The 4 Top Business Issues For Freelance Writers

by Anne Wayman

Freelance Writer Home OfficeFreelance writing sounds glamorous, particularly if you’re sitting in a cube somewhere wishing you had time to write.  From there it’s easy to overlook some of the very real issues that freelancing bring.

Understanding what you’re facing before you leave your job and doing some planning can make the difference between success and failure.

The top four issues freelance writers deal with are:

  1. Working to your own schedule. When you leave the workforce to freelance you’ll find yourself writing to your own schedule. There’s no official office hours like there were at your job, and while there’s a lot of freedom in that, . When I started I really wanted to just roll over and sleep late, which I allowed myself to do for about a week. I had my first ghostwriting job and I knew I had to get it done. My solution was to make an appointment with myself to get breakfast in a nearby restaurant every week day morning at 9. I wrote there over pancakes and eggs for a couple of months before I could trust myself to get up and go straight to my home office.
  2. Working alone. Several of my writing friends tell me this is a huge issue for them. They find themselves feeling lonely and that loneliness tends to stifle both their creativity and their willingness to continue to work – at least in a home office. Laptops and coffee shops have solved the problem for some. One other is still struggling trying to find the right balance. Some of us, of course, are more comfortable being alone than others. I’m one of those. Knowing yourself is key here and if being by yourself is a problem, figure out in advance your strategy.
  3. Handling the business issues as well as writing. When you’re freelancing you’re in business for yourself. That means everything from benefits to taxes to marketing. You can do these yourself or hire them done, or some combination. For example, I track my own income and expenses but hire a tax professional because trying to sort out IRS instructions makes me crazy. One way or another you’ll need to get all this handled, not all at once, but pretty quickly. Plan for it and you’ll have an easier time of it.

  4. The uncertain income. The nature of freelancing is uncertain income. Even if you’re lucky to land one or two big clients who pay you most of your income, at some point down the road at least one of them is likely to quit working with you. It usually has nothing to do with the quality of your work and the chances are you’ll never know the real reason. It happens to us all. That’s why successful freelancers keep marketing themselves and develop residual income and work toward hefty savings accounts.

Any one of these issues is enough to force some writers back to regular jobs. Most of these potential problems can be somewhat addressed before you make the leap. Another truth, however is, you’ll never know for sure until you try. Do your best planning and don’t burn bridges and you may find you are perfect for real freelancing.

On the other hand, if it turns out working at home isn’t for you there’s no shame in that either.

What’s your biggest freelance issue?

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{ 10 comments… read them below or add one }

Elizabeth West August 11, 2011 at 10:32 pm

Mine is time management. I tend to wait until the last minute to do things that are more difficult, which makes them harder. I’ve been forcing myself to work at lunchtime so I can stay caught up and not have to work all weekend. The goal is to double my output on my content job (which I got from your previous listings, btw :)) and get them all done before the weekend so I have time to work on a languishing novel. I reward myself for working with a round or two of Angry Birds. After I’m finished!
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Website SEO Copywriting - Ron August 1, 2011 at 2:22 am

I would say…the fourth one, Uncertain Income, bothers us all. The next one is the loneliness. If you can manage these two, the rest are just pancakes!
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Brian Clark July 31, 2011 at 2:46 pm

Hi Anne, my biggest issue is all the above. I have recently started researching on-line how to join the freelance community and enter it effectively. Will you help point me in the right direction so that I utilize my time, energy and skills efficiently? FYI, I am a high school teacher with a wife and three young boys ages 4, 3, 1 month old and are planning a fourth child next summer; my goal is to freelance to supplement our income. Any suggestion and/or comments are welcome! THANKS

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Anne August 2, 2011 at 9:26 am

Brian, signing up for the newsletter here is one way to enter part of the freelance world… so is twitter with the hashtag #writers

Buy a copy of writer’s market, both the print and the online version.

And what do you want to write?

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Carolyn Jones July 29, 2011 at 11:22 am

My biggest issue is accountability. I’m new to the freelancing life and am still trying to land decent-paying clients. At this point, I’ve spent more than I’ve earned so it would still be easier to back out and return to the (relative) security of an office job. Luckily, the nanny I’ve hired to care for my daughter is also a freelance writer. I find it invaluable to have someone to whom I can report progress (and frustrations), not to mention the benefits of companionship from someone in a similar situation to me. Perhaps I’d be tempted to slack off if I were on my own. Having someone to whom I’m accountable is an invaluable asset in the writing trade.

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Anne July 29, 2011 at 11:35 am

Yes, that’s one reason I value my mastermind group and my accountability partners so mcuh.

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Nina Lewis July 28, 2011 at 3:35 pm

Mine is part of the marketing issue: finding clients that pay well.

The other part is attitudinal: I feel I’m not ‘good enough’ or experienced enough for some freelancing opportunities that I see on job boards.

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Anne July 29, 2011 at 11:41 am

Yes, until you recognize you’re good enough you’ll have trouble finding clients that pay well.

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Benjamin Hunting July 28, 2011 at 3:23 pm

Very good advice, Anne.
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Anne July 29, 2011 at 11:50 am

Thanks Benjamin.

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