By Tim Hillegonds.

The freelance daydream has been permeating the minds of closet word nerds in corporate America since the invention of the cubicle.

It’s my theory that the first person to be locked inside the three-sided Eradicator of Creativity immediately sat down and started typing query letters—the literary equivalent of digging an escape tunnel with a spoon. There’s just something about vanilla colored walls, industrial carpeting, and annual “Biggest Loser” competitions that has a certain group of us questioning the meaning of our lives.

From inside the cubicle, freelancing looks a lot like Canaan—the land of milk and honey and setting your own schedule. And although there are parts of freelancing that are indeed akin to the promise land, it’s not all manna and miracles. In fact, if the jump from corporate America’s private jet isn’t thought through, the landing can be pretty darn violent.

But, as I’ve learned over the course of the last six months, it doesn’t have to be. And since clichés around taking chances are abundant—and leaving the corporate world to freelance is akin to skydiving—here are three things to think about when taking the ultimate plunge.

1. Check your equipment

I spent ten years in the insurance industry. That’s ten years of making connections, writing emails, saving phone numbers, going to conventions, and putting up those stupid folding booths at trade shows. And while most of the people I met I’ll probably never talk to again, there are a select few people that I stay in touch with.

Prior to leaving the cushy job, take a look around and ask yourself a few of these questions.

• Who can help you once you leave? Mention your plan to a few close colleagues and do everything you can to exploit every connection you have. Assignments can come from anywhere, even the places you’d least expect. You’re last job before you leave is to prime the pump and make it a little easier to land that elusive first job.
• What other businesses do you work with that are potential markets for your writing? In my case, the insurance industry is filled with brokers, appraisers, reinsurance markets, accounting firms, industry periodicals, and a vast array of other businesses and associations. Each one of these is a potential client or market. I’ve got insider industry knowledge that the average writer might not have. Plus, certain people at these companies know me, which means I’m sitting on warm leads, rather than shivering my rear end off on cold ones.
• Can you sweet-talk your media relations (or marketing) specialist into allowing you to write copy once you’ve left? It might seem like a tough sell, but most corporate marketing departments are one-size-fits-all operations. Just because someone holds a position in the marketing department doesn’t mean they know how to write compelling copy. (This is especially true in the insurance industry.) Before you leave, show them what you can do by rewriting a product description or sales one sheet. There’s nothing better than leaving a job and still finding a way to have them pay you.

2. Jump and free-fall

Once you’ve actually made the jump, the fun begins, right? Well, not always. Most people find that freefalling is tough. The structure that you’ve become accustomed to is suddenly gone. You’re now totally self-reliant. Oh, and that nice paycheck you used to get every other Friday? Yeah, that’s gone, too.

Some people panic, but I can assure you, panicking doesn’t help. So, what do you do? Simple: You organize. Remember all those connections you primed right before you left? Now’s the time to start contacting them. Here are a couple other things to consider, as well.

• Block out your time. That old saying about idle hands being the devil’s playthings is spot on. You need keep them moving. Set aside time in the morning to reach your connections. Make phone calls. Write emails. Get your website set up. Fill your calendar with tasks. The more time you spend working towards your goal of landing clients, the less time you’ll have to panic. Of course, you reap what you sow, too. And in the beginning, it’s a numbers game.
• Apply the lessons of corporate America. If you worked for a publicly traded company, chances are you worked in a highly regulated, process driven organization. Perhaps you even worked at a “management by objective” company. Since you’ve now essentially turned yourself into a walking, talking small business, it’s time to look at the processes you used to employ and see which ones you can apply to your newfound purpose. And remember, billion dollar companies didn’t become billion dollar companies by winging it. Successful freelancers don’t become successful by winging it either. They leverage their existing knowledge.

3. Pull the chute, then tuck and roll

As a guy who’s actually skydived, I can tell you that there are two things that happen after you pull the ripcord. First, the impossibly loud sound of the wind whipping past your ears at 120mph is replaced with an eerie silence. All the chaos that you’ve been going through for the last minute or so disappears and you feel wonderfully at peace. (Sound familiar?) Second, you get ready for landing, which may or may not be bumpy.

When you make the giant freelance jump, chances are the landing is going to be rough, so you’re best bet is to get ready to tuck and roll. Prepare yourself for the days ahead as best you can, but know that once you’re out of that corporate jet, there’s no going back. But that’s a good thing. And it’s also something you can use to your advantage.

America—even corporate America—loves an underdog; so don’t be afraid to play that card when trying to land new clients. When you talk to your old colleagues, play it up. Tell them you left to chase your passion. Tell them you couldn’t handle not being true to yourself for one second longer. And then ask them to help you. As elementary as this may sound, it’s imperative that you ask.

When you make a choice to follow your dreams, people respect that. Heck, most of them with they could do it, too. And some of them will even reward you with assignments for it.

Not everybody loves to skydive, but we all like talking to people who have. Perhaps it’s because they’ve experienced something we haven’t. Perhaps its because they survived. But that’s the thing about making leaps. We can survive.

It’s actually jumping out of the plane that’s the hard part.

Tim Hillegonds is a Chicago based-freelance writer who spends most of his time boxing, playing soccer, and trying to convince his wife that the terms freelancer and unemployed are not synonyms. He’s got a blog, a book, and pit bull named Uriah. You can check out his site at www.timhillegonds.com.

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