December 06, 2012 0 Reactions

Your ‘Independent Moment’ — When to Make the Leap to Freelance

By , under Make it Work. James O'Brien's work can be found at Mashable, OPEN Forum, TheAtlantic.com, and elsewhere. He writes about media, business, and tech.

A question for independent writers in the making: Are you waiting for some sign in the sky? Just when are you going to make your leap?

If you’ve been waiting for your independent moment — moving from traditional full-time employment to supporting yourself via independent/freelance writing – maybe the time is actually now.

The knowing is the battle, isn’t it? How can you possibly be certain that you’ve got the skills, the portfolio, and the potential client base to make the shift — and skirt the wide-open pit of disaster that seems to loom at center of the stretch?

Well, here’s the bad news. This article cannot solve that problem for you, and in many cases, you’ll never know for certain. But here’s the good news: Many independent writers have figured out how to make their own leaps. You can, too.

Evaluating the Independent Moment

You’re working hard, writing what and when you can, and wishing you could start somewhere — make a business of your words from the ground up. And then there’s a moment when a window opens onto that reality.

There are some indicators to look for, but they vary from person to person, from moment to moment. Picking out some of the commonalities, though, here are three models:

1. Side-work to Main Gig

Take the example of Khaleelah Jones, who now runs a successful self-employed copywriting office in London. Her independent moment wasn’t an overnight transformation but a stepping-stone process.

“I was lucky in that I was able to take a ‘test run’,” says Jones. “I started freelancing on the side as a way to generate extra income, then took the leap when I left my job to go back to school for a master’s degree.”

Granted, this kind of doubling-up on the workload — think of it as a Venn diagram in which you nudge the overlap further and further toward independence — is going to mean (a lot) more work in the short term.

But it’s also going to mean that you can measure the rightness of your independent moment by the bottom line: sufficient cash flow. When you’re making enough to support rent and utilities from freelance work, you’re ready to grab that opportunity.

2. The Unexpected Subsidy

Traditional work can play a role in recognizing the independent moment in another way as well. If you worked as a writer, particularly as a journalist, in the latter half of the 2000s you may have encountered just this impact.

It’s called a layoff.

The hidden advantage of the unexpectedly out of work writer is the subsequent appearance of an unexpected subsidy.

Unemployment benefits. Likely to be just about one-third of your usual take-home, that’s a few hundred bucks a week.

Add one or two small assignments to the mix and you’re working the Venn diagram again. It’s just that the clock is ticking, now, whereas in the preceding model it is not.

And note that this model is, at the start, almost entirely reliant upon a multi-income household. Could be roommates splitting costs, could be that your spouse has got your back, but you’re probably going to need somebody on your side.

(On a personal note, this is precisely how I made my leap, in 2008. With months of checks in front of me, and my freelancing client-base only large enough for part-time work anyway, I saw the chance to help support my household and still grow my profile and income. Seventy-hour weeks, to be sure, but when I came out of the chute I was fully fledged and indie — still am.

Be aware that there are limits to how much you can earn before a state will shut off the unemployment-insurance spigot, and be sure to talk to an accountant about how to handle unemployment benefits and taxes.)

3. The Crucible Model

Imagine being an independent writer and not even knowing it. This is a large part of the story of Mridu Khullar Relph, of New Delhi, India, starting in 2004.

“On Christmas Eve, I was broke.” says Relph. “Utterly, completely broke.”

She was out one missing check from her full-time employer, and she had no freelance checks incoming (Relph was already working on model no. 1, you see). No word from her boss over the holidays. No money to spend.

“And then, just like in the movies, something absolutely amazing happened,” she says. “On Christmas morning, when I opened up my computer to check my e-mail — okay, bank balance — there it was. An e-mail from an editor at a top national magazine, who was interested in an idea I had pitched. Here I was, dead broke, wondering where the next paycheck would come from, and there I was, halfway to a $1-per-word assignment.”

Every writer probably dreams of a moment such as this one. For Relph, it prompted her to think very seriously about where her career was going. All the elements — full-time work, freelancing, the future — ended up in that crucible.

When the check from the full-time gig finally arrived on Jan. 2, Relph ran her numbers. Turns out she’d already been making more at part-time freelancing than at traditional gig, anyway. Her independent moment was upon her. It simply took the sudden wake-up call for her to realize it.

Lesson: run your numbers often!

“I have now officially quit my job and am a full-time writer,” Relph says. “The bills are taken care of, the loans mostly paid off, and queries are flying all over the place. Life is good. That e-mail on Christmas morning is a gift I won’t forget. It got me started on my journey as a full-time freelancer.”

The Back and Forth of the Moment

Finally, it doesn’t have to work out perfectly, the first time.

The independent moment is a make or break deal, but in most cases it’s not a one-time deal. If you take your stab at it, but end up back in traditional full-time work, that probably just means that this independent moment eluded you.

That’s the story of Kathryn Hough, of Portland, Ore. She started out as a part-time freelancer writing copy, went full-time, then decided that the freelance life was the better of the two (she also recently started a company with her husband, in 2012). Money often drives these fallback motivations.

“I did have a few hiccups,” Hough says. “I thought that all clients would pay on time, and they never do! I over drafted my checking account twice before I had saved enough to cover the gap. Now, I have many clients, and my income is higher.”

In my experience, I leveraged the unexpected subsidy moment, but then backtracked briefly to a traditional-employment editing job — because of money.  I was worried about what would happen when the first assignments ended.  Later, I realized that I needed to get back to the independent opportunity before it slipped away.

This may happen to you. It’s normal. Think about the models, look for the indicators that suggest a second, third, fourth (whatever) chance to go full-time independent, and keep writing.

Images courtesy of Igor Petrov/shutterstockLo-Random/shutterstock

 

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