On Wednesday I was heading up to my gentleman friend’s house in northern Toronto. It was rush hour, and the office types were leaving the cool comfort of their air conditioned jobs and heading home. One girl sat down in front of me, dialed her BlackBerry, and began to cry.

She was having a miserable day at a miserable job that made her, well, miserable. Her manager was torturing her. She didn’t have clear instruction on what expectations she was supposed to meet. From the sounds of the conversation, she lacked leadership and was depserate.

Desperate.

Who hasn’t been there? Working in a job we hate, one that makes us unhappy sometimes to the point of sick, and yet trapped because we are afraid to take the leap to something else.

As I listened to her, I thought “There but for the grace of God go I.” My life without corporate employment hasn’t been easy. Of course, it was also plagued with the kind of marital strife that puts one in a shelter, and that certainly didn’t help. But regardless of these circumstances, and regardless of the nervousness that goes with striking out on your own, I could never imagine being once again trapped in corporate whoredom, listening to some overpaid MBA prattle on about things that don’t even matter.

Whoever that girl was on the bus, I hope she finds her path.

I had an interesting email exchange with a friend of mine yesterday. He was struggling with a client’s needs, and finally sent the client an email asking a very basic but very under-asked question:

How do you define the success of this project?

If you are a freelance writer, are you asking that question, and any necessary follow-ups, in order to fully understand your client’s vision?

If your client has you writing blog posts for their company, what are they hoping to achieve from your work?

• Increased sales
• Increased awareness
• Return readers

Many business people unfamiliar with the blogging world will check site statistics and think – “Hey, 1000 clicks, my writer is doing well!” or “Hmmm… only 100 hits. That writer isn’t worth the money.”

Better ways to look at it might be:

• Out of the 1000 hits, what percentage took the action you hoped for (a sale, a call, an email, a subscription)

If the writer delivered 100 clicks that resulted in 7 successes, or 1000 clicks that resulted in 4 successes, which is better?

Now, don’t you think it would be that much better if the writer had any clue as to how the client defined a successful website visit?

Writers are creative people, but we can’t read minds. If you are a freelance writer, you will have to pry the necessary information out of your clients, because they may not know that it is their responsibility to know these things. Many think that by just hiring a writer, the writer will know all the magical stuff about the client’s business.

Be sure to ask the question before signing the contract!

Beyond the client, you have to ask yourself how you define success. Is it by the amount of hours you have to work? The amount of money you make? The flexibility to meet other life demands? Once you know which questions to ask yourself, you’ll better know what to ask your freelance writing clients.

I read the Freelance Writing Jobs blogs every day. They get sent to my reader, so I don’t have to navigate the ever-growing list of blogs in the FWJ community, yet I still get all the great info.

Every few weeks, there’s a post from FWJ maven Deb Ng about how she’s against content mills as a whole, but how she gets slammed for having Demand Studios as a sponsor.

The truth is, I use a few content mills myself. I’m no stranger to word whoring.

What is a content mill?

So first off, what is a content mill? It’s generally a very low-paying place where you sign up and pick writing jobs like apples from a tree. You log in, there’s a list, and you pick what appeals to you from the list. Articles tend to be geared toward SEO marketing, though there are a few exceptions that actually require quality of content over quantity of keywords.

Which content mill to choose

I use three different ones: Textbroker, The Content Authority and Demand Studios. They each offer something different in terms of pay and type of articles.

The Content Authority is the proverbial $5 blowjob. Pay starts at half a penny per word. Articles are for SEO websites on different subjects, ranging from automobiles to making moonshine to getting your degree online. They tend to be short – rarely more than 450-500 words, and they don’t require a lot of effort or research to complete. FYI, Content Authority is currently understaffed and is offering bonuses to writers.

Textbroker pays a little bit more. You can make up to $20 per article, depending on the length. I’m a “Four Star” writer (it goes up to five), and I make about two cents a word. I know, rock the casbah!

Demand Studios is my favorite, as far as content sites go. You know where the article will be published, first of all. They tell you that right up front. It could be to eHow, or Livestrong or one of their other partner sites. Demand recently partnered with USA Today for some travel content. Articles start at $7.50 for simple 150-300 word jobs. Most of the articles I choose to write are $15 for about 400 words. Not hugely profitable, but at least I learn something while researching the articles.

So why do I even bother?

Well, every month, I set myself a monetary goal. That’s how much money I need to make from my various income sources – advertising, affiliate products, individual clients, etc. By the third week of the month, if I’m not on track, I kick into gear to make up the shortfall on the content sites. My sub-goal is to write less and less for the mills each month, and earn more through the other streams.

For example, at the start of 2010, approximately 35% of my income was from low-end mills like Textbroker (and bless them, it helped me pay off a surprise bill I hadn’t budgeted for). Now, about 20% of my income comes from Demand Studios. I hardly touch the other sites, though I’ve been paying a bit of attention to The Content Authority in the past week because of their desperation incentives.

Does this make me a loser?

Some freelancers turn up their noses, feeling that content mills are beneath them. Most of those freelancers have been in the business a while, and have a steady stream of income from other sources that they’ve built up over time. So yes, content mills are beneath them, just as one day they’ll be beneath me.

Whenever someone struggles to build their business, they will inevitably take some low-pay gigs along the way to top up the old bank account. Freelancers shouldn’t be ashamed to troll the mills once in a while. I’m not. I’m a proud word whore!

As readers well know, I celebrate No Pants Friday and Topless Wednesday. It’s the joy of working from home, and I know I’m not alone. Thousands of people with home offices work scantily clad or totally nekkid.

In fact, there’s a whole website for telecommuters called Working Naked.

And the woman who runs it, Lisa Kanarek, is having a contest: Where do you work naked?

I’m entering the contest because my home office has been stripped. It too is naked. Since the move, I have none of my belongings. No files, no notebooks – the 3-in-1 printer I was supposed to get in October vanished in a cloud of bullshit (my life is a very complicated story). Which means if I win any one of these prizes, I’m ahead of my own game:

Fellowes PS-79Ci Cross-Cut 100% Jam Proof Shredder
Epson WorkForce 610
Elfa products from The Container Store ($250 value)
Library edition binders from Russell + Hazel
Home Office Solutions: Creating a Space that Works for You book by Lisa Kanarek
One-year subscription to Flexjobs
Official “I’m working naked…are you?” t-shirt

I’ve gotta have that t-shirt, dammit. Anyway, grab your camera and get snapping.

Ugh. I fell ill last week. Really, really, hospital ill. And that sucks for me, but it also sucks for my clients. Being the sole proprietor of a freelance writing business means there’s no partner or secretary who can grab my address book while I’m being rushed away by ambulance, and give my clients a heads up.

So now I’m in a place where I’m feeling a little better, a little stronger, ready to work – and I have to apologize to my clients for dropping the ball. It’s awful. I feel terrible for letting people down – in some cases with time-sensitive work.

In addition to having to apologize, I need to implement a backup to make sure something like this can never happen again. A telephone tree, a Virtual Assistant – something to ensure that my clients will always have their work completed or at least regular updates as to my return.

I’m not sure how to implement this, but I’m certainly open to suggestions. Do I make a copy of my clients’ numbers for a friend? Do I get a MedicAlert bracelet made with “In case of unconsciousness, call clients!” written on it?

This is where I’d love to hear from other freealncers who work alone – whether it be in writing or some other medium. What do you have in place in case of emergency?

Sounds wonderful, doesn’t it? You make your own hours, set your goals, achieve them, and grab a martini to celebrate at the end of a short but satisfying day.

Or, you know, not.

The reality is that when you are entangled in an entrepreneurial life, there’s never a right time — for anything. There’s no right time, because there’s no time (and usually no money, either). For having kids, for buying a house, for getting a dog, for taking a vacation, for going out to dinner. Planning becomes difficult when income (if it exists at all) is insecure and savings are usually (to put it gently) unsubstantial. No matter how loudly private life calls out for investment — of time and of money — the business screams even louder in its demands for both. An entrepreneurial life becomes all about postponing — “When we break even…,” “When we get that contract…,” “When we hire that salesperson…” — ah, yes, that’s when our lives can move ahead.

When you are your own boss, you are the one in charge of figuring out where your next meal is coming from. There’s no handy drone in the HR department cutting your bi-weekly paycheck. You can’t make a budget in May and expect it to be valid in December, since half your clients will be scarce around Christmastime.

As a freelance writer, everything is feast or famine. There are months when I have too much to do that I end up outsourcing some of it. And other months where I am sitting on my hands, praying for work. Some clients pay on receipt of a job – others are Net 60. How do you plan around that?

Some people choose to put their lives on hold for a few years while they get set up. Others refuse to live like that. It really all depends on how thick your skin is and how much sleep you want to get.

As the author of the quoted article points out, some things can’t be put off. A woman can only put motherhood off for so long before that window closes forever. You can only put off saving for retirement for so long before you actually reach retirement age. Time doesn’t stop just because you’re trying to make your business profitable.

Many thanks to @missusP on Twitter for pointing this article out to me.

I’ve taken some time off from blogging, but not from reading. Every day I still open my Google reader and go through eleventy-trillion different nuggets of information.

I thought I’d share a few here with you:

• Office Hours Blog, which I write for, has great tips and tricks for social media, adding podcasts to your website and more
• Blogging Without a Blog has a post up about The Legal Side of Blogging – this’ll keep you honest
• AKA A Writer has a series on Entrepreneurial Marketing that is well worth a read
• Mary Jaksch has outdone herself in the list-making department with 176 Tips for Writers
• And last but never least, the brilliant Leo Balbuta is giving away FREE STUFF

So, what have you been doing with your summer vacation?

I’m a writer. I write. I don’t design websites, I don’t do flashy full-color brochures, I can barely remember my HTML basics. I write, and I podcast. That’s it.

So what do I do when I have clients asking if I can re-design their sales brochures or websites? Well, in an ideal world, I would be able to flip through my rolodex (no, of course I don’t have a real rolodex anymore – who does?) and say “Sure, call Josh! He’s a photographer/artist/printer/designer/whatever, and he’ll be able to help you.”

Except I don’t know a Josh (actually, I do know a Josh, but he’s a mechanic). I don’t have someone I can ask to help me provide turnkey serevices to a client.

Could you be my Josh? Let’s talk. Email me at sullivanwriting@gmail.com and tell me what you do for a living. Send me a link to your portfolio. Maybe we can help each other out.

I read this piece at All Freelance Writing and nearly wept with frustration and joy. At some point we’ve all said something like this, either on our blogs or to our freelance colleagues.

Don’t act like you’re hiring a full-time employee. - I’m shocked by how many people request formal resumes and such from potential freelancers. What’s worse though is that today I saw a company asking for things like cumulative GPAs. Folks, these traditional requests are fine if you’re hiring an employee. They’re often completely overboard when hiring someone for short-term per-project gigs. Instead look at their portfolios. Their work will speak for itself. (And frankly, there’s no reason you need someone’s GPA to hire them as a part-time, freelance blogger. That’s just silly and makes a bad impression – this particular advertiser came across as absurdly demanding for example with their list of requirements.)

I’ve seen ads like this. They’re so frustrating, because obviously some automaton in HR drafted the ad according to company hiring policy for employees, and no one has a clue how to hire a contractor. Ads for freelance writing gigs that ask you for transcripts or a list of every job you’ve ever had since McDonald’s when you were 15 are completely out of line (the exception being anything that requires a government security clearance, of course). You want to hire me as a writer, but want to know about when I mowed lawns in college? How does that apply in any way, shape or form to me writing your marketing copy?

And you want free custom samples? Are you on crack? Tell ya what: I’ll do for you what my tailor does for me. If I want something bespoke, I place a deposit that covers the cost of materials. Then if I return and hate the piece my tailor made for me, I lose the deposit. No hard feelings – we’re both covered. I don’t have to buy the piece, and he’s not out of pocket (this happened once with a pair of leather pants when I was a dominatrix – we moved on and continued our professional relationship). Seriously, do you go to a restaurant, eat a meal, then tell the waiter it was “just a sample” and you shouldn’t have to pay for it since you didn’t like it all that much? If I were the waiter you tried that on, I’d punch you in the stomach repeatedly till you vomited, thereby breaking you of a very bad habit of ripping off restaurants.

I’m so glad Jennifer wrote that piece. I think it should be sent to every person who places an unrealistic and ludicrous ad on Craigslist, looking to exploit freelance writers.

Even when it’s a hobby, it’s a business. If you love it and are passionate about it, you’re probably devoting hours to it every day. It’s as time consuming as (and way more satisfying than) golf.

Five years ago when I started mine, I had no idea that one day people would be paying me to blog. WTF? Seriously? Wow. It began with a few ads and paid posts. Hmmm… then people were contacting me to come write for them at their blogs. Some were even offering to pay me!

And I’m not the only one.

There are numerous ways to expand your client base and increase the size of your portfolio. Common tactics used to do this include utilizing your contacts, taking part in relevant discussion forums, being active in freelance marketplaces and even watching industry specific job boards.

One idea that is implemented by some people but certainly not by everyone, is blogging. Sharing your abilities with the world in the hope that the right person finds what you have to offer. Through my experience though, quite a few people fail to have any success when trying to use this strategy.

Today I want to share my own story, and how I made over $20,000 in 4 months when my only source of clients were through blogging.

Now in this article Glenn discusses how his blogging was a matter of marketing, and that’s how he drew clients. It’s a brilliant way of showing off your abilities both as a writer and as an expert in your field.  I get gigs writing about politics (especially in areas of terror and religion) because that’s my thing. If your area of expertise is pet care or life coaching, that’s where you’ll drum up business.

In addition, if you’re a good blogger, you will be asked to write blogs. Companies love adding them, but no one has the patience or ability to actually write the posts. Enter the freelance blogger. A 500 word blog post can earn you upwards of $20 (Actually, it could earn you $1 if that’s what you’re willing to take. Another time we’ll discuss the quality differences between an escort and a crack whore, but not today). Get a few gigs writing 3 or 4 posts each per week, and you have a nice little income. It’s a sweet deal, if you’re doing something you love.

I strongly suggest that anyone who wants to break into freelance writing or blogging for a living tries Ali Hale’s Staff Blogging Course. Do a read-through of the 8 modules, then go back and put the lessons into practice. I did, and have since scored TWO THREE blogging jobs in the last two weeks. Cost of the course: $19. Income of jobs I’ve scored: $125/wk. $180/wk.