brain to work on the rest of my freelance career.

  • Do one business-related task a day

It doesn’t have to be big. Check up on an unpaid invoice, research CPAs, or even just take a month’s worth of receipts out of your wallet and put them in your deduction folder. Every little bit that you do will help free up time later to do your writing/editing/designing work. Don’t forget to bribe/reward yourself afterward. It works for the toddlers in your life, doesn’t it?

  • Find support

Maybe one of your friends or relatives has experience writing grants or keeping books. Take her out to lunch and pick her brain. Think about hiring a professional, even if you think you can’t afford it. Having a lawyer to write up your contracts shouldn’t keep you from putting food on the table, but it is cheaper than a costly court case. This is the kind of math even business-phobes like myself can do.

  • Enable yourself to be organized

It appears we are all chronically unorganized (this is a great relief to me), because there are scads of books (such as Organizing from the Inside Out, Getting Things Done, and It’s Hard to Make a Difference When You Can’t Find Your Keys) and blogs ( and that can help you create a system and become more organized. There are many different ways of becoming organized and no right way to do it. Probably the most important factor in becoming organized is being honest with yourself about what systems will actually work for you, rather than what you merely would like to be able to work for you. Now is not the time to be idealistic.

After you set up an organizational system, try the piece-of-paper test. If you can’t find a minor piece of paper—whether it’s an unpaid invoice, a bill from last March, or someone’s business card from a networking event last month—in under ten minutes and without dismantling all or part of your workspace, tweak your system until you can.

The Examined Life

After you have been cautiously facing the business side of your freelance career for a couple of weeks, step back, congratulate yourself. Then ask yourself what you still need to learn. Make a list and think about what practical short-term and long-term steps you can make to strengthening yourself in these items. Take a class. Read some books. Call a professional. Ask your friends. Break larger problems down into manageable steps. Make a schedule in order to follow these steps. Think about your strengths as well—it can be as useful to know what you can do right, as to know what you need to work on.

Examine the work you have done. Usually on Fridays, I sit down and tally the number of hours I worked that week and what I did. I also keep track of where I sent my resumes, who I talked to about expanding my editing empire (as I fondly call it), and any formal or informal professional development I have undergone. Weeks and events have a way of slipping by when they are not recorded. The unexamined freelance life is not worth living, because it is too easy for it to slip away.

Ellen Goldstein is a freelance editor and poet living in Beverly, Massachusetts.





7 responses
  1. JR Moreau Avatar

    I loved this blog post. As a young,part-time freelancer, it is hard for me to balance the writing aspect (which I thoroughly enjoy) and the business and money side of it, which gives me slight anxiety (until I actually get paid, which I enjoy as well). With a full time job, it’s tough to get phone calls or emails in related to freelancing business, so to maintain professionalism, I do a lot of this on my lunch break. Making myself more organized has helped me to maximize that lunchtime administrative work.

  2. Lisa Avatar

    OK, Ellen, here’s a challenge for you! HOW do you manage to organize the “stuff” you need and the samples you generate when you’re working (at any given time) on 8 different projects for 8 different clients on 8 different topics?

    I find that I have contracts, in folders, all over the place… because most of my stuff is filed by client, but some clients are one-shot and others are long term… and what’s the point of keeping a contract in paper that you have on disk, anyway?? Or should I save them for a while? If so, where? In a box marked “contracts from random one-shot clients?”

    I have research materials in piles around me, because the amount and type of material I need varies from day/day, week/week. If I put them into boxes or on shelves, they “disappear” on me (under new materials).

    I have samples in a file, but then I have samples that are books (too big) and boxed curricula (way too big). Those are on shelves – but then I forget I have them!

    Re taxes: we hire an accountant and pay the big bucks.



  3. David Dittell Avatar


    Great article; very clear and precise, and it actually made me feel like maybe finances aren’t as hard as I make them out to be. Your piece-of-paper test is a great marker for a working system.


    I don’t know if this helps, but I have a series of boxes in my workspace that I use, one for each project. Sometimes I let things get out of control and there are papers everywhere, but the fact that they have someplace to go makes cleaning up the space less oppressive. (I’m not into regular, boring in/out boxes which don’t have enough space anyway — I use multi-colored milk crates which never seem to get past half full, and I use folders within them to sub-divide.)

    This is different then the boxes I keep tucked away in a closet and almost never open except to put away other stuff. The ones in my workspace are lidless, clearly marked, and right in front of me. Like I said, I still end up with stuff all over the place when work gets hectic, but it’s never completely out of control.

  4. Ed Avatar

    This would have been a wonderful introduction to business methods for writers had it included some concrete examples or suggestions. For instance, what are some often-overlooked tax deductions professional writers can take? Is it better to stay a sole-proprietor or become an LLC? Is an Excel spreadsheet enough, or should a writer invest in something like QuickBooks? What is a list of authoritative sites aimed directly at writers? Maybe a follow-up could be proposed.

  5. Phil Avatar

    Agree with the post. Attention to business side is what separates writing as a business from writing as a hobby.

    Filing can be done electronically, I think the main point is that there be some semblance of order. I usually spend the first hour of the day with this and other organizing chores. Bookkeeping typically goes to the weekend.

    Also, a caveat on hiring accountants: Gain at least a passing understanding of what they’re doing. Some will do things their way, rather than what is best for the business. And though they might have CPA designations (I write for a couple of CPA pubs), they make mistakes, too — H&R Block got its own taxes wrong a couple of years ago. It’s still your name at the bottom of the tax return, so you are ultimately responsible (right on instructions of 1040) if tax filings are in error.

  6. Ellen Avatar

    Thanks for the good words, everyone, and I apologize about my blog manners for not responding earlier!

    @ JR, Keep up the good work!

    @Lisa, I’m with David about boxes. If you have a box for each project you can keep samples and research for each project in one place, and on a “researching dancing panda bears” morning, you can spread out your info for that project and put it away for your “feature article on gardens in New Jersey” afternoon.
    Label, label, label.

    I also suggest having a “one shot client” file box that you keep in the back of your closet. Set up a schedule for going through the box and tossing the ones you think you’ll never need/use again. You can do this once a year? Once every three years? Every time you find the box when you’re trying to find those green shoes you almost never wear? Take a page from food packagers and put a use by date on the box.

  7. Ellen Avatar

    @Ed, Thanks for the suggestions! I’m learning as I’m going along and hope to have a more educated opinion on tax deductions very soon.

    @Phil, Good advice! Do you have any suggestions as to how to make an educated decision when choosing accountants? (I chose mine from a friend’s recommendation.)

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