4 Reasons Why You Suck at Freelance Writing (and How to Fix Them All)

It’s funny how random conversations get you thinking.

I reconnected with a friend on Facebook, and it brought back a conversation we’d had years ago. It’s when I knew if her fortunes were going to change, it would have to be accidental.

She is one who is always about to start the diet, about to apply for that job, about to join that dating service … she’s ready, she’ll say. It’s time for a change, she’ll assert.

Years later, guess what kind of conversation she’s still having with herself?

Yes, it’s with herself, for she’s convincing no one else — not ten years from the first time I heard her “it’s time” proclamation.

Her inertia doesn’t make her a bad person. No, her inertia makes her a stuck person.

And how many freelance writers fall into this same pattern? I can’t count on two hands how many I’ve known who are probably still stuck in the starting block, waiting for some sign to move forward.

Freelance writer, today is the day that starting pistol blasts in your ears. Today is the day you’re going to get a whopping dose of get-off-your-ass, tough love. Today, I’m here to kick your figurative ass into gear.

How am I going to do that? You’re sitting in front of a monitor and, unless I’m willing to knock on your door and boot you personally in the backside, you can just thumb your nose at me.

Or you could read on. If you do that, then I know you’re serious about this profession and are looking to make a living freelancing. A good living.

So if you’re still reading, here are the things you’re doing that are keeping you on that bottom rung. And because I’m not one to leave you there, I’m also including ways to get you up to that next rung. And the next.

You whine. I whine too, so I get it. It’s tough getting your feet under you when you start out. So whine away about that. But do NOT whine about not being able to find work when you’re not really looking, or you don’t know where to look and you won’t ask what to do. It’s like the dog sitting on a thorn bush who is too damn lazy to get up and end his own misery. You have the power to move out of whine mode and into something a little more useful — like action mode.
The fix: whine your head off in private. Give yourself ten minutes to bitch, moan, and feel sorry for yourself. Then jot down four ways to change the situation. It could be four places to look for work (though I prefer you spend the time researching prospective clients you want to contact), four articles you’ll read on how to locate better clients, two marketing blogs and two how-to blogs… for every ten minutes you spend whining, spend ten minutes planning a way out of that funk.

You block. I’m more than a little weary of helping people who won’t help themselves. If you ask me for advice or leads or anything else (don’t ask for “overflow work” — please — there’s no such thing), I’m okay if you consider it or contact the prospect or mull it over and decide it’s not for you. I’m not okay with “I can’t” statements or any of the myriad excuses I hear when I stick my neck out for you. If you ask for a gig with X, Y, and Z criteria and I deliver that, don’t find that one thread to pull on that makes it all unravel for you.
The fix: stomp down your fear. You’re blocking because you’re afraid of failure. Honey, if you’re not doing anything, that is failure. Trying is movement in the right direction. Look for your own work, and fake confidence as you write that first email or make that first phone call. Don’t lean on other writers for your next gig. They worked their asses off to find clients. If they can, you can. 

You don’t show up. If I refer you to a client or contact at your request, you damn well better paste on your most professional demeanor and actually make that call or contact that person in some way. Don’t sit back and wait for them to come to you — go to them, particularly if I’ve alerted them that you’re about to contact them, and especially if I’ve arranged your meeting. Your bailing means two people are now pissed at you, and I’m the one you need to worry about because the other one won’t bother with you again.
The fix: be much, much more active in your pursuit of relationships. Stop thinking of meetings and phone calls as times when you must sell yourself. Change the perspective — you’re building a relationship, picking the brain of someone with loads of experience, and making friends. Just have a conversation. Write down three or four questions. Pretend it’s an interview and you’re there to get answers. And whatever you do, show up. If you don’t, I will hunt you down.

You just sit there. Don’t be like the handful of people I’ve encountered who will ask a really good question and then keep asking it repeatedly over the course of a few years. Oh, they’ll rephrase it just slightly, but it’s the same question. One writer was seen asking the same damn question five years later. Do they not like the advice? They said they did, but I don’t know for sure if they’re being honest or just placating. One thing I do know — they’re sure as hell not trying to locate the answer themselves. Even with it handed to them for free, they’re still sitting on their backsides doing nothing to change their fortunes.
The fix: get more curious. First, ask better questions –“How do I start freelance writing” is so broad a question that people have written scores of books to answer it. Instead, ask about one aspect. Second, if you don’t like what you’re hearing, don’t go ahead and take the advice anyway. That’s not going to do you any good. Instead, toss out the “what do you think if I would do…” follow-ups. And be much, much more like Joy Drohan, who wanted to boost her freelance career and put action behind it. She’s kicking serious butt just by putting a plan in place and working on it every week.

Writers, what excuses do you hear from writers that are keeping them in limbo?
What advice do you have for the freelancers who can’t seem to move beyond first gear?