How to Be a Freelance Writing Failure (and how to change)

Typically, I don’t get frustrated when another writer asks for help.

But sometimes, the situation is far from typical.

In a recent exchange, the writer expressed a level of angst that was troubling. Nothing in this writer’s marketing was working. Things weren’t coming easy anymore. The work wasn’t paying off.

Been there. Haven’t you?

I feel for anyone who struggles in their freelance writing careers because it could just as easily be me. Or you. Or any of us depending on the factors involved and the level of commitment we still have to this gig.

What I don’t feel for is someone who insists in turning your advice into first a roadblock, then an insult.

Oh yes, that did happen.

Without revealing too much about the situation, plenty of other writers offered some pretty good suggestions. So did I. I let the writer know that yes, the frustration she was feeling was normal, but that I could see a few things she could change that might change her fortunes a bit. I offered a few suggestions.

The first set of reactions is one we working writers see commonly enough.

“I tried that, didn’t work.”

“I tried that, too. Didn’t work.”

“That never worked for me.”

“No, I don’t think the clients I’m targeting will respond to that.”

I know what you’re thinking — it’s the same thing I’m thinking: yes, she tried. But did she stick with it, or was it one of those play-at-it-for-a-few-days-and-drop-it attempts, or did she give it a few months, complete with follow-up?

I didn’t say anything more. When a freelance writer throws up several roadblocks at once, I’ve learned to stop running headlong into them. I disengaged.

A week later, someone else posted a similar experience, but hers was a bit more hopeful. I was about to answer when I saw the first writer’s response, which went like so:

Writers who aren’t struggling tend to think it’s because they’re doing something right and we who are struggling are at fault. It’s arrogance.

Enter the sound of me disengaging from this writer completely. It’s one thing to say every suggestion isn’t going to work for you. It’s another to blame your mood and your inertia on other people being arrogant.

I have a two-word response to that, but I’m trying to stay away from cursing. It rhymes with “duck cough.”

That response to all the help she was given — that’s a failure to see inside yourself.

That second response — that’s a failure to be anything but a self-righteous ass. (So much for my moratorium on cursing.)

Both actions are sending this writer farther down the path to failure. But that second one — that’s pretty much going to guarantee it’s a one-way trip. You can’t insult people who are helping you and expect that help to continue.

That’s a pretty big failure. Even if this writer turns it around, she’s lost the confidence — and the camaraderie — of a valuable community of writers. Foot, meet bullet.

Fortunately, most writers aren’t spoiling for a fight like that, nor are they prone to blaming their problems on everyone around them. Unfortunately, there are still more ways to screw yourself over and leave permanent marks:

Jump without a parachute.

No business plan, no marketing plan, no defined direction … welcome to failure. I have yet to find a freelancer who doesn’t have some sort of idea where they’re heading. I’m not talking all formalized plans and regimented schedules (unless that turns you on). I’m talking about knowing who your ideal client might be, what kinds of work you like better than others, how to reach these people, and how often to market to them (hint: every day). Yet there are still writers who start out with this small pool of clients — maybe old bosses, friends of friends, association members — and they get work easily.

Funny thing, though. Work dries up. People’s needs change. And that writer? That writer still doesn’t know how to market because he/she never had to.

How to fix it. Plan, but plan in a way that suits you. My formal business plan never did me an ounce of good. It was too long, too formal. I’ve never worked well when I’ve been expected to outline, so formal isn’t going to fit me. If your idea of a plan is a list of bullet points you tape to your monitor, go for it. If you like to have spreadsheets and you thrive in a command center-style environment, knock yourself out. Just find a way to make finding work and growing your freelance writing business easy for you.

Focus on the cash.

I wish I could say this particular writer was at least not focused on the money. Alas …. You can’t focus on money. If you do, you will fail. The client’s needs won’t be met, the money will stop flowing, and you’ll be as poor as you were before you started.

How to fix it. Focus on the client relationships. If you satisfy a client, they’ll come back. If you make great connections, they’ll refer you. If you make it about what they want and not about what you need, you’ll win a lot of trust and maybe even some loyalty.

Think you must starve for it to be art.

I know one writer who struggles to make rent every month. Yet when I suggested three other places she could easily be working, she said “No, I want to be just in this subject area.” Totally missed the point that she still would be, only with a few more markets at her disposal. Again, I disengage when logic becomes a non sequitur.

How to fix it. Lose the prima donna attitude. I create art every time I write something for someone. My art may be a ghostwritten article or a website page, but its no less creative than your carefully crafted blog post. You want to eat on occasion? Be hyper-choosy. You want to eat well? Stop poo-pooing actual work. Or get a job at a 9-to-5 and do the writing you want on the side. Just stop whining about being poor while turning down any opportunity to improve your fortunes.

Let your pride get in the way.

Pride is deadly in freelance writing. Ask the struggling writer who resorted to insults. It made me wonder how she took feedback from clients. The first lesson you learn is it isn’t about you — it’s about the clients and making them happy. But if you’re going to get pissed whenever they ask for revisions or don’t like what they see, you’re going to have a short-lived career.

How to fix it. Shift. Your. Perspective. Honey, it’s not about you until the check arrives, and only then it’s about a job well done. Pat  yourself on the back, then get back to work. You’re only as good as the service you provide. You can’t take revisions as personal attacks. You can’t think you know better than the person whose business you’re working with. Let them lead you toward what they want, and then give them exactly that. Don’t take direct insults, but don’t be insulted by every damn blip on the radar.

Writers, what failures have you seen? 
When you see another writer making fatal errors, how do you approach it?