Skipping the Free Lane

Let me preface this post by reiterating a simple statement: I have the best job in the world. I wouldn’t trade it for ANYTHING. After all, I took the time last week to explain why freelancing is the most amazing concept in the world. But, in all fairness (that’s such a terrible concept, isn’t it?) I now need to bring the excitement level down a few notches.

That’s right, lasers and jellybeans, it’s time for the crash. (Feel free to boo – I know you want to)

Why You May NOT Want to Freelance

No one likes to think about the “negative” side of things. And I want to make sure I clarify that these little snags aren’t necessarily BAD – they’re just less glamorous than the shiny bubbles I mentioned before. If you can swallow them, then you’re good to go. I just have this obligatory, guilty conscience prodding me to make sure I put ALL of the information out there. (That tiny creature in the back of the mind is annoying, by the way)

1. Organize or Die

Remember getting to stand on your own? No boss except you? That means all responsibility also falls to you. No one else keeps your shit together. Assignments come with deadlines, some come with templates, and all come with specifications. You have to keep track of ALL of those details. Slip up, and you’ll screw an article. Unhappy clients don’t pay you. If you’re part of a job board such as Upwork, those clients submit poor ratings that get published on your profile for potential clients to view. Guess how many want to hire someone with a poor performance review?

You can’t be the kind of person who “wings it.” You’ll end up overwhelmed and sink FAST. I use a TON of tools to keep my work streamlined:

• Color-coded white board calendars
• Excel spreadsheet of ALL assignments (also color-coded)
• Evernote
  • Every client has a notebook
  • Each assignment is an individual notecard
  • All mandatory information gets bolded at the top
  • I create a checkbox with due dates (and cards are in order of due times)

Color-coding assignments by client makes my life a THOUSAND times easier. A quick glance at the calendar tells me who’s work is due when. The system allows me to usually finish my work early. I’ve definitely never missed a deadline. Can you hire a virtual assistant to handle all of this for you? Sure – but that’s money out of your pocket. The choice is yours.

I don’t have a 100% satisfaction rating and a solid string of five-star reviews for nothing.

2. Paperwork

You WILL need to do homework. That means investing in some books. If you can, talking with people who’ve done the groundwork helps, too. Freelancing is WORK. That means filing paperwork. Why? Because the government still wants taxes. And guess who has to file them? That’s right – you. You’re your own boss, remember? No one else is going to do it for you.

I lucked out. An awesome friend dumped two vital books in my lap and shoved me off the cliff as a start. I also had friends and family with their own businesses. They gave me the information I needed to set up my sole proprietorship. Every city and state is a little different, so make sure you look up the rules where you live. Just remember, as the money rolls in, YOU have to set aside the tax portion. YOU have to keep track of your client contracts. YOU have to be ready to juggle all of those W-2s come tax time (or fork over more cash for an accountant to do so).

It sounds overwhelming, and if you don’t do your homework, it WILL be. Once you have the basics under your belt, you’ll be fine. But you don’t have a boss or corporation to handle that pesky paperwork for you anymore. And when you’re used to someone else handling the tedious chores, it can get irritating.

3. Got a Healer?

Know what else you sacrifice as a freelancer? Insurance. Well, in theory. Basically, you just lose the comfort of a job that COMES with insurance. Freelancers don’t have a cushy life, much as society likes to think we do. In fact, if you poll most writers, they’re rampant with chronic illness. Most artists, in general, suffer from chronic disease and even cancer. And we don’t have the safety net of job-funded health insurance.

You have a few options:

• Get a bubble (just kidding)
• Find insurance on your own (watch your pennies)
• Get on your spouse’s/partner’s insurance
• Roll the dice and hope you never need insurance (may the odds be ever in your favor)
• Start a GoFundMe

This is one of the biggest drawbacks to being a freelancer. Because healthcare in the U.S. SUCKS! Even WITH insurance, health costs get ridiculous. And if you fall ill and can’t complete your work? You’re out income. It’s a dangerous game. You need to take care of yourself (which is why you get my Dead Pool posts). And, honestly, you need to find a way to get yourself insurance. The risk is too high.

4. Motivation

You’re the boss. No one can MAKE you do the work. Except you. If you don’t “feel like it,” nothing gets done. Which means you don’t complete your assignments, and you don’t get paid. No biggie. Freelancers can’t have “off days.” You can’t submit sub-par work. If you aren’t at your best, you have to step up and tell a client you need more time. It requires a level of frank honesty that you didn’t have to present at other jobs. (Face it – were you always as sick as you claimed? I know for a fact people I worked with lied through their teeth)

You don’t want your reputation to slip. Your work is YOU. You’re representing yourself on a public platform in a way no other job really does. And lazing around doesn’t work. No one’s going to walk through your office and bang on the desk to urge you to get to work. (Okay, so I have a tiny demon that jumps on my desk, but it’s not really motivating)

You have to have an inner drive to get up and work every day (or whatever you set your schedule to). You need to tackle every assignment with the same level of enthusiasm. If you can’t, don’t accept the work. It’s better to turn a job down then submit half-assed crap.

5. What’s a Vacation?

Surprise! Freelancers don’t get time off. Not officially, anyway. No paid vacation, no paid sick leave. Sorry. You DO make your own schedule, so you can elect to take time off whenever you want. You just won’t get paid for that break. So consider those vacations wisely.

If you’re a writer, you CAN use trips to a certain advantage. For instance, you can pitch a story to a magazine centering around the location, the activities you’re planning, etc. The fact you’re not asking them to foot the bill for the trip AND already planning to have boots on the ground helps to sell the story. You just need to make sure you choose the appropriate market and find a unique angle for the story. And you need to realize there’s a good chance they’ll reject the pitch.

Tempering the Excitement

Freelance writing IS the best thing that ever came into my life. It just came with strings attached. (Newsflash: everything does) If you want to follow your freelance passion, make sure you shine a light on EVERY aspect of your chosen path. If you know where the pit traps are, you’ll be better for the journey. You may still fall into them, but you’ll have a better chance of climbing out the other side.