The Truth About Freelancing

The media is filled with “be your own boss” stories. These articles extol the virtues of charting your own course, saying no to corporate restrictions and deciding to live life your way.

This all sounds great, right? Who doesn’t dream of tossing their alarm clocks, their corporate wardrobe and all the other restrictions that go along with calling someone else boss? These dreams also usually involve being on a sandy beach with a laptop…wearing a bikini and sipping an umbrella drink while you “work.”


This is NOT me! But it IS what I thought freelance writing would be like…once upon a time.

If you believe that, then you’ve never run your own business. And if you have not, but nurture secret dreams of doing so, you need to read this. Not. Even. Kidding. Read it. Now.

Finally, a realistic look at what it is really like to be a freelancer. An entrepeneuer. Whatever you want to call it.

And if you read it and still think going out on your own is right for you, make sure to also ask yourself a few more questions. Put to you by someone who has “been there, done that”…like…

How do you feel about a bad night’s sleep? I’m not sure I’ve drifted off into continuous, peaceful slumber since I started freelancing. If I’m not worried about where the next project is coming from, I’m thinking about outstanding invoices or coming up with new pitches for editors. Or wondering how the bills are going to be paid this month. No matter the pitfalls of working for someone else, I’m pretty sure there is a direct relationship between a steady paycheck and 7-8 hours of consecutive sleep at night.

How’s your self-confidence? Freelancing is filled with rejection. No matter how great you are at what you do, you will inevitably be told no more than you’d like. Or were ever used to before. It doesn’t necessarily come your way because you’re not good, but it sure can feel that way some days. It can shake even the most confident and talented individual to the core on occasion. If you are not a fan of self-doubt…well, nobody is. But when you are pounding the pavement to find your next project, just know you have to learn how to shake it off. Or you will go crazy.

Are you a fan of steady money? Directly related to point #1, it can really be feast-or-famine when it comes to earning bank as a freelancer. Some months the income flows like water down a snowy mountain in spring. Other months, it seems like you’re stuck in the middle of Death Valley slowly dying of thirst. Yet your monthly bills never fluctuate like that. Therein lies the rub. Those dry months you forget about the stress of working for someone else, and recall with fond affection your days as a corporate worker bee when you joyfully saw a consistent direct deposit in your bank account. Every month. Like clockwork.

So what’s the moral of this story?

It isn’t to say that freelancing isn’t a viable career option. It is. I like it and the freedom it gives me. I’m wearing pajamas as I write this. And doing laundry. And it is 9:00 a.m. on a weekday. I can work anywhere (theoretically anyway…realistically only to my local coffee shop, as finances may dictate I go no further than that). It is also really satisfying to receive positive feedback from a happy client, and know that the feedback is directly related solely to my work.

But freelancing is also one of the most stressful “jobs” I’ve ever had. And I was a divorce attorney, so that is really saying something. It’s a good thing I thrive on stress. This is actually the perfect job for me.

Now where’s my bikini. And a warm, sunny beach?






One thought on “The Truth About Freelancing

  1. Pingback: The Truth About Freelancing – Part 2 | Island Girl Writing & Consulting

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