This past month I’ve made contact with a few writers/prospective writers. They’re way smarter than me (not a difficult task) but still stuck in the “wish I could write for a living” stage. From my experiences at conferences, they’re not alone.

The biggest, hardest question most ask is about how to get started. It’s easy for me to make a living at this point — I have a bank of clients, a good reputation and a solid portfolio. If you’re just getting started, maybe these steps will help. Continue reading →

I don’t have to tell any of you what Orange is the New Black is. (If I do, go do some research. I’ll wait.)

The first season was interesting. I watched the fuck out of it in two binge sessions, in part over respect for the book, in part for Captain Janeway, in part for the objective quality of the story and production.

But then it started to suck. And why it sucks is an important thing for writers to learn from.

Thing is, as the second and third (and fourth) seasons developed, they gave us insights into the backgrounds and lives of the (at least from the perspective of the first season) secondary characters. This wasn’t a bad idea exactly, but the execution was a problem.

I’ve seen this problem before. I might have mentioned once or twice how I’m an avid player of role-playing games like Dungeons and Dragons and GURPS. For those who don’t know, those games often simulate combat. Some folks say they want those rules to be as realistic as possible. I disagree, because “roll to see if you pee yourself” isn’t fun for anybody. The rules should instead create an entertaining illusion.

Too much realism makes entertainment not entertaining.

In the case of Orange is the New Black, they overcorrected toward realism with the stories of those secondary characters. Occasionally interesting and relatable people end up in prison. Most of the time, though, inmates tend to be kind of stupid, kind of mean, and really boring.

Which describes all of the characters we’ve been exploring in the subsequent seasons of Orange. They made the characters too damn realistic. They made them like (unusually attractive) inmates. Stupid. Mean. Boring.

Not folks I’m going to relate to. Not folks I’m likely to root for.

Rory Miller, a man I deeply respect and actively like, wrote Violence: A Writer’s Guide. It’s a solid work on some of the realities of violence, and important for people who think they know violence to understand. It dives deep into the yucky of that world, and does provide excellent insight into the psychology of violence and of violence professionals. A writer who wants to write the motivations of criminals and cops well should read this book.

On the other hand, his advice on how to write violent scenes makes the same mistake. Realistically written violence isn’t entertaining. Writing violence well consists of myriad small skills, very few of which are related to writing a realistic scene.

Which brings me back to Orange.

The stories they tell touch on some important social issues, in a highly visible way that might actually change some minds or at least raise awareness. And if that’s their plan, then the realistic portrayals of these unfortunates might be exactly what’s called for.

But as writers, our job is to entertain. Even if we’re making a point. Entertaining stories grab more readers. Convert more thoughts. Engage more people. Don’t make the mistake of making realism more important than entertainment.

For almost all of us, there comes a time when we end up on the treadmill. The gerbil wheel. The Sisyphean slope. That point in our lives where we are working hard, fully engaged and in motion, but not actually going anywhere.

Are you now (or have you ever been) frequently saying or thinking things like…

• This gig is a dead-end street
• I need a change but I don’t know what, or how
• There’s no room for promotion here
• I’d be doing great if I just had X more bucks or Y more hours each month
• Fuck six blue ducks, but I hate my life

The treadmill is often frustrating, rarely rewarding, energy-consuming and more boring than Ben Stein at a stranger’s wedding telling you about this crazy dream he had. But – and here’s the insidious evil of the treadmill – it has just enough advantages to keep you on it.

You’re getting some exercise. We use regular treadmills because they let us run or walk to get healthier. The repetition of most treadmill gigs means you’re getting practice at one skill or another, eating up those 10,000 hours towards mastery.

Routine is comforting…and we love to be comfortable. Even for adventurous types, doing the same predictable thing for the same predictable paycheck cuts our stress. For some people, this is even more important than being challenged or fulfilled.

You’re getting paid. A “goodnuff” job at a “goodnuff” wage is what a lot of people have to live with because they have broader responsibilities or narrower options. We enjoy eating food and sleeping indoors, and a treadmill gig can help us do that.

I spent two years on a treadmill called Demand Studios. This company made money via a combination of gaming Google’s search algorithms and not-quite-lying about their profits for an eventual IPO. The work was boring and the pay just a nudge above insulting by professional standards. I usually love my editors, even (especially) the ones who push me. But editors there would tell me things like “Bruce Lee isn’t relevant to ab workouts” or “This article is about the United States. Don’t write about New Mexico.”

It was a treadmill, but at the time we had just had a baby and The Artist Formerly Known As My Wife suffered health complications that took her out of the contribution equation for half of the first year. What I needed was a comforting, low-stress, low-effort, reliable gig that paid the bills. By the time she was able to work in and out of the house, I’d fallen into that soporific routine and stayed there even when I should have been growing myself as a coach, speaker and writer.

As I discovered, and I imagine most of you know, the treadmill has problems that come along with the things it does all right.

You don’t grow new skills. I got great at writing 500-word online articles, but I didn’t learn how to write longer pieces, or humor, or speeches or white papers. A treadmill gig at a call center builds patience and communication skills, but won’t move you closer to your dream of owning the world’s funniest T-shirt company.

They eat up just that much time so you don’t have the energy or opportunities to pursue other avenues. I made okay money at Demand Studios, but would have been better off spending some of that earning time building other assets. Ask anybody who works at Home Depot or waiting tables “just until that big break” how absolutely true this is.

Comforable is just an inch away from complacent. Treadmills become ruts really fast. If you stay on one long enough, you find the habits and skills that help you get off of them have atrophied. You become addicted to the comfort, safety and routine. I stayed with that content mill for a year after I needed it, and everybody who’s ever waited tables knows that one 60-year-old who never got around to doing something else.

What if the treadmill breaks? “Steady jobs” are no more stable or dependable than freelance gigs. If your meal ticket stops paying out, you are screwed. When Google bitch-slapped Demand Studios, the whole thing came falling down. I was lucky to have found some other, better clients or I might be working a real job right no. When the mill closes down, this is exactly what happens.

If you want to be the person you wish you were, you must get off the treadmill.

“Please, do as they say! Get off the…treadmill!”

Treadmills give you just enough reward and give an illusion of reduced risk to stay tempting even when you know you should get off. But you want to get off, or you wouldn’t still be reading this.

In his landmark book The E-Myth, Michael Gerber identified the biggest problem entrepreneurs face:

People constitutionally suited for the daily grind and details of running a business aren’t the kind of people who are unhappy working in a regular job.

In my experience, this describes the overwhelming majority of folks looking for freelance writing jobs. They own that dislike of daily drudgery and details, and combine it with an artist’s approach to the work itself.

According to editors and clients I’ve worked with, this means working with a typical freelance writer means the following:

• Poor communication
• Missed deadlines
• Tantrums at editorial suggestions
• Inappropriate behavior on site
• Dropped assignments
• Unreliable scheduling

If you want to to make real money in your freelance writing job, don’t do this. Communicate regularly and honestly. Meet deadlines with the ruthless efficiency of a Terminator. Take feedback professionally, and remember that your client’s office is not the desk you set up in your spare room. Do what you say you will do without fail.

I’m not saying I’m constitutionally suited for this. If I were, I’d be turning in reports at a stable job somewhere. But I do have systems in place to keep me on track. I have the same challenge finding new clients that everybody else does…but when my clients need more work, I’m who they call.

How about you? What are the challenges you face when it comes to professionalism in your writing career? What systems do you use to overcome those challenges?

In my book The 9 Habits of Highly Profitable Writing, one of the habits I list is “Write Lots.”

When I first thought about writing professionally, I had the problem of underestimating the scale of available work. Now that I’m in my 6th year of writing full time, I have a better grasp on just how much work — and how many different kinds of work — is available for writers willing to chase it.

And you have to be willing to chase it. It’s not like it will be coming to you.

(Well, after a while it will start coming your way…but only after several years of doing the hunting yourself)

In the past six months, I’ve gotten paid to do the following kinds of writing:

• Ghostwriting on religion
• Web content
• Print magazine articles
• Travel & food writing
• Advertising copy
• Martial arts instructions
• Social media profiles
• E-books on writing
• Ghostwriting on international business
• Presentation scripts
• Game rules
• White papers
• Young adult fiction

In the same time, people I know in the industry have been paid to do the following other kinds of writing:

• Catalog text
• Calendar color commentary
• Travel guides
• Movie and TV scripts
• Research summaries
• Grant proposals
• Business plans
• Nonfiction books
• Fiction books
• Short stories
• Brochure copy
• Flyers for businesses
• Corporate employee manuals
• Social media engagement

The bottom line is this. It doesn’t matter what you want to write. You can find somebody willing to pay you to write it.

Go find that somebody.

Get paid.