So You Think You Can Freelance? Part 2: Ground Work

Stop! Don’t go any further unless you’ve read So You Think You Can Freelance? Part I: Mindset. If you have (and still want to know more), please proceed …

Photo courtesy of Ryan Swift, Flickr Creative Commons
Photo courtesy of Ryan Swift, Flickr Creative Commons

Welcome to the land of freelancing! I have a feeling you’ll be very happy here.

The bad news: First you’ll have to do all the tax and business license stuff. The good news: You pretty much only have to do it once (or once in a blue moon).

So let’s get the housekeeping out of the way, shall we?

What’s in a name?

First, think of name for your enterprise. Try to keep it general enough that you can expand into other areas without pigeon holing yourself.

You’ll also want to do Google and USPTO trademark searches to pick a business name that’s not already taken and unique enough to register a Web domain, which we’ll get to shortly.

Photo courtesy of Jenn and Tony Bot, Flickr Creative Commons
Photo courtesy of Jenn and Tony Bot, Flickr Creative Commons

Go on record

Once you have a name, you’ll need to register your business by filing a business license application with your state. Get more details here.

I personally recommend registering as an “LLC filing as an S Corp.” It’s generally the best option for (a) the most flexibility and (b) the least paperwork. For instance, you don’t even need to set up a work bank account, if you don’t want to. You can deposit paychecks straight into your personal bank account. It’s pretty headache-free.

Master of your domain

Now you’ll want to register a domain for your business. Even if you’re not doing Web-specific work, it’s still crucial to have a Web presence where potential clients can go to learn more about you.

I used 50Webs to register mine, but there are oodles of others. I know a lot of people use GoDaddy, but frankly, I’ve also heard a lot of negative things about them, too. Do a search online for Web hosting comparisons, like this one.

Mark your territory

To start with, even a basic Web presence is better than none. And by now you’ve registered that domain name, so you might as well put something on it.

I recommend starting with WordPress. It has plenty of free, professional-looking site templates that can be tweaked to look more like a business site and less like a blog. My site is a free WordPress template, for example.

Eventually you might want someone to build you a full site with more flexibility and features, but for now, you can point your domain to this. Plus, then you can put your Web address on your business cards. And people will expect there. If it’s not, they won’t take you as seriously. That’s just the truth.

Life_preserverInsure your peace of mind

This one’s a biggie. If your spouse has a fulltime job, then you can usually share their insurance benefits. If not or you’re solo, then you’ll need to shell out some cash for insurance. There’s no getting around that, and frankly it’s for the best. No one ever plans on emergencies, but they do happen.

The good news is, more and more people are freelancing and thus there are more and more options. Check the Freelancers Union plan and this FAQ on freelancer insurance options.

Make it official

Order business cards. You’d be amazed how far this can go to make you feel legit. And the next time someone asks, “What do you do?” you’ll have physical proof. Most importantly, if you meet someone who could use your services or vice versa, you’ll have official follow-up documentation.

Vista Print is a fine, cheap option for this. (I especially like them for their postcards.) But for a bit more money, Overnight Prints has better quality, in my opinion (and I’ve tried both).

Float like a social butterfly

If any of you follow me on here, Twitter, the MyCastleHeart Facebook page, the Syntax Sorceress Facebook page (my marketing and games writing business), Google+, or LinkedIn, you know that I post daily. Between my freelance business and building an author platform, it’s a necessity these days.

You’ll discover this about the freelance writing space: You have to do a lot of unconventional (unpaid) work to stay top of mind and grab the attention of potential clients. Marketing through social media is an everyday part of life now. Sure, it’s a lot work, but at the end of the day, wouldn’t you rather market yourself and your ideas than something else that you can’t control?


As my talented friend Matt Soell brilliantly put it, working for someone else is:

“… kind of like being a crash-test dummy; you drive a cool care really fast for a few seconds, and then you hit a brick wall, and then someone hauls your shattered self out of the wreckage and puts you in a new car, and the cycle repeats.”

I’ve been there, done that. That’s why I’m not going back. And if you’re willing a to put up with everything I’d told you so far, I’ll let you in on a little secret:

The annoyances of working for yourself pale in comparison to the benefits.

Have any questions? Please ask! I’d be happy to help, or at least point you in the right direction.

Part 1: Mindset
Part 3: Money
Part 4: Q&A

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