Free Advice Friday: 4 Freelance Business Mistakes That Kill Your Career

What I’m listening to: Under Pressure by Queen & David Bowie

Wow. Friday already?

It went by a bit quickly. I have projects in the works, but until I get some interviews completed, I have some free time. I spent it working on two personal projects and trying to learn a new bit of Windows 10 functionality. No sense having technology if you don’t know how to use it, I say.

I had time too to visit some forums, answer some emails, and have conversations with writers of various career levels. It’s always refreshing to talk with successful freelancers — these are people anyone can and should learn from. I know I do.

See, they get it. They’ve figured out that being a freelance writer is so much more than merely writing for clients. The attention they give to their entire business shows in the results they get. There are no shortcuts, but plenty of work, research, and learning to make a successful business grow.

That’s why I was disturbed when I saw a course that promised to fast track writers into careers, skipping over the “unnecessary” stuff, and by interviewing successful writers and copying what they do. While I’m not exactly sure what these organizers consider to be unnecessary, there’s an undercurrent to that message that I just don’t like. It’s this: You too can just ride the coattails of those before you.

Can that method work? For a while, yes. And maybe that’s the point of this course — to jump-start flagging careers and give these freelancers something on which to build. But to skip over stuff? I don’t see that method sustaining any writer in the long term.

Yet there are freelance writers who need the guidance, particularly when it comes to running a business. They make mistakes — non-writing mistakes — that kill their chances before they get going. Here are some of the more recent issues I’ve encountered that can bring down your freelance writing business:

Using blanket queries. You know those form letters you get that you hate so much? Why would you think sending them to your prospective clients will net you any different reaction than your own? People do business with people. If all you’re doing is filling in a new name and email address, you’ve failed to understand how to really connect with your prospective clients.

Putting that blasé attitude front and center. Plenty of freelancers would be surprised by how their actions are interpreted by others. Little things can wave big flags — expecting your sources to contact you, missing deadlines, missing phone calls, making piss-poor excuses (any excuse is piss poor), not focusing on the task, putting other things in front of that thing you’re not doing, even not taking seriously your next conversation. Any one of these can raise a flag. Any two or more can have that client running the other way.

Forgetting the business side. If you began your freelance writing career thinking you’d be doing mostly writing, you’re going nowhere fast. You are a small business owner. You can’t dabble in writing if you intend to make a living at it. That means you have to run your business wisely. Act professionally with clients and colleagues, form connections, nurture client relationships, focus on pleasing them and not your wallet, and doing the damn legwork it takes to be successful.

Looking for shortcuts. Seriously, don’t you think if there were such a thing as a shortcut, we’d all have taken it by now? Here’s a fact about freelance writing that will not change: It takes hard work to create a successful freelance writing business. So suck it up, buttercup. Time to work your ass off.

Writers, what were some of your early business mistakes that you’ve overcome?
What other mistakes have you seen freelance writers make?
How would you advise a new writer who’s wanting to grow his or her career potential?

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  • Paula Hendrickson June 17, 2016 at 2:46 pm

    You covered most of the biggies, Lori. The thing is people who take short cuts to LAND the clients don't seem to realize that they'll also have to PLEASE any clients they land.

    And if potential clients can't tell generic form-letter queries from pitches tailored specifically for their eyes, you have to ask yourself if those are clients worth having. They probably also think 10-cents a word is a decent fee, want to buy all rights, pay within 3 months of publication, and won't be a clip worth saving.

    My advice is always to get a first clip from a respectable publication— which might not pay much since you got the assignment without having any clips to prove you can write—and use that clip to break into a larger market. Rinse and repeat. Don't write more than one or two pieces for a low payer. If you do, they're using you. You need to use THEM as a stepping stone to a better market.

  • Mistakes Writers Make June 17, 2016 at 5:12 pm

    I agree with Paula on not being exploited by low (or, worse, non-) payers, but I'd add that even if you do work for some low paying clients you should be sure to chase up those debts if they fail to pay punctually. In the early days, I was almost too grateful for an assignment, even if only for a two-figure sum, that I'd sometimes not be as forceful as I should have been to chase late payments.

    Writers need to realise that they're entering into a contract for a piece of work, and payment for that work signifies the 'completion' of that arrangement – you owe it to yourself, and to other writers, to make sure you are paid what you were told or arranged you would be paid. Even small sums are worth pursuing – they remind clients that writers have value and should be recompensed – period.

    Best wishes, Alex

    PS. I expect to be breaching your copyright on 'suck it up, buttercup' multiple times in future …. 🙂

  • Lori Widmer June 17, 2016 at 6:03 pm

    Paula, I think the flip side of the form letter is if you're using it, how are you showing your potential client that you can generate compelling, original content? And you're so right about using these markets for clips, not as places to hang out for years.

    Alex, LOL Isn't it great? Full disclosure, it's not my original thought. I saw it on a workout t-shirt and I loved it.

    Agree completely on chasing payment. Have a payment process in place that includes how often you'll invoice, how many times you'll invoice, what your late fees will be, and what steps you'll take should a client decide to ignore all those invoices. Then follow it.

  • Eileen June 17, 2016 at 8:46 pm

    My Big Early Mistake was in chasing after local, low-paying clients because I didn't have the confidence to go bigger. The problem was, they required too much hand-holding, too many time-sucking meetings, and too much educating about the benefits. They would want me to visit their place of business, take a tour of their entire operation, meet the owner and whoever was doing the marketing, meet Mabel at the front desk with a degree in English who had been doing their writing and who resented the hell out of me, and give them a strategy for free. And then they only wanted to pay $100 for web copy. I foolishly did that too many times before I got smart.

    I would advise new writers to pick a specialty or two, and target businesses in that market with the ability to pay. I found the sweet spot to be $20 million+ in annual revenues. If someone is looking at a generalist vs a specialist, they're going to choose the specialist.

  • Devon Ellington June 17, 2016 at 8:48 pm

    Yeah, I'm sick of the attitude, "Oh, I decided to start freelance writing. Easy money." Uh, no. It's work. It's often worth it, sometimes not, but there's definitely work involved.

  • Lori Widmer June 20, 2016 at 1:58 pm

    Oh gawd, Eileen! I've had those very same clients! LOL We should compare notes — I wonder if they're the same people. One client walked me through his offices, bragging about how much money he was raking in. When he heard my fee, he had the audacity to say "Ooo, you're going to have to lower that."

    My response was "You're going to have to raise yours to afford me." Needless to say, I didn't bother with him after that, nor did I volunteer to work for three days beside him to, as he put it "rub shoulders with people who can hire you!" I was too busy working for people who actually DID hire me. 🙂

    I wondered how your targeted marketing was going. Glad to hear that you've found a sweet spot!

    Devon, I think of you every time I have to write one of these posts. You get some of the crazies who expect you to do their damn legwork.