It’s been four months since I quit my job, but I’ve reached the point where I’m able to pay my bills with just my freelance gigs. I think that finally qualifies me as a professional freelance writer.

I decided to become a freelancer for pretty typical reasons. I wanted to be my own boss. I wanted to build my own schedule. I wanted to work in my pajamas and never sit through another boring meeting again. I wanted to flex my writing muscles by writing for a variety of places including a tech blog, a women’s career advice blog, and even a print magazine.

That’s basically what my life has become over the last few months, and it’s awesome. But—and you knew this was coming—it’s not ALL awesome. There’s a lot of work associated with freelancing that I kind of skimmed over when choosing this career path. Here’s what I’ve learned only by doing:

It doesn’t happen overnight

In the state of Virginia, where I live, you don’t become self-employed by filling out a form or acquiring a license. You simply start working and voila: you’re a sole proprietorship.

The trick is coming by that work in the first place.

In December, I wrote a list of 30 media outlets where I’d love to see my byline. But when I pitched all of them and didn’t hear back from most, I started to get discouraged. It was only when I started leveraging my connections—with colleagues from previous reporting jobs, writing mentors, and LinkedIn—that I started getting promising responses.

Really, I should have known this already. When I set out to apply to 30 jobs in 30 days in 2010, I heard back from 40 percent of companies where I had a recommendation from an employee.

It takes forever to get paid

By February, I was working for three different publications. However, I only made $300 that entire month. What happened?

It wasn’t that I’d only done $300 worth of work. It was that I was invoicing—AKA requesting to be paid for my work—in a way that was slowing down the process. I was waiting to charge for my work until stories were published, which could be weeks after I’d written them. Soon I got smart and learned to invoice as soon as I’d completed my part of the bargain.

Now, I’m on retainer for a few different places, which means I don’t have to invoice every time I write an article. I either invoice just once a month, or they direct deposit. It’s closer to what it feels like when you have a regular paycheck.

Your taxes are the length and time commitment of a short novel

How did you spend last Friday night? In my case, my supportive fiancé and I watched video tutorials on the IRS website. Starting this June, I begin paying my taxes four times a year, a process that’s called paying estimated taxes.

Why pay estimated taxes? As a freelancer, my employers don’t withhold any of my income like they would if I were full time. I’m also unsure how much income I’m going to earn this year. So instead of guessing wrong and ending up owing $10,000 to the IRS next April, I’m paying as I go.

Self employed people are at an elevated risk of getting audited, since the IRS claims most tax fraud occurs within the ranks of self employed people. If you ask me, I’d wager that many self employed people just don’t understand how the tax code works. For example, I have to fill out the deceivingly similarly named forms 1040 ES and 1040 SE. And that’s just the beginning!

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All in all, I never realized how similar freelancing is to entrepreneurship. You have to be your own publicity agent and your own financial bookkeeper. I don’t spend more time writing than I used to, but I do spend more time working—on these related tasks. It’s hard, but energizing to realize that I’m better at math and administration than I thought.

This isn’t a rags to riches story. I’m not more financially successful than I used to be. (If anything, things are about the same.) But I feel like a more fully realized person now for proving to myself that I can do this.

Would you ever consider a career as a freelancer? Why or why not?

(Photo by Philip Taylor.)

Take a look at the much-neglected LaurenRaeOrsini.com today, and you’ll find it completely transformed. It’s been reskinned with a brand new custom theme, Writer’s Blocks, built from the ground up by my friend and designer, Sean Connolly.

I love WordPress to death but one thing it’s lacking is a variety of portfolio themes for writers. You can find tons of portfolio themes if you’re a visual artist or graphic designer, but if you want to show off words instead of pictures, you’re out of luck. I knew that if I wanted a theme that did what I needed, I’d need something custom, something that added to and altered WordPress’s out-of-the-box functionality. Sean helped me do that, and I’m encouraging him to make Writer’s Blocks Theme available to the public soon.

Some of the features of my new portfolio site:

• No posts, and therefore no comment spam. Sean added a new content type, Clips, which I can edit visually from the WordPress Dashboard.
• A 3×3 grid of my portfolio clips referenced by either title, quotation, or photo. I love the variety this adds to the main page.
• Responsive design. Try dragging the corner of the site and shrinking it. Whether you’re on a big screen, small screen, tablet or phone, it looks good!

I invested a lot of thought, time, and money into making my portfolio something I could be proud of. I think my reporting clips make or break my ability to get new reporting jobs, so I wanted them to be accessible, readable, and well-organized.

Do you have a portfolio site to showcase your work? Link it in the comments!

I was going to call this post, “My office essentials,” but one of the best parts about my life is that I don’t have an office. Sometimes I work with my scaly coworker Fintan at the minidesk above. Other times I sit on the couch. In summer, I walk to my closest library branch, which is in the middle of a community park. In winter, I drive to the larger regional library.

No matter where I am, there are a few essential tools I can always rely on, all of which are easily portable to any workspace. Here they are, in order from priciest to free:

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15 inch Macbook Pro: I picked the biggest screen available because sometimes it’s my entire world for the duration of the work day. If I could commit to working from a single desktop all the time, I’d definitely be one of those people with two screens.

My parents bought me my first Apple computer as a college graduation present so I could use it for journalism school. Four years later, it’s really time to replace it (since its battery life is only about 20 minutes), but I realize that it isn’t a very affordable option. So for my next computer I’m thinking about getting a refurbished Macbook or a much cheaper PC ultrabook.

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Adobe Creative Suite: At about $1200, this isn’t any more affordable, but I got it for free. As an adjunct professor for American University, I got the Student and Teacher edition installed on my personal computer so I could use it as a teaching tool. If you’re a student or teacher, you might be able to get a free version, too.

I am currently using Adobe CS5, but CS6 is the latest available. I use Adobe InDesign to format my digital guides. I use Illustrator to create web design wireframes, infographics, and any graphics I use on this or other sites. I use Photoshop to alter and edit pictures I take. Dreamweaver is the only one I use in my teaching curriculum.

There are ways to make this a little more affordable, by looking for the nonprofessional versions of each program, and by only buying the ones you need. For example, I use Adobe Premiere CS5 to edit my vlogs, but I could easily use Adobe Premiere Elements 11, the amateur and far cheaper version of the same program.

But if you’re honing your skills for a design or Web design job, I’d find a way to get my hands on the commercial version. These are required skills for most design jobs, at least the ones that I’ve applied for.

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Nikon P7000: I don’t know much about cameras, so I didn’t buy this online. I went to Penn Camera, a local chain in DC, and let an employee walk me through all the varieties. This one was described to me as “what professional photographers use on weekends” and I liked that. Video and audio wise, it has a mic jack in case I want to record on-screen interviews, and it shoots in widescreen.

When it comes to still photography, I’m still learning. My New Year’s resolution was to keep my camera on its manual setting all year long and learn how to adjust the aperture and shutter speed. It’s a lot more interesting to take photos this way.

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Benro aluminum tripod: This is what I use when I’m recording my vlogs, plus any other time I take video. I bought this when I was doing a lot more documentary work for school so the $200 price was more worth paying then. This is the most lightweight tripod I have ever lifted, perfect for people with smaller frames. I wouldn’t think anything of carrying this around on my back at an anime convention, something I have easily done before.

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Reporter notebooks: This is the same brand I’ve been using ever since I began my first journalism internship at the Free Lance-Star. They’re simple, iconic, and you can buy them in bulk. I look like I’m 12, but nobody second guesses my authority as a reporter when I’m holding one of these. I use them when I’m reporting in person as well as when I’m just recording timestamps for a phone interview.

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Pilot Precise V5: The only pen I use. It’s got a thick point (compared to the smaller V7 option) that will bleed through thin paper. I like knowing that my writing isn’t going to fade away. Also, they come in every color (but I still only ever use black).

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Garageband: If you have a Mac, this is free. If you have a PC, there are a lot of similar, free programs. I use it for phone interviews. If my source allows, I put him or her on speakerphone and start Garageband as if I were recording a podcast. Then I take notes on paper to mark the timestamps for significant quotes. It’s significantly improved my accuracy.

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Record my Call: Another alternate to Garageband. This Android app is a one-touch recording program. However, you still need to have the subject on speakerphone for it to sound good.

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Google Drive: Just in case you’re living under a rock, here’s why you should use this free, cloud-based, sleek Microsoft Word clone. You’ll never lose a document again. If your computer shuts down, Drive’s automatic saves keep your file from disappearing. You can also work on a file at home and then open it up to print it somewhere else. No more zip drives.

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tomatoi.st: As I talked about in my first vlog, this Pomodoro Technique tracker has changed my entire writing regimen. If your brain works best in sprints like mine, this tool forces you to focus for just 25 minutes at a time before taking a break. It also cuts down on procrastination because you can tell yourself, “I’m just going to work for a quarter of an hour and then relax.” Usually you’ll end up wanting to work for far longer than that!

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Do you have a nomadic workspace? What tools do you consider your essentials?