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.

I won’t lie: I have the best job in the entire world. In my down time, I marvel that it took me so long to get my act together and start on this path.(Here’s a huge secret, lasers and jellybeans: if you have a dream – GET TO IT!) That’s how fantastic my life is. And, so , out of purely educational purposes, I’m going to run through all of the reasons you might consider making a similar career choice.

Why You Want to Be a Freelance Writer

When I first ventured into the freelance world, I wrote a sample blog article about working from home. Of course, now most people are pros at working from home. That ISN’T one of the points I’m going to hit on (exactly), though it’s certainly a perk. Nope, I have five other reasons to delve into.

1. You Get to be You

While I fully admit I’ve never worked in the food service industry (which is for the best, as I lack the grace and dexterity required), I’ve worked in most other industries in the past. They all have one thing in common: soul-sucking requirements placed by management. Uniforms, rules about tattoos/piercings/hair, and restrictions on office decor. It’s conformity at it’s worst.

When you freelance, all of those little nit-picky details float away. Case in point: for work today, I’m wearing Harley Quinn socks, comfy shorts, and a Bruni tanktop. (And before you snicker about my being a slob, all of them have purple on them – so there) The majority of my clients communicate via direct messaging or email. Which means I have the freedom to dress exactly as I want. My personality gets to shine. I can experiment with whatever hair color I want and play around with my pixie cut. I tossed out my boring, practical tennis shoes in favor of adorable Demonia Cult shoes. My geeky wardrobe might raise eyebrows out in public, but it makes me happy and keeps me smiling.

My office is ME. (I promise, photos will come as soon as the new prints I ordered arrive and get framed) Oh, sure, I have reference books on my shelves, and there are sticky notes, notebooks, my whiteboard calendars, and pens (well, at least one that Tonks hasn’t stolen) present at all times. But I also have tiny stuffed animals, Funko POP! figurines, shark teeth, and signed photos and posters from my theatre days. I don’t have to suffer with the decor foisted upon me by others. I get to decide what I want to have around me, channeling my creativity. It’s the best kind of freedom!

2. You’re the Boss

You decide who you want to work with. At this point, my work schedule is full. (I’m not exaggerating, either. My calendars – yes, I had to break down and buy a second one so I have two months up at a time – have up to three assignments due every day) While I still duck onto the job boards and submit proposals here and there, a lot of my work now comes in through invitations. (Awesome feeling, by the way) I make the calls on what I accept.

If you don’t want to work for a certain price, you can make that call! If you don’t want to accept a job, you have that choice! You hold the power to make all of those decisions! There’s no weight sitting on your shoulders, telling you you have to do something because…well, you can fill in the blanks. If you aren’t comfortable, or you feel something’s off, you have the right to step back and say, “No.” It’s the most liberating feeling ever!

Even better, for people like me who demand nothing less than perfection for themselves, freelancing grants you to outlet you always wanted. Clients WANT the best, and they respond to the exacting standards you set for yourself. I have a 100% satisfaction rating on Upwork (one of the job platforms for freelancers). I’m damn proud of that rating, too. I’ve rejected job offers that prioritized quantity over quality. I don’t compromise my standards, and I can do that because I’M THE BOSS!

3. NO Co-Workers

Okay, that may be a slight exaggeration. After all, I have Assistants that wander into the office and interrupt my work every day. However, they’e not on the payroll.

However, in general, those obnoxious people you want to throttle on a daily basis? Yeah, they don’t exist! People who get away with breaking rules that you get slammed for, people who sit around on their ass all day while you get sniped at for breathing for 5 minutes, and people who lie through their teeth to get out of work? Not here! It’s just you, baby! You can stretch out and breathe in the freedom of not having to deal with those irritations ever again.

This goes in conjunction with being your own boss. You don’t have to deal with the inequality inherent in the workplace. While a client may employ more than one freelancer, odds are you won’t interact with them or even speak with them. (You may never even know who they are) Even if you exchange messages, they don’t share your workspace. You can always let messages pile up while you work and answer them when you’re finished. (The equivalent of a “mute” button you wish existed in the real world)

4. 9 to Whatever

Freelancers create their own schedule. Yes, you have to meet deadlines set by your clients. You negotiate a lot of those deadlines in the first place, though. (And, most of the time, they’re a day and not a time) As far as WHEN the work happens, that’s up to you. Want to work through the wee hours of the night? Go for it! Want to stick to standard daylight hours to match a family member? No problem. Want to skip a day? No one’s going to say anything (provided you hand work assignments in on time).

You’re in control of YOURSELF. (I know, it sounds crazy, right? Almost like you’re an adult) I don’t work weekends. I save those days for family. Obviously, holidays are hit or miss (since I am working today – but I did my research ahead of time to minimize my working hours), but you can make a decision not to work holidays, if you choose. I’ll take the week of the wedding off, which means working my ass off right up to that point.

It’s a freedom you can’t find out of the freelance world. But it makes my life a MILLION times easier. I can schedule appointments whenever and work around them. I don’t have to go grovel to a manager and face an annoyed or disappointed look because *gasp* I needed to see the doctor. I don’t have to apologize to a frazzled receptionist when I have to beg for a weird appointment time to avoid inconveniencing my job. It’s one less stress in my life.

5. Personality’s a Plus

Does your regular job hand you binders of precisely how you’re supposed to behave? Do you get scripts of recitations to make sure everyone speaks and behaves exactly the same? You’re such good little sheep. Freelancers don’t have that problem. In fact, clients seek out freelancers precisely for their individual personalities! Ditch the uniformity and find your voice!

I get templates for some of my work. Clients want specific formats for the blog articles they request. Which I don’t mind, because I understand the look they’re adhering to. But within that framework, the voice and writing style are mine. It’s what the clients liked in my proposal (or the writing samples they clicked on in my profile). If they wanted a different voice, they would have hired someone else. Instead, they picked out my little quirky voice from the pack.

Instead of focusing on trying to follow the pack, you get to stand out. You WANT to stand out. Find your voice and make it sing. Figure out what makes your writing (or other freelance work) unique and play it up. The humor and geek culture references I always slipped into my narratives in other jobs (and caught flack for) are what earn me clients and five-star reviews now. You have an element of your personality destined to shine, and freelancing will turn it into a diamond.

Fly Your Freak Flag

Drone jobs suck the life out of you. I know – I’ve been there. Now I work my dream job, the job I assumed was always out of reach and impossible. It took NOTHING more than having the confidence to step up and say, “I want it.” It sounds insane, but it was that simple.

If your dream involves a freelance opportunity, then start exploring your options. You won’t regret it. Languishing in a job you hate – you’ll regret that forever.