Wanna Do Some Freelance Writing?
In which the author, writing in his pajamas from his home office,
shares tips to make less formidable the task of getting started.

If you work for someone else, you are accustomed to a reliable paycheck regardless of how much work you do in a given week. But those of us who work for ourselves work, in fact, for the clients who come through our door. Sometimes it's a flood and sometimes it's a ghost town. In other words, income for a freelancer is directly tied to effort and circumstance, and therefore is not something one can count on like sunrise.

That, my friends, is the biggest difference between writers with a full-time gig and writers who work freelance.

Freelancing is the stripping out of that cushion of other support people between you and the thousand little challenges of operating a business. As everyone who succeeds at this says, the satisfaction and freedom are immense, but so are the demands. This has been a year for many writers to try it on their own, sometimes by choice and sometimes not. With that in mind, here are six things to consider before you go out on your own as a freelance writer. (And if you're trying it part-time, these are still things you'll want to consider.)

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Figure out if you are ready to live with more responsibility and less certainty. Freelancers live with uncertainty. Some months bring thousands of dollars. Some bring none. Can you live with that tension? The work is not just writing, but running a business: scouring for assignments, dealing with clients, keeping the books (even if you make enough to pay someone to do it, you have to keep your hand in), following up on payment, paying quarterly taxes, tracking receipts… all the things an employer used to do for you are now your responsibility, plus the worry. Are you willing to take that on?

Think about whether you have a physical location to work uninterrupted. Walk through a real day and think about what you physically do. Where you sit and what you do each moment is not a trivial concern that takes care of itself. At the start, you won’t be able to rent an office space or hire an assistant, and maybe not ever. Do you have a place to work undisturbed for long stretches? Will anyone else be in the house? Is it going to be quiet? If you want to leave your desk as it is each night, the kitchen table won’t do—and can you simply work from your laptop and tote a pile of papers in a briefcase without getting frustrated about your nomadic existence?

Know the nut. The nut is the amount of money it takes to live each month without falling short or borrowing, and it includes everything you have to have and are not willing to live without. This will be a longer list than you are thinking, because we spend a lot on things without noticing. This may include cable or subscription TV, coffee runs (which add up crazy fast), gas for your car (though this expense will probably go down if you no longer commute), dining out, plus rent or mortgage, utilities (don’t forget those that bill other-than-monthly), auto insurance, health insurance, retirement contributions (forgot about that, didn't ya?), and of course ransom. (Kidding.) This is how much you have to bring in every month just to get by. Can you do that? Could you do without some things if you had to? Do you have savings already, or a source for a small, occasional loan (which you really want to avoid, by the way)? Does your spouse contribute?

Set up your finances in a formal way. Establish a separate checking and savings account for your writing business. Pay yourself a set amount (the nut plus some extra) each month—do not simply deposit each check into your personal checking account. To know how well you’re doing financially and to minimize worry, you’re going to need some structure. Establish it before you begin, not later, as a desperate response to problems. Create a system to set aside money out of each check to pay taxes. Your employer won’t be withholding anything anymore, so it’s your job to figure out how much to set aside and to send it to the state and federal tax agencies four times a year. Oh, yeah: that Social Security withholding? Turns out your boss used to pay half of it, but now you get to pay it all, which is 15.3 percent on the first $117,000. (Way to incentivize working for yourself, Washington, am I right? #sarcasm)

Network. Don’t be modest. Everyone you meet might know someone who can use your services, but they won’t know to call you unless they know you’re in business. Let everyone know—in person, by email, by social media—that you are seeking clients. Don’t be shy. If you don’t have clients, you won’t have income.

Think about what additional services you can offer the world. I do a lot besides what I started out doing, which was writing speeches. These days most of my work is teaching writing seminars for businesses, associations, and conventions, plus I now have a lot of one-on-one coaching clients. My keynote business is growing as well. But I still write a great deal, and not just speeches. I also write event scripts, books, magazine articles, and op-eds, sometimes for myself and sometimes for others. It is rare for a freelancer to make all their money from just one kind of work. Think about what else you might offer. When you are a writer, your skills are diverse—and it turns out, unique and, therefore, valuable. Use them in creative ways.

Plan your finances, tell your friends, and don't give up.

Freelancing means living with uncertainty. Some people love that, but you might not be one of them. But if you know the challenges going in, you raise the likelihood that you'll succeed.

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Wanna Do Some Freelance Writing? In which the author, writing in his pajamas from his home office, shares tips to make less formidable the task of getting started.

Wanna Do Some Freelance Writing?
In which the author, writing in his pajamas from his home office,
shares tips to make less formidable the task of getting started.