Dreaming of the Freelance Life? Check These 4 Things Off Your List

Here's how I find clients, set rates, get healthcare and more.

Is it your dream to throw off the shackles from your tedious day job? Well, there’s never been a better time to become a freelance worker. As a full-time freelance worker, you’ll set your own hours, choose your working conditions and you’ll never have to ask anyone for permission to go on vacation or just to take a day off.

But as exciting as freelance work can be, the idea can also be scary. Where will your paychecks come from? How will you make up for the loss of healthcare insurance and other benefits? And will you be lonely working by yourself all day? These are the questions that I had to ask myself in 2011 when I left my job as a technical support representative and decided to become a full-time writer. Here’s how to become a freelance writer like me or any type of freelancer you dream to be.

Side Hustle to Full Time: How I Became a Six-Figure Freelancer

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1. Know When It’s the Right Time to Go Full Time

The last thing you ever want to do is quit your job with hopes that you’ll find enough freelance work to make a living. Instead, you should always start by freelancing part-time in addition to your day job, which is sometimes called moonlighting. Once you have established yourself as a part-time freelancer, you need to listen carefully to what the marketplace tells you. If you’re finding plenty of untapped demand for your services from a broad range of clients, then you’ll know that the timing may be right for making the jump to becoming a freelancer.  Or if you start to feel like your day job is interfering with the growth of your freelancing practice, then you might want to make the move.

In my experience, my career at my day job was stagnating, while I kept finding new clients for my freelance writing. Furthermore, my existing clients kept inquiring about my availability to complete more work for them. And finally, my clients didn’t hesitate when I asked them for higher rates — another signal from the market that I used to make my decision.

Make Your Money Work Better for You

Without enough time to take on more and better paying freelance jobs, something had to give, and I knew that it had to be my dead-end day job. When I left my day job, I was just starting to earn nearly as much from freelancing. But more importantly, I was earning an increasing amount every month from my freelance work, while I only received slight raises each year at my day job. It was hard to give up having two sources of income, but it wasn’t long until my freelancing income exceeded my previous salary.

Related: How I Turned My Passion for Writing Into a Full-Time Blogging Career

2. How to Set Your Rates

The rates for a freelance worker are set the same way that nearly everything else is in a market economy. From the salary of your favorite athlete to the wages of a day laborer, supply and demand will determine how much you should charge your clients. If you aren’t getting enough work, then you could be pricing your services too high. But if you find yourself turning away business, then you should raise your rates until you have as much work as you can handle.

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Personally, I take a soft-sell approach to setting rates. I like to speak with my clients and let them know that I’m a great fit for the work they need. Once I’ve established my knowledge and experience, I’ll let them know my rates. If they hesitate, then I’ll let them know that I might have some flexibility, but I’m also happy to refer them to a colleague with less experience that might be in their price range. I don’t get every job I want, but I get enough to keep me busy without selling myself short.

Check Out: How to Get Paid to Do Things You’d Do for Free

3. How to Make Up for Lost Benefits

Perhaps the most pressing concern for those contemplating going freelance is the loss of employee benefits. For example, you may have a generous employer who offers employees a group health insurance plan, a retirement savings program and other valuable benefits. Thankfully, the COBRA law allows you to continue with your existing healthcare plan for usually 18 months after you leave your job. And once your COBRA benefits expire, you can purchase private health insurance through your state or federal marketplace, possibly with tax subsidies depending on your income.

Make Your Money Work Better for You

Another option is a health share plan, which can be more affordable than a standard insurance policy. Health share plans are technically not insurance; they are cooperatives with members agreeing to share each other’s healthcare costs. They don’t cover pre-existing conditions, and there are other advantages and drawbacks worth studying before you make a decision. But after trying a high-deductible health insurance plan, I’ve switched to health share coverage.

Benefits such as a retirement program and other kinds of reimbursements are much more easily duplicated but at a cost. You should add up the value of each of the employer benefits that you’ll lose. Then, consider that value when making the decision to leave your job to become a full-time freelancer.

Know: Ways to Save for Retirement as a Freelancer

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It’s been a long time since I’ve done a daily doodle on my iPad pro and I have to say that I’ve really missed it! • Over the last 6 months I’ve been focused more on client work then I have on my own personal illustration exploration, which isn’t a completely bad thing but I now know that I still have to make time to create for myself. • Whether its doing daily doodles like these, producing podcasts, YouTube videos or courses, all of those are things that I create for myself to share with all of you (and hope you pull a nugget of wisdom out of em)! • I hope that I keep up these doodles and even this style overall and I hope it brings as much joy to you as it did to me in creating this piece. (: • PS: This was created last night while I was relaxing and recuperating from being sick! • • • • • • • • • • • • • #design #artist #illustration #ourtimehasvalue #branding #freelance #instaart #brand #logo #sketches #designspiration #vector #sketchbook #sketch #illustrationstyle #logoinspiration #designtip #adobedraw #adobeillustrator #designeveryday #adobe #thedesigntip #art #artviral #inspirationseed #doodling #doodle #ipadpro #sketchadoodledoo2019
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4. How to Find the Right Work Environment

Once you’ve made the decision to leave your day job and have accounted for all of the employee benefits that you’ll be giving up, then it’s time to think about what you’ll be doing all day and where you’ll be doing it. Some freelancers offer services primarily at a client’s job site, including everyone from painters to some bookkeepers. Others, such as writers, get to work from home or wherever they want.

It can be tempting to work from home, and it’s usually the most affordable option, but is it the best? For freelancers like me, it’s simply too easy to be distracted by the television, the neighbors or even my own family. If you need to get out of your house and find a more distraction-free place to work, there are several options. You can rent your own office, but that can be a little too pricey for a freelancer who is just starting out. Another option is a shared office site or network, such as WeWork, but those facilities might place you in a noisy room full of dozens of other freelancers.

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Not Ready to Freelance? These 11 Major Companies Allow You to Work From Home

In order to enjoy a quiet work environment, I chose to sublease office space from a small business. For just $230 a month, I have my own office with a door, along with access to a printer, fax machine, copier, and scanner. It also includes both telephone and internet service, and I even have a nice view out the window. I found the office on Craigslist back in 2011, and I’ve been with them ever since. Not only is this a great workspace, but I’ve become friends with my officemates. A little water cooler chat has made working by myself much easier over these past eight years.

When it comes to freelancing, don’t be afraid to take it on full time, but be sure to wait for the right time to do it. By taking a look at the marketplace, having a plan to replace your benefits and finding the right work environment, it could be the best decision you ever make.

Click through to read more about how to file self-employment taxes.

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About the Author

Jason Steele

Jason Steele is a journalist who specializes in covering credit cards, award travel and other areas of personal finance. As one of the nation’s leading experts in the credit card industry, Jason’s work has been featured at mainstream outlets such as Yahoo! Finance, MSN Money and Business Insider. Jason’s also well known within the community of travel rewards enthusiasts as the Senior Points and Miles Contributor for The Points Guy and other outlets on the subjects of airline rewards and family travel.

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