1. Are you a self-starter?

Most people like the idea of being a freelancer because it means they get to be their own bosses. This is a noble pursuit; the joys of setting your own hours, making your own money, and directly communicating with your own clients are manifold. Unfortunately, being your own boss also includes the darker side of management. You have to be able to get yourself to work “on time” each day. You have to be able to do unpleasant tasks when the time calls for them. And sometimes, you have to be a jerk to get your employees (namely, you) to do what needs to be done.

2. Can you handle the “business” side of the business?

Freelancing—whether you are writing, designing, or even providing cooking advice—calls for more than just doing what you love to do. There are invoices to create, clients to find, emails to handle, accounts to balance, taxes to pay, paperwork to be filed, follow-up calls to be made, and organization to be done on a variety of levels. For freelancers, being good at your craft is simply not enough; you have to be a manager, bookeeper, receptionist, and quality control department, as well.

 3. Is this going to be a career or a hobby?

Picking up a few clients in your spare time can mean one of two things: you are beginning a freelancing career or you are dabbling in something you enjoy. While there is nothing wrong with either one of these choices, each one will ultimately lead you to a different path.

4. Do you have a support network?

This support network can take on a variety of forms. For parents, it may mean having reliable sitters to help with child care. For beginning freelancers, it may mean having a steady income from a spouse or other interested party. For me, it means having a business partner. For many of us, it also means having an online community that can provide support, advice, and important contacts.

5. Can you handle the technology?

This extends beyond simply using a computer, fax machine, or conference setting on your phone. Do you know how to navigate the internet to make connections and find jobs? Can you build and/or maintain a website? Do you know how to advertise online? Can you figure out wordpress without getting a major headache (still working on this one myself…). If you can’t do any of these things, do you know where to find someone who can? Although there are numerous freelancing opportunities in print media and in local businesses, some of the easiest and well-paying jobs are found online. You have to be able to compete.

6. Is your work an art or a craft?

I’m mostly thinking of writers and designers here. Someone whose work is art—that is, it is accomplished for the beauty of the thing—is going to have a much harder time finding pay than someone whose work is meant to make money. While there is infinite value in art, and while some people can make quite a bit of money this way, most of us are not going to be hitting it big anytime soon. Writing or drawing for clients, for businesses, and for maximum sales—though certainly less glamorous—is what makes up the bulk of freelancing.

7. Can you meet deadlines?

Are you able to create realistic timelines? Can you look at the big picture and really determine if you will be able to meet all of your responsibilities? The ability to manage your time and meet the demands of others is essential in keeping your clients happy and well-paying.

8. Do you have an exit strategy?

If you are just jumping in to see if freelancing “fits,” you need to make sure that you look past what you are doing today or tomorrow. If you are really going to be successful, you have to be able to think big and think long term. This includes looking 10, 20, or even 30 years down the road to see where you want you and your business to be.

9. Do you have the education?

It doesn’t matter if you were educated at an Ivy League college, a local state party school, the real world of business, or in the car while you waited for your kids to get out of soccer practice. If you don’t have the skills necessary to compete in whatever your niche may be, you are going to find it hard to set yourself apart as someone worth hiring and keeping.

10. Are you ready to change your life?

Images of freelancing often include sitting comfortably in your pajamas in the late morning, having just woken up from a good night’s sleep. This sounds like a life change that just about everyone could enjoy. However, the real world of freelancing requires a little bit more. You have to learn to juggle home, family, and work. You have to continually perfect your craft. You have to control your own actions and take responsibility for everything you do. You have to consider this a serious profession that can support you and your family for years.

Then you can start working in your pajamas!

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