6 questions to ask yourself before you go freelance

Here's what working for yourself could mean for your finances — and your daily life

Freelancing.
(Image credit: iStock)

When I walked out of my office six months ago, I had no idea if what I was about to embark on was even going to work; but I had to do it. Leaving behind 17 years of a very stable, financially secure career felt irresponsible — especially to go freelance. Questions swirled in my head those first few months: Did I make a mistake? Do I have the personality to stick this out? What happens if I can't make enough money? What about my retirement? And the one doubt that seemed to always invade my thoughts: Was this the right time to make a major life decision?

But here's the thing: There is no perfect time to change careers. Chances are, if you wait for that "golden moment" to make your move — when everything feels just right — you'll be plugging away at your current job until you retire. So, before you pack up and give your boss notice, take some time to honestly answer these six questions to determine if you're ready for a full-time freelancing career.

1. Can you work from home?

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This is often one of the main reasons people choose to go freelance. The flexibility and affordability of using your home as an office has many positives. However, working from home also comes with its fair share of challenges. Establishing an office space to work from is essential. Also, being able to ignore (or at least minimize) the urge to finish the laundry, empty the dishwasher, or take a nap requires you to put work first. If you want to be efficient, maximize your financial gains, and meet your deadlines, you have to give your job just as much attention at home as you would if you were in an office.

2. Does it suit your personality?

Are you a self-starter? Can you manage your time and stay organized? Making the leap to go out on your own definitely requires a whole lot of patience, perseverance, determination, confidence, and the right mindset. After all, when you sit down in your new office, it's just you and the computer; there's no one else that's going to secure clients and make the deadlines. Being self-employed requires you to perform and produce, all the time. Another point to consider is if you are an extrovert who thrives in a work environment full of other people, then you may find freelance a lonely living. Seeking out social interactions by joining a local business group, writers group, or a professional network group can help alleviate the isolation and keep you connected to people.

3. Do you have another source of stable income?

If you are venturing out on your own, do you have a healthy savings account already established? Ideally, you will have three to six months (some experts even say up to a year) of income set aside in a separate account. This helps create a financial buffer in order to get through those times when the work is on the slow side. And even if you have a spouse or partner who can help support this transition, most experts will tell you this cushion is important for anyone leaving a financially secure job.

4. Are you ready to be a business owner?

You're not just a freelancer, you're also a business owner, and you have to think and act like one. Quarterly taxes, invoicing, spreadsheets, chasing down late payments, hustling work, and recognizing that being the sole source of revenue for the business is a heavy burden to take on. Additionally, if you're used to a steady stream of income and the cushion that comes from having sick leave, vacation time, health benefits, and retirement, then get ready for a major wake-up call. You have to plan for these expenses and allocate a certain percentage (some experts say up to 40 percent) of your gross income to cover those benefits. And when the checks do start rolling in, you absolutely must remember to set aside a percentage of your income for quarterly taxes (often 25-30 percent).

5. Can you try it on for size before leaving your current job?

One way to find out if you're ready to make freelancing a career is to try it out before you quit your job. Start pitching publications and businesses, and establishing relationships. Depending on how much time you have, consider taking on five to 10 hours of work a week. Not only does this help you ease into the freelance life, it also allows you to have your business set up and a professional network of clients identified that you can reach out to when you go full-time.

6. Will you be able to handle the financial ebb and flow of freelance work?

What happens when you tell someone you're thinking about going freelance? Chances are, the term financial stability is thrown out within the first few minutes of the conversation. Before you turn your world upside down, make sure you fully understand the financial instability of freelance, and have an idea of how you're going to push past the feast or famine mentality to create a business that is stable and profitable.

Consider this tip from Jenny Beres, a hugely successful copywriter and content strategist: "When you're starting a freelance business, it's important that you understand the lack of clients can directly be traced to a lack of consistent marketing and reaching out," she says. "This is not hard all in itself, but it's the emotional roller coaster that derails people for a week at a time — and you simply don't have the time to do that," she says. "Head down, pitch everyday, leverage your network, and remember that what you do everyday will determine what your bank account looks like."

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Sara Lindberg

Sara Lindberg is a freelance writer specializing in health, wellness, education, and business. Her work has been featured in The Washington Post, Headspace, LIVESTRONG, Paste Magazine, GOOD, and many more.