Ready to Freelance?

In which the author, writing in his pajamas from his home office, shares tips to make less formidable the task of getting started in an independent endeavor.

NOTE FROM MIKE: Thinking of freelancing? I maintain a small cohort of one-on-one advising clients, a maximum of three in any month. I can help you decide if freelancing is right for you just now, plus provide support for all aspects of your new operation including business set-up, marketing, and pricing. Available in 30- and 60-minute sessions or monthly. Wanna know more? Email me.

The most difficult part of freelancing comes in the first few months, when you realize that income no longer arrives through a constant channel, in a specific amount, at a regular time.

Never will the connection between money and effort be clearer than when every dollar you see is associated in your busy brain with the efforts at your desk.

It’s a bracing introduction to the real world.

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. That's why I am sharing six things to do before you start freelancing:

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Figure out if you are ready. 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 practicalities. You won’t be able to rent an office space or hire a comely assistant—not now, maybe not ever. Do you have a place to work undisturbed during the day? 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? 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.

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 incidentally, without thought. 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)

Prepare to 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. You don’t have to advertise in a formal way, but you do need to let everyone know—in person, by email, by social media—that you are seeking clients. Don’t be shy about it, either. Plus, you don't have a choice. If you don’t have clients, you won’t have income.

Think about what else you can do. You can tell from the variety of things I write about here that I do a lot besides what I started out doing, which was writing speeches. I also write event scripts, I ghostwrite books, I contribute to magazines, I write op-eds, I do some PR consulting, I teach and design curriculum at Georgetown, I do corporate lectures, and I even occasionally tutor working professionals. It is rare that you will make all your 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.

Freelancing requires planning, patience, and persistence.

Freelancing is about living with uncertainty. Some people love that, but you might not be one of them.

Freelancing may not be for you, and that’s fine. But it’s better to know before you begin than to find out after you’ve been scared and broke for three months.

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