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Advice / Succeeding at Work / Changing Jobs

4 Questions to Ask Yourself Before Quitting for a "Dream" Freelance Career

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I’ve been a full-time freelance writer for nearly three years now. As a result, I hear from a lot of people who are aiming to start freelance careers and are looking for a detailed answer about exactly how I made it happen.

Beyond attempting to get their hands on a supposed black and white formula for success, I find that many of them are simply seeking reassurance—they want to know that they too can quit their jobs and make it work.

Here’s the thing: That’s not a promise I can make. Everybody’s situation is unique, and whether or not you’re able to make a go of it as a freelancer depends so much on your own determination—and a little bit (alright, a lot) of luck.

What I can do, however, is give you a bit of food for thought to help you determine your next steps. If you’ve been considering leaving your job in favor of pursuing the freelance life, here are a few things I encourage you to consider before jumping ship.

1. How Comfortable Are You With Instability?

Chances are, you’ve heard of the notorious feast or famine phenomenon that comes along with freelancing. When things are good, they’re really good. But, when they’re bad? Well, they can be really bad.

Because you’re responsible for finding your own projects and clients, your workload, income, and—as a direct result—your confidence can fluctuate even more than you can imagine.

For some people, that’s exciting. But, for others, it’s panic-inducing. So, instead of just acknowledging that these ups and downs exist, it’s important to take the time to think about how you’ll cope with them—both financially and emotionally.

If you’re someone who needs predictability and stability in order to thrive? You might not adore freelancing as much as you’re assuming you will.

2. How Much of a Self Starter Are You?

I always thought of myself as extremely self-motivated. But when I started as a freelance writer, I realized I needed to kick that quality up about eight notches.

Freelancing doesn’t just require you to be a self starter—it requires you to be an extreme self starter. Your livelihood rests solely on your shoulders. You need to chase down work, network without shame, and put yourself out there for projects that might terrify you.

And, you need to do that all with little to no direction or pressure from a boss who’s impatiently tapping her foot.

I’ll be the first to admit that can be paralyzing, and not everybody’s equipped (or even willing!) to be so aggressive and disciplined.

3. Why Do You Want to Freelance?

This is usually one of the very first questions I ask people who approach me for freelance advice. More often than not, the responses I receive look similar.

“I want to be able to work when and where I want. I don’t want a boss anymore. I don’t like what I’m doing right now and I need an escape.”

Do you know what I don’t hear that often? Something that goes like, “I’m really passionate about this work and think striking out on my own would be challenging and rewarding!”

People are always quick to cite the things that they don’t like about their current situations, rather than what they’re hoping to accomplish as freelancers. They look at the lifestyle as their ticket to finally work in their pajamas and have flexible schedules.

However, if you’re seriously considering freelancing as a career path, it’s important that you recognize there’s a lot more to it than that. Ensure that the reasons you want to take this road extend beyond the superficial clichés, and you’ll be a step ahead of most people already!

4. What’s Your Back-up Plan?

I’ll be the first to admit that I’m hardly the person to lecture you on back-up plans—I bid adieu to the security of my full-time job without so much as a loose strategy in place.

It worked out. But that doesn’t mean that I’d recommend you take the same approach.

What happens if you try it, and you can’t make ends meet? What if you give it a whirl and decide you hate it? What will you do if your circumstances change and you realize you need a full-time job that offers benefits?

Perhaps you’ll secure a part-time job to subsidize your income. Maybe your partner can afford to carry you financially for a while. Or, perhaps you’ll give yourself a certain amount of time (six months, a year) before you decide it’s time to head back to a more traditional career.

Regardless, I think it’s smart to have at least some inkling of what you’d do if this leap doesn’t pan out in your favor. Things change, and one of the only certainties that freelancing brings with it is this: uncertainty.

Quitting your job to pursue a freelance career is a big decision. And, while it’s impossible to predict exactly how things will play out for you, you want to be sure that you give this decision the time and careful consideration it deserves.

Start by asking yourself these four key questions, and you’ll gain some clarity about whether or not it's truly the best move for you.

Considering waving goodbye to your nine to five and saying “hello” to the freelance life? Tweet me and let me know!