12 Questions You Should Ask Yourself Before Going Freelance

Thinking about joining the ranks of the self-employed? Becoming a freelancer is a major move in anyone’s career, and there are some important questions your should ask yourself before going freelance full time. Freelancing can be rewarding in a lot of ways, but it’s not for everyone. It’s essential that you take the time to really assess how moving away from the standard 9-to-5 work model will affect you before you take the plunge into the freelancing pool.

You’re not the only one considering a move into freelance work. According to a 2015 survey by the Freelancers Union, over a third of the U.S. labor force (almost 54 million workers) currently does some kind of freelancing. Some of those people freelance in addition to full time, salaried jobs, but 19.3 million do project-to-project contract work full time, and another 14.1 million get by doing a variety of jobs (For example, someone might have a regular part time job, coupled with a freelance jobs on the side).

Although we seem to be increasingly moving toward a freelance economy, only you can decide if becoming an independent contractor is right for you. There are some real perks to freelancing, including setting your own schedule and getting to wear sweatpants to work, but there’s a lot of risk, too: You won’t have a guaranteed, steady paycheck, health insurance and other benefits, or paid vacation days. You’ll also essentially be running a small business on your own, and will have to deal with things like tracking down payments owed to you and dealing with the complicated business of freelance taxes.

So before you quit your day job to begin freelancing full time, start with these key questions:

1. Are you self-directed?


Being a freelancer means that you no longer have a boss setting your schedule or telling you what to do, which is great. Independence! But the truth is that some people need to have someone directing them. Some people are great at being self-disciplined, making themselves work (even when they don’t want to), working without anyone checking up on them, and giving themselves assignments. But some people really aren’t — they need an external structure to give shape to their days, they need some direction, and they want to be able to get feedback from a coworker or supervisor. And if that’s you, that’s totally OK — it’s not some kind of moral failing; it’s just a different mode of working. If you don’t think you can be productive or happy doing completely self-directed, self-motivated work, then freelancing may not be for you.

2. Are you (very) organized?


When you work for yourself, you don’t have the infrastructure that a larger business would have, and so it’s up to you to stay organized and on top of things. You’ll have to be able to keep track of all the different projects you’re working on at once, budget your time for each one, meet deadlines, and be able to organize your finances. A lot of freelance industries cater to creative people (writers, designers, etc), but those who are successful are the ones who are also able to keep their businesses in order.

3. Are you OK with working alone?


Being a freelancer doesn’t necessarily mean that you have to work at home alone (coworking spaces exist!), but you won’t have the communal working environment that you may be used to. I work from home by myself (Well, with a dog. That’s a perk.), and, on the whole, I love it — no commute, no dressing up, no distractions (Er… except for the ENTIRE Internet). After a number of years of doing self-directed work of different varieties, I’m also very used to it at this point. That said, working at home alone is a challenge sometimes, even for me — it can be easy to lose focus, and sometimes it gets straight-up lonely. If you have a partner who works outside of the home, you can also run into trouble because he or she will come home and want to be quiet and relax, and you’ll finish your work day and think, “Hooray! Time to get out of the house.” Again, I like working from home, but I’ll fully admit that, being alone all day, I get a little weird sometimes.

4. Are you OK with long hours?


Freelancers often have to work long hours in order to make ends meet. You may also have an inconsistent workload, with not enough one month, and more than you can handle the next. Although you may save time by eliminating your commute and skipping the endless array of staff meetings you had to attend in a traditional job, you’ll probably spend more time chasing down clients, managing the business end of things, and doing your actual work.

5. Are you willing to do the unpaid labor of freelancing?


This will vary from field to field, but a lot of freelancers end up doing a lot of work that isn’t actually paid. If you’re a writer, for example, you’re going to spend many hours developing pitches and contacting editors. Of course, the hope is that this work will eventually translate into paid work, but it can certainly feel thankless when you’re in the thick of it.

6. Do you already have a foot in the door?


As a freelancer, it will fall on you to find clients. That job will be easier if you already have some experience in your field and some contacts you can use to drum up business. If you’re new to your industry and don’t know anyone, that doesn’t mean that you can’t make a living as a freelancer, but it will be harder at first. And you’ll have to be committed to building a network, which brings me to…

7. Are you a networker?


Some people are naturally good at networking and making connections with people. I’ll be honest: I am not one of those people. Even the word “networking” fills me with a vague sense of nausea and dread. Networking is scary: You’re approaching people you don’t know and braving the possibility of extreme awkwardness, if not outright rejection. But if you’re going to freelance, you’re going to have to bite the bullet and get over that fear.

8. Are you OK with instability?


No job is ever completely guaranteed, but freelancing has an extra dose of instability and unpredictability. Some months you might have plenty of work, others you might not have enough; your schedule might change dramatically from week to week; and, even when you have money coming in, it might not always be on the clockwork schedule of a traditional paycheck. People who have been freelancing for a long time and have built a robust clientele will have a more steady income stream and schedule, but starting out (and for years after), you’ll have to be OK with some instability in your life. That’s not necessarily a bad thing — the beauty of freelancing is that something great can be just around the corner. But the anxiety that comes with not know exactly where your rent is coming from next month is a lot to handle.

9. Are you assertive?


I think freelancing attracts a lot of fairly introspective people, but to make it work, you have to be able to stand up for yourself, forcefully, if need be. In addition to selling your services to clients, it’ll be up to you to make sure you get paid.

10. Do you know anything about running a business?


As a freelancer, you won’t have an accounting department to manage invoicing, payments, budgeting, taxes, or other financial matters. You don’t have to have an MBA to do freelance, but you’ll have to be dedicated to learning as you go — after all, you’ll essentially be a one-person shop.

11. Do you have any kind of financial cushion?


If you’re just starting to freelance full time, it may be a few months (or even longer) before you’re able to financially sustain yourself. Do you have the financial resources to make it through those leaner times? Freelancing (like most things in life) is a gamble, but you’ll sleep better at night knowing you have some cash saved in the bank.

12. Have you ever freelanced before?


If you’ve never done any freelancing before, you may want to dip your toes in the water before committing to it full time. If you currently have a full time job, try picking up a couple of freelance projects to do at night or on weekends — not so many that you have no time to sleep or live, but enough to give you an idea of what doing this work on your own might be like. Freelancing on the side may also help you build up a clientele and even a few steady jobs, so that you’re not starting from scratch when you do decide to go for it full time.

If these questions sound daunting, don’t panic. Freelancing offers a lot of benefits that, in the right circumstances, can more than make up for the challenges posed by working independently. Just be sure to go into it with a thoughtful mindset and open eyes.

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