8 Ways to Know You’ll Fail at Freelance Writing

What’s on the iPod: Better Together by Jack Johnson

We started the week with no air conditioning and temperatures that went over 90 degrees (F). Luckily, what we’d thought was cause for a new central air unit turned out to be just a disconnected wire. How it became disconnected is anyone’s guess, but it was under $100 to fix. That’s my favorite kind of problem.

So I spent Tuesday in relative comfort. To be honest, Monday wasn’t bad. I focused on work, kept my movements to a minimum, and the AC repair man had it all fixed before 3 pm, when things are usually hottest. Through it all, I worked. That’s because this is a job.

Despite a common misconception of what freelance writing careers are like, it’s work. It’s not hanging out in coffee shops with other writers discussing one’s latest Great American Novel. It’s not writing one book and thinking the work is done. It’s not deciding one day to become a freelance writer and then finding oneself inundated by offers and accolades.

If you didn’t get it the first time, I’ll say it again: running a freelance writing business is work, and plenty of it.

So it pains me to see articles, forum comments, and online chatter that pronounces some segment (or in some cases, all of freelance writing) dead or dying. It’s not only misleading to beginning freelancers; it’s utter bullshit.

Yes, there are cases in which freelancers don’t make it. It’s sad when it happens, but as I learned in a business course once, you don’t fail: you make a good business decision. If that decision is to hang it up, there should be plenty of thought and analysis that precedes the decision. It should be the same when you go into the freelance business, but we creatives tend to lead with our emotions. That’s fine. What isn’t fine is when we fail to back it up with hard work and learning.

There are ways to tell now if you’ll fail as a freelance writer. It’s in what you say and how you treat your business. Here are some of the habits I’ve observed among the barely-making-it and the scraping-by crowd:

I hate marketing. Welcome to the club. We all hate it when we first realize that people who hire us or buy our books don’t know we’re there. We have to tell them and convince them we know what we’re doing. That’s called marketing. There are plenty of ways to go about marketing in ways that are actually pleasant, so this excuse is lame.

I’d rather write books than market. And when you do, guess what? You still have to market. You have to find a publisher/publishing option, have a platform, grow your audience, and in a lot of cases, stump your book on book tours.

I just want to write. Then buy a journal. Honestly, you cannot do this job on just writing alone. You are starting a freelance writing business, and as such, you have to learn how to run that business. Writing is a large part of it, but so is invoicing, marketing, networking, accounting, etc.

I want to create it and let the income carry me into retirement. Good luck. That happens to .0001 percent of the writing population. The rest of us create a successful existence by continuing with and improving on our business practices.

Freelancing is dead. I used to get really upset when I saw this pronouncement; now I laugh and think “one more person who isn’t willing to put the work into it.” Freelancing is not dead, nor is it on life support. Freelance writing is a lucrative, satisfying career that offers constant challenges and allows you to define your own path, your own destiny.

I can’t make a decent living at it. Then raise your rates and learn how other freelancers do it. Follow the example of those successful freelancers who are actually freelancing, and who are working in areas that interest you. Build a process into your workweek that includes time every day to market (doesn’t have to consume your day, but rather take just a little time to connect/reconnect with clients), write for clients, and write for yourself. Oh, and stop working for free. You never get anywhere with that business model.

The work just isn’t there. That’s because you’re expecting the work to come to you, aren’t you? Passively cruising job boards or waiting for former clients to call means you’re going to sit without work. Instead, you should be searching, proactively, for clients you’d like to work with. It’s easy– do some research on those companies, locate the person who’s most likely to hire you, and send them an introductory letter that shows them how you can rock their world with your writing.

Clients are crazy and demanding. Then stop looking in the basement. Go upstairs and connect proactively with clients who value you and who won’t mind paying a better price for your skills.

Writers, how do you know the writer you’ve encountered is going to fail?

About the author




  • Eileen July 9, 2014 at 11:58 am

    I see this with women wanna-be freelancers: they let themselves be pulled in a dozen different directions on the homefront. Stay-at-home moms who see freelancing as a way to make an income … but then don't set any boundaries on their time or space. When you're a SAHM, everyone wants to claim a piece of your time–to be the room mom at school, to oversee the church bazaar, to watch their kids every Wednesday as a favor. I've seen several moms, who dreamed of a freelance career (and would have been really good at it), cave in and let others fill their calendar and chart their destiny. When they use language like, "I have to help in the church office on Tuesdays" (instead of "I want to help in the church office on Tuesdays, so I'll need to create my business to accommodate that") it's a dead giveaway that they are not in the driver's seat and will fail at this business.

  • Cathy Miller July 9, 2014 at 12:01 pm

    The writer who does not deal with the business side is in trouble. You have to deal with the business side.

    Even if you outsourced every bit of it (which is tough to do if you have no income coming in), you cannot ignore the business side. It's like not opening your bills because you don't want to deal with them. That doesn't make them go away. In fact, it makes the situation worse.

  • Lori Widmer July 9, 2014 at 1:29 pm

    Eileen, great example. People tend to create their own roadblocks, and then blame freelancing for their failure to act. It's women, but it's men, too. I remember one guy going on about how no one can make money freelancing anymore. When I pressed him about how that wasn't true and how he could change things, he said, "Well, I just dabble."

    You can probably guess what I wanted to say to him.

    Cathy, absolutely true. And that's a super way to put it — not opening your bills because you don't want to deal with them. We'd never do that, so why is it okay when it involves our earning potential?

  • Anne Wayman July 9, 2014 at 1:56 pm

    Can't say it better than Eileen, Cathy and of course, Lori!

  • Jennifer Mattern July 9, 2014 at 2:46 pm

    While I suspect I know what article inspired this, the funny thing is I could point out a few more just from going through my feed reader this morning. It made for painful reading today.

    One that jumped out was a post from a prominent indie author. They were explaining the path to indie publishing success, and basically it came down to not thinking of yourself as being in business until you're already an established author. No.

    I was so upset to see that, because it's going to hold some readers back when they hang on your every word and you say things like that. I'm glad they were able to succeed without that basic business understanding and planning up front. But the vast majority of authors will not. They can significantly improve their chances by realizing they're in business from the beginning, and by acting like it.

    That means embracing marketing and getting over your "I just want to write" dreams. If that's what you want, get a full-time job writing for someone else. It's not going to happen if you want to succeed independently. It is never a smart business decision to assume you're going to be the exception to the rule. If you are, that's great. But you can't count on it.

    It also means setting goals and working toward them without making excuses left and right about why you aren't succeeding. If you aren't reaching your goals, that's on you — not the general state of freelancing, not on clients, and not on anyone else.

    This post is also a good lead-in to your recent one on being careful about where you get your career advice. If the people you idolize are telling you that you can succeed without any kind of marketing, that freelancing is dying so you should take another approach, or that you can sit back and watch the money flow in without continued work, they're talking out of their asses and you need to leave then behind.

    Writers would do much better by seeking business advice from people with real business backgrounds and not solely from other writers. While some writers have that background, most do not. And success in your own writing career doesn't necessarily qualify you to advise others on successfully building their own businesses.

    As someone who does come from a business background (with a specialty in marketing and PR), it frustrates the hell out of me. I regularly see authors give each other terrible marketing and PR advice, and they blindly listen to each other as though they're experts. So new authors waste time and pursue risky tactics that any real PR pro would have warned them away from, all because one colleague did it and didn't get caught or called out publicly. That's not good business. It's dumb luck.

    So thanks for posting this Lori. It's a reality check I think a lot of new writers need to take in.

  • Gabriella July 9, 2014 at 2:53 pm

    Very good stuff, Lori. Another reason you'll fail? Because you don't take it seriously in the sense of meeting deadlines. This isn't some artsy-fartsy career where you get to mull over every word and every paragraph until you get things juuuuuust right–deadline be damned.

    You've said it before, that one of the reasons you got momentum was that always–always–met deadlines. Me, too. Many editors have come to me saying another writer has "flaked out" on them. I'm the go-to person when there's a crunch that another, less reliable writer has created.

  • Paula July 9, 2014 at 3:19 pm

    I agree 100% with every comment above.

    But did any of you ever get the feeling some of those "experts" saying freelancing is dead or dying are really trying to push back the competition?

    Changes in the global economy have made freelancing a more viable option than ever – just look at how many companies are looking to cut overhead costs like benefits by increasing their use of freelancers. (And, well, yeah, some are trying to call in-house contract workers "freelancers" when they really aren't. But that's another story.)

    More to Lori's point: I've mentioned it before, a few years ago a friend's sister thought she might lose her job at the local library, but said she wasn't worried. "I'll just be a freelance writer, like Paula." Um…what? She's one of those people who thinks getting an A in high school English means she's a good writer. No. It means she knows the parts of speech and might be able to diagram a sentence. She had no experience, no specialties, no clips, no clients…..but she thought if I could do it she could. (Which I found incredibly insulting.) She also assumed she'd be making money before her unemployment checks ran out. Luckily, she wasn't laid off.

    I enjoy sending LOIs and queries because each one I send is filled with possibility. But I LOVE invoicing because that means money is on its way!

  • Jennifer Mattern July 9, 2014 at 4:29 pm

    I do sometimes get that feeling Paula. I've come across it first-hand. A few years back a freelancer came onto the scene. When we first "met" online they assumed I was a newbie. I made the mistake of asking them what it was like working for a certain publication because I'd wanted to pitch them. They immediately got defensive, and basically implied I wasn't worth what that publication paid. Shocked the hell out of me given that I already made twice that on my standard contracts! It was clear they just didn't want someone else querying the publication, not that it would have had any effect on them given that we covered different topics. I didn't even bother correcting them. And later on they had the nerve to come to my own blog and leave a comment again implying I couldn't earn as much as them. I corrected them that time and never heard another word about it. But it really pissed me off at the time. This same person now tells new writers not to do certain things or take on certain types of work while they do it themselves. It's ridiculous that their readers don't pay enough attention to notice. But it's exactly what you're talking about. They don't care so much about helping their readers; it's more about pushing others away from being direct competition. And it's silly.

    You're also right about the economy. It's an amazing time to be a freelancer. There are a lot of opportunities for freelance growth when companies are cutting back. You just have to know how to appeal to those kinds of clients.

    I would have been insulted by that too! How crazy to just assume writing is easy and anyone can do it. Then again, those people often try and fail, and they're the ones I don't have much sympathy for because they don't take it seriously. Fortunately at least some of them learn the hard way and come back to the game better than before. As for the rest, well, I'm sure they have plenty of excuses to toss around.

  • Eileen July 9, 2014 at 6:00 pm

    This discussion brings to mind another indicator that a wanna-be is likely to fail: they don't want to do the legwork, but rather expect to have things handed to them. I may have shared this here a couple years ago, but it's such an off-the-wall story it's worth repeating. I had an aspiring copywriter seek me out who wanted to specialize in the same industry as me and was looking for advice. Fair enough; I was happy to send them some tips. They continued the email dialogue and I continued to answer out of courtesy, although after awhile I felt like I was being pumped for just a little too much information. Finally, they emailed me and asked if — get this — I would be willing to share my prospect mailing list! Umm … no. That's my most treasured asset, and a product of over 100 hours of work on my part. Why would I just willy nilly give that away? I don't think this person ever achieved much success as a freelancer.

  • Paula July 9, 2014 at 9:26 pm

    I think I might know who you're talking about, Jenn. There's one "guru" who spends so much bragging about how much they earn they probably have no time to actually write.

    Eileen, that sounds like people who expect you to refer them to your top clients! I've had that happen a couple times, total strangers wanting an "in" at a certain place. I just told them how I went about it – I researched, found a contact, mailed them a clip packet. Within a week I had my first assignment. But there's no way I'd play intermediary. (But now and then if I see someone I know writes well and has done the legwork but can't find the right contact, I'll gladly point them in the right direction.)

  • Jennifer Mattern July 10, 2014 at 12:03 am

    I've known more than a few who could fall into that group Paula. Thankfully most don't stick around for more than a few years before they either fail on their own or people catch on and stop paying attention to them.

    Eileen — That's crazy. It's one thing to ask a colleague what a publication's editor is like to work with before querying them. But it's something else entirely to ask for all of your contacts.

    In one of my worst experiences, I had a copycat colleague. They were new, and they decided they would build their career by mirroring mine (and those of a couple of other colleagues). It was bad enough when they mimicked my branding and stole some of the copy from my professional site. But then I found out they were trying to poach my clients in a completely underhanded way (and thankfully clients let me know). They didn't ask for my contact list. Instead they browsed my portfolio and contacted clients they found there. When they pitched my clients, they had the nerve to tell the clients I referred them.

    Lazy as all heck. And you're right. When they think they can succeed by riding someone else's coattails, it's a sure sign they'll never make it on their own.

  • Lori Widmer July 10, 2014 at 1:37 pm

    Jenn, you know exactly the article I'm referring to. To save the author any embarrassment, I won't reveal who it is. What absolutely blew me away about the piece, which described how she'd failed at freelancing (after just three years) was that this person was selling a book on how to succeed at freelancing. Huh?

    I see why that upset you. The minute you decide to write a book — hell, even when you're still forming the idea — you're in business. What lousy advice to treat it like anything else!

    Gabriella, another reason people fail, for sure. I remember a woman I'd been friends with — really like her, in fact. She'd asked me to hire her for a project. I did. I gave her a deadline. Three weeks AFTER the deadline, I finally caught up with her. "Yea, the subject was too hard (and it probably was), so I decided not to continue." Without telling me.

    You guessed it — she's no longer freelancing. Big surprise, huh?

    Paula, I remember that friend. I'm glad too that she stayed where she was!

    Like you and Jenn, I get that sense, but thankfully only occasionally. I've actually dragged people to work for the same places when they've needed more writers. Why not? It fosters good will and it helps increase your own value to the client (because you have connections).

    Eileen, I remember that story! It takes a lot of balls and a ton of stupidity to ask that of anyone. You're right — it's laziness a lot of times. This job is W-O-R-K, not play. It takes effort, and by gawd, if you're not willing to make that effort, give it up now.

    Jenn, I would have sent a note out to each of those clients explaining that you're not associated with that person and have not referred them. How awful! That one could have ruined your stellar reputation by screwing up.

  • Laureana August 4, 2014 at 4:32 pm

    I'm a freelance translator and loved your article.
    Every single word applies to my line of work.

  • Lori Widmer August 4, 2014 at 4:48 pm

    What do you translate, Laureana?

  • Laureana August 5, 2014 at 4:58 pm

    I'm a freelance technical translator working from English into Spanish.
    I truly appreciate your article because it resonates with what I do. I will take the liberty of sharing it among my colleagues, many of whom suffer from the 'victim mentality'.
    I've read several other entries and I am now a fan of your blog. Thanks for sharing your experience.

  • Lori Widmer August 5, 2014 at 5:22 pm

    Thanks for sharing it, Laureana! I appreciate it. And I'm glad you're now part of the blog community here. Hope you make it a habit. 🙂