6 important questions to ask yourself before going full-time freelance

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A 2016 study found more than 35 percent of the American workforce are freelancers. If the temptation to dictate your own hours, work from wherever your wanderlust inspires you, and explore freedom within your career is growing by the hour, it’s important to make sure you’re fully prepared for the switch. As career coach Cheryl Palmer says, many people feel overly optimistic about their ability to provide for themselves, without realizing how much work, dedication, and, um, hustle, it takes to truly find steady success as a freelancer.

There is more stability in working full-time than in freelancing. Not only is there steady work, but there are also benefits such as health insurance and paid vacation time that usually come with working full-time,” Palmer tells Yahoo Lifestyle. “Freelancers have to generate enough work at a high enough hourly rate to replace the income that they would make working at a full-time permanent position. This is a big enough move to consider if you are single with no dependents, but if you have other people depending on you, then this decision is of even greater import.”

Before you put in your pink slip and book a one-way ticket to the digital nomad hub of Bali, career experts recommend asking yourself these questions first:

1. Why do I want to freelance?

Seems simple enough, right? Not always, according to Palmer. Plenty of people find themselves in a stressful quarter — with a manager passively-aggressively following up on projects, say — and decide to throw in the towel without thinking about it. Hold your breath and bite your tongue and get real with yourself, Palmer advises. You can begin by writing down all the benefits you can’t get from a full-time, permanent position that freelancing can offer you. As Palmer notes, you need to get clear if your intention is a stopgap measure or an actual shift in your career path that you’re committed to for the next few years.

2. Am I ready to change, well, everything?

Here’s the deal: Going freelance full-time isn’t just about becoming the captain of your career, but a move that will change every single aspect of your life, says brand and career coach Colleen Star Koch. While past decisions might have included how much you’d contribute to your 401(k), when you’d take your vacation, and what to claim on your taxes, now you’ll be making choices left and right about your finances, your career goals, your health care provider. The list goes on (and on). “Being a person is pretty challenging already. You have to pay your bills on time, take care of your physical and mental health, make your own appointments, and actually take your doctor’s advice. You have to make time for your relationship, friends, and family,” she explains. “When you take the step to start freelancing full-time, you are also in charge of defining and maintaining your brand, finding and keeping clients, handling your own business taxes, and your own accounts payable and receivable. You have to do your own marketing and social media. And I’m just getting started. It’s a big responsibility!”

Though Koch says it’s a 100 percent attainable goal, it’s one that requires you to start small and work your way up and accept that it will likely be quite the turbulent shift. “You have to know that you have it in you: inner strength, confidence, and drive to take on being in charge of your whole life. If you do, get ready for an amazing ride,” she says.

3. Do I have enough savings to last me six to 12 months?

Even if you’ve been working round the clock to build up your side hustle (while also working full-time), the moment you let go of your professional safety net, you’re on your own. And while you might have clients now, Palmer is quick to remind wannabe freelancers that tables can turn at any moment, and competition is often fierce. That’s why having a cushioned savings account will save you a lot of stress and worry, as you experience periods of downtime before the flood of a financial upswing. “Once you develop relationships that will bring you steady work, you should be fine. But until that happens, your bills will continue to come at a steady pace. Are you prepared for the time that it takes to ramp up?” she advises.


4. Can I run my own business?

So you’re a talented writer with an impressive vocabulary that comes naturally and easily to you. Or you have a knack for photography or event planning. While Koch says plenty of people have a talent, a special service, or a great idea for a product or company, those skill sets don’t always translate into the ability to be a sole proprietor. In addition to exercising your creativity, you also have to study up on marketing, social media, legal practices, taxes, analytics, networking — and every other nook and cranny of a company.

Though you don’t have to be a pro at everything, you do have to be willing to roll up your sleeves and put in the work to figure out solutions that might not come naturally to you. “There are tons of tools and resources out there to help you, but if you aren’t comfortable doing the work to find the resources, learn the tools, figure out the tricks of the trade, and take responsibility for all these different aspects of running a business, it might not be your time to jump into freelancing,” Koch tells Yahoo Lifestyle.

5. Am I ready to network?

Regardless if you’re starting a consulting company or becoming a full-time project manager for a variety of clients or a solo nomadic engineer, without your network your business doesn’t have a fighting chance, according to Koch. And if you’re still growing your community, know that coffee and happy hours, cold emails and calls, and going to plenty of events are all part of the freelancer’s job. In other words? Get ready to put in a lot of effort to build meaningful connections.

“This means developing mutually beneficial relationships with a wide variety of people, not just meeting people, handing them your business card, and asking them to buy your thing. If you have a great starter network, however, and you’re prepared to commit the time and energy it takes to build relationships, invest in others, and exceed expectations when you’re lucky enough to get support, then you have one one of the most fundamental ingredients to successful freelancing,” Koch says.

6. Am I comfortable with uncertainty?

Many factors contribute to the plethora of work or drought of work you’ll have throughout the years as a freelancer. From seasonality and budgets to industry shifts and other factors, you might feel like you’re excelling one month only to have your income slashed in half the following. It’s all part of the ride, the experience, and the job description of independent working. That’s why Koch says it takes a risk-tolerant personality type to become a freelancer, as those will be the people most adept at surfing the inevitable waves and breaks without getting frazzled or disenchanted. It takes the kind of confidence that allows you to know, deep down, that you can make it through a tough spot. It takes an adventurous spirit who is in it for the story as much as the success,” she says. “You have to be able to function even when you’re afraid of failing and to use that fear as information, and take the steps needed to resolve the issue at hand.”

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