The Stark Reality of Freelancing

To everyone at the Philadelphia Inquirer and Daily News:

I'm so sorry you've been put in this spot. I can't imagine what it's like to have your paper sold, to fear for your job, and wonder what to do next.

But I can imagine what it's like to ask "I wonder if I could freelance?"

I was there five years ago, and gave it a shot. I learned a lot, and I might be able to share some information to factor into your question, or at least give you an idea of what you need to make a go of it.

I write these not to scare you off, but to show you the stark reality that is freelancing. It's not easy, especially not at the start, and it's not for everyone, either. It can work, but it takes a lot of work.

Here's four things you'll need:

1. You must be an entrepreneur.
Yes, freelance writing is about writing. But 80% of my time is about getting assignments. I don't have a beat. I don't have regular assignments. And I don't have a regular paycheck, whether I write a story or not. As overheard this weekend at the American Society of Journalists and Authors conference, we're like dentists. If we're not filling and drilling, we're not billing. That's a radical change from a staff job, where you get paid based on your skills, not based on how many words you sell.

This is the part that usually pushes people out of freelancing. The uncertainly of work and pay, especially at the tail end of a recession, is maddening.

That's why you need to be an entrepreneur. You need to create a business of one. You need to create your brand. You need to market, and network, and pitch, and follow up. You need to take one idea and spin it six different ways. You need to treat publications like your clients. You need to work on client relations, because without them, you've got nothing.

You're also competing with people who will write for free, or hobbyists who think $5 an article is a great deal. Everyone thinks they can write, but not everyone can do it well. You need to show you're that person who does it well. You'll need to rise above the hobbyists or people who don't value good writing, and then prove to those clients you get who do pay well that you're worth every penny they pay you.

2. You need a cast iron stomach.
I joke that I'm a good freelancer because I'm single and used to rejection. Freelancing is all about rejection, and you need to use it to learn about yourself, and you must get past all the nos to get a yes.

You need to be able to stomach editors, too, who can be clueless, absentminded, and downright mean. You need to be able to hear them say that you suck or you're a terrible writer (I've heard both, and recently). You need to be able to hear them say they won't pay you on time. You need to stand up for yourself, of course, but you need to deal with editors who have what you don't - benefits, a steady paycheck - telling you to work harder for no additional pay. Unless they were once freelancers, they will never understand what your life is like, nor will they care. You need to prepare to do battle with a smile.

3. You must be your boss.
Sounds simple, right? But when it's a nice day out, or you're tired, or you're sick, you must get to your desk and work. Sure, freelancing can mean flexible, but you can be flexible to the point that you put yourself out of work. Go back to number 1. That's why you must be strict with yourself, even be a mean boss, and work.

You have no safety net as a freelancer - no regular pay, no company provided health insurance, no employer sponsored 401k, no sick leave, no vacation, no disability, no union. I'm single and the only person who can pay my bills -- no matter what happens -- is me. This is why you need to be your own boss. You need to work to guarantee the financial security of your company of one.

4. You must be an resilient.
People will not pay you on time. They'll assign something, have you write it, change their minds, and not want to pay you. You'll be told to write for free. You'll be asked to throw in extras for no additional fee. You'll be asked to sign away your rights, to agree that if the client is sued - even if it's because a change your editor put into the article - that you'll take the blame. People will try to walk all over you.

That's why you must be resilient. This business breaks me about once a year. I'll hit rock bottom, say I'll never do it again, and then the roller coaster will come out of the valley and it'll be the best job in the world. But you need the mental toughness to get through those rough patches when an accounts payable person is lying about having mailed a check, an editor demands a rewrite overnight, and two steady clients have folded.

Scared yet? Freelancing can be scary, especially in this financial moment, and in this time when everyone's telling you print is dead.

But it can be done. I've done it, and so have thousands of other writers. The best thing you can do is get the harsh truth first, then find out how to make it work for you if that's what you want to try.

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Phew! OK, so that's my serious post about freelancing. I'm actually thinking of holding a one-day seminar on how to be a freelance writer that would show how it's done. Anyone up for that?