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Earlier this month, the lovely and cynical John Hewitt’s post 10 Reasons Freelancing is for Suckers had me laughing for days, because it’s just so true. This morning, confirmation came via email.

Dear Amy,
I read through a lot of websites trying to find work from home schemes and i crossed through your website, Can you help me with that ?

I sat at the keyboard, tried to will my fingers into forming words. This shouldn’t have been such a daunting task. I get a lot of emails like this. And yet, I had nothing. There was nothing I could say to this guy that would be worth his time or mine.

The biggest lesson I’ve learned as a freelancer: most people don’t understand what I do.

This includes the multitude of friends and family members who think work-at-home means sits-around-watching-television. This includes the clients who like to see me as available exclusively to them 24/7. This includes the entrepreneurs who look down on me for selling a skill rather than a product. This includes the more-than-occasional naive websurfer who has heard The Great Promise about making money online and has maybe even read a copy of the latest “if you can write at a fifth grade level you can earn a living freelance writing” ebook.

If you’re new here and you’re scratching your head, let me whip out the mythbuster: freelancing isn’t easy. It takes skill, time, work. Above that, it takes a certain mentality. I like to call this mentality Survive Anything, but your experience may vary.

(Hey, I ragged on the suits, so you knew it was coming eventually…)

The Self-Employment:

Your taxes will be hell. Your health insurance will cost more than your car. You’ll be your own collection agent, your own publicist, your own marketing department. You will have to be your own boss, and you will also have many other bosses (they’re called clients).

The Juggling:

You’ll have to learn to juggle various projects for multiple clients at once. If you can’t learn how to do it — by prioritizing, making time for everything, even turning down work — you will get knocked out.

The Love/Hate:

Friends will envy you and hate you simultaneously. They will say “I wish I could work at home in my pajamas” and then — even though they have no skill — they will expect you to teach them. When you don’t, they will hate you.

The Drama:

The drama will come in many forms: flawed clients, dumbass potential clients, snot-flinging freelancers, your inner-jackass. Learn to let it roll off your back like a wet duck, or you’ll spend all day crying and breaking shit.

The Stress:

There will be days you want to jump off tall buildings.

The Rage:

There will be days you wish homicide was legal.

The Depression:

There will be days you wonder why you do this. The money problems, the mac & cheese, the madness of it all. Even if you’re a fabulous juggler, some days your skills will suck. You will hate yourself. You will hate the world. You will want to kill someone or jump off a tall building, but you won’t because you’re too depressed to have the energy.

Can you handle it?

I’m one of those freaks who obsesses over stupid shit. For example, getting the above picture to stay centered and not cause a text-break meltdown took a few days off my life. Does anyone but me care? Probably not. I obsess nonetheless.

Perfectionism: a lovely quality to some, a deadly shortcoming for others.

My clients love my attention to detail. They love that they can call me and say “I want the white thingy around my photo to be bigger,” and not only do I know what they mean, but it becomes a personal heart-mission. If I can’t fix it, it will drive me crazy. I will stay up all night and enlist the help of a small army of gurus if that’s what it takes to make the blog post not look like crap.

The trouble comes around 3 a.m., when I realize I’ve spent five hours obsessing about petty things — not just for my clients’ projects but for my own. Add 47 OCD “emergencies” to the roster, and I’m a day behind in jobs. I then become a procrastination whore on a mission to avoid my backlog at all cost. Caffeinated to the max, I sling my superhero cape aside and don a new costume: Idiot Girl.

Idiot Girl has no worries. She cares not that the Inbox spilleth over and that deadlines loometh. She is able to scale tall cities of blogs and message boards, and she has no censor button. She is wild and free. She leaves the grim prognosis of reality in her dust.

The next morning, all worlds crumble. Lost in the rubble of my own making, I ask myself Why? In the silence, a little voice whispers, “Take an hour off once in a while, and maybe you wouldn’t be such a moron.” (This isn’t a kind voice. She tells it like it is.)

So today, although I feel like I should be working, I am not. I will curl up in my warm cozy bed, turn the ringer off the phone, and ignore all emails that require any sort of thought process or action. I hope that tomorrow I will be more productive for it. And if not, I will blame schizophrenia.

Several months ago, one of my favorite clients began a conversation with a sentence I hate: “I’ve got a proposition for you.”

He asked me to come to his lovely faraway city to give a little talk to a small group of professionals about how blogging could help keep diarrhea germies out of kids’ dinner plates. Although I have plenty of blogging experience on the topic and have worked with enough lawyers and industry professionals to know the hows and whys of it, I really really REALLY did not want to do this.

I have an anxiety disorder and am about one step away from agoraphobic. I took up this lovely work at home life because I’m in love with pajamas. Phrases like corporate attire and business travel are supposed to be distant painful memories. Anyone but me would be thrilled at the opportunity. Networking, more business, great exposure. Yet the mere thought of getting on a plane and spending two days away from home gave me hives.

“I’ll do it,” I typed back… all the while thinking to myself, “I don’t know how I’ll do it, but I will.”

Then I got mono. And I quit smoking. I’m not quite as energetic as I was several months ago, and I’m certainly not very cheerful. While I’ve never backed out of a commitment to a client, I was very tempted many times over the past month to call my client up and open with another phrase I hate: “I regret to inform you…”

A few days ago I got an email from a lady whose little boy died from eating a hamburger. This woman lives in another country and has absolutely no connection to my client or this itty bitty conference. She simply shares the common thread of being the worst kind of victim to the issue I’m here to speak on today. Here is an excerpt from her letter, which I’m posting with her permission:

“… I have seen your passion for the need for better regulation within the United States and hope that your empathy extends to me globally. My son [name removed for confidentiality] died needlessly less than one year ago, and yet he is already nothing more than a statistic. To our government he has no name, but I hold his favorite teddy and weep and whisper my apologies into the air to whatever God may be listening. I could not protect my own child from death.”

This woman found me from a blog post I’d written. She’d read someplace that I do a lot of volunteer work and wanted to know if I would be willing to create a memorial website for her son and help her learn to blog so she could spread the word, in hopes that her son’s death would not be in vain.

As I got on the plane yesterday, I thought of this woman and her little boy. I thought about the many other little kids who go through painful kidney failure — many die — all because of the poison in our food supply coupled with careless meal preparation and bad hygiene habits. My panic attacks seemed small in comparison. If my little bit of knowledge about blogging can help keep even one kid off a dialysis machine, who am I not to want to sacrifice my pajamas?

In a few hours I give my little speech. But I realize now, this talk I’m giving probably isn’t the biggest reason I’m here. Last night at the hotel, half a dozen men gathered around me in their expensive suits and watched me write a blog post. My client said, “Watch her!” in a tone that connoted some sort of genius-level intelligence or superpower, simply because I could type into a little box and hit “publish” — and I had to laugh. Within a few hours, after making a call to a wizard-like blog developer, they were all up and running. The hotel lobby looked like a mini-geek convention, with “Hey, check this out!” being shouted across the room every few minutes, and everyone dashing over to watch with awe as a new photo was uploaded or a new hyperlink was created. That’s what this is all about. This is why I’m here — not just to talk about it, but to help it happen.

When the others bagged their laptops and went out for drinks, I stayed behind to catch up on my favorite blogs and to get some much needed sleep. As I was laying in bed, I thought about why we write, why we blog, why we do anything at all. Whether it’s to help someone else, to make a difference, to tame those insomniac muses of ours… I hope it’s for some bigger purpose than a paycheck. I’m a well-paid blogger, but I certainly don’t do it just for the money. Do you?

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Freelanceaholic: a word made up by a freelancer who works too much

Are you a workaholic freelancer who wants to recover? Now you can, in 10 easy steps! Alcoholics might need 12 steps, but we overachieving freelanceaholics can hack it in 10! I’ll even through in a free bonus!

(Disclaimer: the information below is intended for entertainment purposes only; I take no legal responsibility for your actions if you’re actually stupid enough to follow my advice and decide to sue me later. Thank you; please drive thru.)

1. Go to the nearest large body of water. Take your cell phone out of your pocket and throw. Watch out for fishermen.

2. Change the number to your home phone and don’t give it to anyone — ever. In fact, don’t memorize your new number; don’t even write it down. That way you won’t be able to give it out.

3. Change your email address and IM handle to something really girlish, like CatLovinGrrrl2007, even if you’ve got boy parts.

4. Make your signature line really awful. Something along the lines of “Honk if you still sleep with yo mama” usually works well.

5. Think up pet names for all your clients, like Butterball or Sugar Lickin’ Good, and address them as such.

6. If they seem turned on rather than appalled, try the same names out on their significant others. Make sure to call them at home, preferably in the middle of the night.

7. Still can’t shake ‘em? Stop using the letter E in anything you write. Once they get the first article titled T_n M_thods of Firing Los_r Cli_nts they should get the hint.

8. If they’re still begging you to work for them, start invoicing them multiple times per job. Set up an auto-responder to keep reminding them of their unpaid balances, even after they’ve already paid.

9. What do you mean they still love you? Ok, it’s time to break out the heavy artillery. Xerox a copy of your private parts (the hairier the better) and fax it to them marked URGENT.

10. If all else fails, cut your internet connection. Then drive an ax through your computer monitor and throw your hard drive into the fireplace.

Bonus Step: Sign up for Netflix. Play the movies while you’re working and write the cost off as a business expense.

You heard about freelancing and said, “I’ve got skills! I can do this!” Then you started doing it and thought, “Screw me! I’ve got to sell my services? Marketing, promotion, networking? Can’t I just slap my portfolio on the web and let the clients come to me?”

Well, no. So what can you do?

You can get bold and pitch new clients. Or, if that’s too salesman-like for you, you can make friends.

I’m not talking about meetcha-for-coffee, manicure buddies. I’m talking about online pals you can banter with, bounce ideas off of, and maybe — just maybe — score a little work from. The trick to this is to choose your friends, and your social activities, wisely. There’s only so much time in the day, and eventually you’ll have to devote some of that time to doing actual work.

Understand that what seems to work for a lot of folks won’t necessarily work for you.

For example: Twittering time away wouldn’t benefit me, because my potential clients still think Digg is something dogs do. Many of my clients seem to type with their feet, and a good many still don’t know what a blog is. Sure, I could maybe get an occasional lead or two from someone I meet on Twitter, but I know myself well enough to know that with my addictive personality, I’d mostly be talking to the pen men and Brett, and typing in stuff like “just had my 15th cup of coffee before noon.” These guys are super handy, and I’m glad to know them, but I don’t see them sending me any lawyer blogging business anytime soon. If these were the only people I talked to, I’d have a belly ache from laughing, but no new clients.

For me, the networking that works to get me business is visiting lawyer blogs, leaving comments, introducing myself via email. I’ve gotten more business through referrals from one legal blog I stalk than I have through any other method. Getting to know other writers who blog for lawyers, and who create lawyer blogs, is also handy.

You’ve got to figure out what would work for you. Who would make a good pal? Where would that kind of person hang out? Blogs? Message boards? Twitter? Digg? The local bar?

What have you tried and found useful? What did you find was a waste of time?

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  • About Amy Derby

    Formerly a corporate paralegal, I ditched the pantyhose to begin freelancing in 2004. I enjoy long walks to the coffee maker, never setting an alarm clock, and not wearing a bra to the (home) office. I can be reached at amy.derby (at) gmail.com.