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[Guest Post] Sick of the 9-To-5? Here’s What It’s Really Like to Work as a Freelancer

Today’s guest post is brought to you by John Arthur at AND CO, a company that through a combo of smart tech and experienced humans, does the things freelancers hate doing: invoicing, expensing, paperwork and tons more.

Maybe you’re tired of punching a time card, or sitting in a cubicle, or even of your amazing corner office with a view overlooking the Hudson River. Maybe you’re sick of interoffice politics, of your boss, of your commute, or of having to wear pants while you work (ahem, let it be noted, I’m wearing sweatpants as I write this). Anyway, the point is, maybe you’re not cut out for a 9-to-5. Is freelancing a viable option? For many people, the answer is yes.

Working as a freelancer—whether it be writing, editing, graphic design, consulting, or any other endeavor, can be tough, but it can also be incredibly exhilarating and liberating. You can be your own boss. Create your own schedule. Push yourself as hard as you want, or, after hitting all your deadlines, decide to spend the rest of the day lounging by the pool (or hounding new clients).

But Can I Make Enough Money Freelancing?

You will have to consider every aspect of your life, from your cost of living to your work ethic and your talent as a writer/editor/blogger/whatever it is you want to do. But consider the following:

According to, freelance writers can see a wide variety of incomes: “Smart full-time freelance writers and editors annually gross $35,000 and up—sometimes up into the $150,000-200,000 range.” And that doesn’t include the “celebrity writers” who make far more than that. So, can you make enough money freelancing? Yes, there are plenty of people out there making a living by freelancing, and with enough hard work you could be one of them. But it doesn’t happen overnight. Start by building a portfolio, and before taking the leap, save enough money so that you have plenty of back-up funds while you are getting started (and waiting to get paid for assignments). Consider freelancing on the side while you work your full-time job, then transitioning into full-time freelance work once you are ready.

What About The Work/Life Balance of a Freelancer?

The schedule of a freelancer varies. How quickly do you work? How much do you procrastinate? What are your other obligations?

Compare it to more traditional jobs. How much time do you spend at your current 9-to-5 (or is it a 8-to-6, or a 7-to-7)? How much time do you spend commuting? How much time do you spend getting ready for work? How much time do you spend checking your email when you are “off”? Are you ever really off?

As with income, the work/life balance of a freelancer is completely up to the individual. If you’re going to get distracted by episodes of Gilmore Girls on Netflix (wait, what did Lorelai just say? will she ever end up with Luke?) and not get any work done, then maybe you need a boss standing behind your shoulder, and maybe a more traditional workplace is better for you. But if you’re a self-starter who is intrinsically motivated, freelancing might be a great way to develop skills, make a living, and find the right balance of work and leisure (especially if you know when to shut the laptop and put down the phone, or, alternately, when you absolutely need to keep your nose to the grindstone), and even if you feel more comfortable in an office settings as opposed to working from home, there’s always PivotDesk and other options in your area for affordable, convenient office space.

Remember also that freelancing is not just about the projects themselves, but also about the administrative aspects, from creating invoices to finding new clients to keeping track of your work. Fortunately, AND CO can take care of a lot of that for you for a low-to-no cost solution.

Is the Internet the New Frontier?

In the 19th century, we had the Wild West. In the 21st, we have the internet. Freelancers need to be creative with how they reach out to clients, with how they build opportunities, with how they seek new projects. Don’t rely on just one source. Try new things. Be bold. Make pitches to magazines. Make pitches to Fortune 500 companies. What’s the worst thing that happens? No one responds? That’s okay, you’ll be too busy working on the next thing to notice. Saddle up.

What about the Illusion of Job Security…

Maybe you feel comfortable at your 9-to-5, but if it is your only source of income, you’ve got all your eggs in one basket. What happens when your company goes under, or downsizes? You’re out of a job. But what happens to a freelancer who loses a client? If he is well prepared, he already has fifteen others, and a few leads that can quickly replace the work that has been lost. Having multiple streams of income can be safer than having one, because if one dries up, you’ve still got plenty of others flowing in.

What About Health Benefits For Freelancers?

Find someone whose job offers a family plan and marry them, ASAP.

Just kidding, assuming you’re not already covered under a family member’s plan, you can also head to and check out the options that have been made available ever since the passing of the Affordable Healthcare Act. Even if you were working full-time for one organization, you would likely have to pay hefty premiums from your paycheck, or, if your employer was paying for a larger portion, they would likely have offered you a lower salary because of it. Most of it is coming out of your pocket either way.

What Are The Downsides of Full-Time Freelancing?

The downsides of being a full-time freelancer are the same as the benefits. You have freedom to work as you choose, but freedom can be petrifying. You have to motivate yourself to chase leads, to meet deadlines, to develop marketable skills. You get to work for yourself, but that means you will be spending a lot of time with…yourself, and no one else. That also means you don’t have a boss. For every pro, there is a con.

But if you’re the type of person who wants to venture off on their own, who wants to always be learning, who wants to rely only on herself, then freelancing might be a much better alternative to a traditional career. Freelancing, like life, is all about what you make of it.

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