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7 Signs You’re Not Yet Ready to Quit Your Day Job

by Leah Rutherford | The Web Writer Spotlight: Jul 18, 2014

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So things are going pretty swimmingly in your freelancing life - the opportunities keep coming in, the extra income is awesome and you’re starting to wish that you had more time to fit in your independent work. Maybe you’re even thinking about cutting back your hours at your day job, or taking the plunge and striking out on your own.

Quitting your job to pursue your talents and passions is not a decision to take lightly. In most cases, the choice is final; there’s no magical undo button. Take a look at the following seven warning signs that could mean you’re not ready yet. If you recognize these red flags in yourself, it may be wise to reconsider your dreams of freelancing full time - at least for now.


1. You don’t have a plan


When you picture quitting your job, maybe you imagine the triumphant exit you’ll make, or you relish the thought of never having to fill out another report ever again. But what comes next? If you don’t have a clear plan for how you’re going to expand your freelancing business into a full-time career, it’s best to keep that dream on hold for a little longer, until you’ve worked out the details.


2. Your finances aren’t in order


Things are going to get really lean, really fast—especially if you’ve got a lot of high monthly expenses. Now is the time to cut the gym membership you never use and stop eating at restaurants multiple times a week. If you haven’t been saving up, get used to the idea of your day job, because you’ll need to be there for a while longer.


3. You don’t self-motivate very well


How good are you at motivating yourself to work hard? At your day job, someone else is probably calling the shots and telling you what to do—and your motivation is to not get fired! When you’re in charge of yourself, it can sometimes be hard to force yourself to work. If you struggle with productivity problems, you might not be ready to call it quits just yet. Focus instead on becoming more self-motivated so that you’re ready to be your own boss when the time comes.


4. Your business doesn’t feel legitimate


Do you have a tax ID number for your business? Do you know what kind of bookkeeping you need to do to stay on top of things come tax season? Or are you planning on throwing all your receipts in a box and letting an accountant do it for you? If your freelancing business still feels like a hobby instead of a real business, you might have some work to do before you are ready to go at it full time. Try reading up on the ins and outs of starting your own business and doing taxes as a self-employed individual.


5. You don’t feel like an expert


If you’re going to take the plunge, it’s going to require more than a passing interest or novice understanding of your craft. After all, if your dream is to blog about classic cars, specifically Mustangs, but you don’t even know how to identify different Mustang parts or where to buy them, you’ll still need to do some learning. You won’t be providing your readers useful information if you don’t have expertise in your niche, so don’t quit your day job if you still feel like a novice in your dream job.


6. You don’t have reliable customers


Sometimes the going is good, and the work is easy to come by. Other times, you hit a dry spell, and it seems like you’ll almost take on any project just to get a little cash. If you haven’t built up a great base of customers yet—repeat business is some of the best business you can get—then it’s worth your while to do it before you leave behind your reliable paycheck.


7. Your heart isn’t in it


We all doubt ourselves from time to time, and it’s completely normal. But if you are thinking about pursuing your freelance work full time out of a sense of obligation or because you feel like it’s expected of you, you’re not doing it for the right reasons. It’s still perfectly understandable and legitimate if you want to keep freelancing in your free time rather than as a career, and no one should make you feel bad about it.

If you see these red flags in your freelance work, work on the problem areas before you quit your day job. That said, note that sometimes the time is just right for following our passions—especially if you have some emergency funds saved up, you can’t stand your day job, or you have a support system there to help out if your dreams don’t work out quite the way they should.

See Also: 10 Tips to Transition Smoothly into Web Writing


Leah Rutherford, a resident of Chicago, is a freelance writer specializing in career development, especially in the field of writing. She also blogs about small businesses startups and the job search process , which you can read on her blog, JetFeeds.




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