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The Realities of Freelancing—How to Know if it’s Right for You

By Kat Boogaard

When I was going through the torturous process of trying to decide whether or not I should quit my cushy, safe, and predictable full-time marketing job in favor of pursuing a career as a freelance writer, I had big dreams for myself. Big dreams.

Yes, I’d sit there in my stuffy cubicle—my head filled with visions of what my life would be like once I took that freelance leap. Sitting at the corner table in a quaint coffee shop working on my next great piece of work. Staying in my pajamas until 3PM. Not having a boss to report to.

So, when I finally did jump ship from my full-time gig and transitioned into life as a freelancer, let’s just say that I was, well… surprised.

Why? Well, there’s a lot that goes into freelancing—I placed emphasis on a lot for good reason. It’s easy to get wrapped up in all of the things there are to love about freelancing. And, trust me, there are a lot of those.

But, that doesn’t change the fact that freelancing probably won’t fulfill all of your daydreaming fantasies—at least not without bringing a hefty dose of reality along for the ride.

The Realities of Freelancing

Freelancing and contract work has been growing in popularity for years. In fact, a lot of research estimates that 50% of the U.S. workforce will be freelancers by the year 2020. And, while being a freelancer undoubtedly comes with its fair share of perks and upsides, that doesn’t mean it’s always easy.

Many prospective freelancers fail to think about the practical challenges that come along with making a living completely on your own. You need to pay your own taxes and fund your own retirement plan. You need to find health insurance. You need to manage the accounting and administrative duties yourself, or hire someone to do them for you.

And, that’s all unbillable time—you need to do all of that while also completing high-quality client work that will actually pay your bills.

So, now that we have that brutal dose of reality out of the way, you’re likely wondering how you can determine whether or not freelancing is the best choice for your career. Ask yourself the following five questions to start to get some clarity.

1. How well do you manage your own time and workload?

“It must be so nice to be your own boss!” is something you’ll hear echoed time and time again when you’re a freelancer. And, yes, not having a boss breathing down your neck or micromanaging your every move can be nice.

However, if you’re not a self-starter who can give yourself the kick in the pants you often need in order to get things done, freelancing will be a challenge for you. Some of us need that accountability in order to stay focused and be productive.

So, if you don’t think you’ll be able to adequately manage your own time and workload, you might want to consider sticking in a more traditional employment situation with a more rigid structure.

2. How organized are you?

Freelancing involves some serious organization skills, regardless of your chosen field. You need to keep track of everything from your receipts, expenses, and invoices to your urgent emails and knowing when it’s time to buy some more highlighters.

Of course, if organization hasn’t been your thing up to this point, those are definitely skills you can refine. But, if you can’t see yourself ever staying on top of all of the moving parts involved in freelancing, it might be time for some reconsideration.

3. How do you cope with unpredictability and uncertainty?

There’s a true feast or famine situation that occurs for most freelancers. Either you’re swamped under so much work you don’t anticipate ever being able to leave your desk, or you’re left with an empty inbox and an empty bank account, wondering how you’ll be able to cover rent that month.

This means that freelancing can be a real mental and emotional challenge for those creatures of habit that thrive on predictability and stability. Those two words are pretty much the antonyms of freelancing, and it’s important to have an understanding of how you’ll handle that before taking the leap.

4. How do you deal with rejection?

Oh, rejection. It’s definitely one of those dreaded parts of becoming a freelancer. And, believe me, you’ll face a lot of it. It’s all part of the process.

Are you someone who responds so poorly to rejection that it inspires you to want to hide under your desk or immediately burst into tears? If so, you’re going to need to develop thicker skin in order to build a successful freelance career.

Again, this is definitely something you can learn to handle—even if it’s not your natural inclination. But, if that doesn’t sound like something you’re even remotely interested in doing, freelancing likely isn’t the best fit for you.

5. How much do you want it?

Freelancing is awesome—but, that doesn’t mean it’s easy. No, there’s a lot of hard work, dedication, and elbow grease involved. But, it’s worth putting your all into if it’s something that you really want.

So, ultimately, you need to weigh your options and determine how badly you want to make the switch to freelancing. If it’s something you can’t imagine not trying, then you’re bound to make it work!

Kat Boogaard

Kat is a Wisconsin-based freelance writer covering topics related to careers, self-development, and entrepreneurship. Her byline has appeared in numerous outlets and publications, including Forbes, Fast Company, The Muse, QuickBooks, Business Insider, and more. Find out more about her on her website, or connect with her on Twitter.

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