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Removing Freelance Roadblocks

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In a conversation with a fellow creative not long ago, I realized just how often we creatives put roadblocks up.

I greeted this creative, whom I’d met previously, and asked how things were going. Ten minutes later, I now knew more about how things weren’t going. And I was done. The conversation went something like this:

Me: Remember me? I met you at X a month ago!

Creative: I do! Yes!

Me: How are you?

Creative: Well, I’m still working out how to find materials that don’t cause my allergies to flare up …. (creative continues to talk in detail about these allergies and materials)

….. (five minutes pass)

….. (five more minutes pass)

I really like this particular creative person. I like the products they make. That made it all the harder to stand there listening to a story that this person had already told me the first time we’d met. And like this time, it was all about the things they can’t do.

Not once did I hear how this creative was actively trying to solve these issues. Well, beyond looking on the internet for different materials. I’d made a few sensible suggestions, as did my husband, but those suggestions were met with “I can’t” responses.

I felt like saying, “Correction: you can. You simply choose not to.”

Writers, how are we freelancers like this?

Putting on the I Can’t badge.

If the first instinct you have to someone’s suggestion is “I can’t” one of two things could be happening. Either the idea sucks and you really can’t do it, or you’re blocking. If someone says to you, “Here’s a letter of introduction for you to send to prospective clients” and you say, “But …” you’re blocking. You can do it. You simply won’t. Why? This is why:

Fearing failure.

I cannot tell you how many freelancers are terrified when they first start out. I was afraid, not going to lie. But when you fear failure to the extent that you do nothing, guess what? You’ve failed. So, why not just try? If someone rejects you, so what? Try again.

Lacking consistency.

That’s another one, actually. If you get rejected — correction, if your idea gets rejected, do you try again? Do you try consistently to find clients? Or do you say, “I tried that. Didn’t work” after one pass. Unless you tried it consistently for three months, you can’t say it didn’t work. And hey, if it’s been three months and you’re still without clients, look at that letter, look at who you’re targeting, and examine why it’s not working. Quitting is failure.

Making excuses.

“Freelancing is dead” and other pronouncements of how “bad” things are for creatives are no more than excuses for not getting off your butt and putting in the work. I’ve had so many writers over the decades argue with me that there’s no way that anyone can make a living freelance writing and each time I hear it, I come to an instant conclusion — these are people who haven’t put the work into it. And it is work. You have to find clients, win them over, do the work, and please them all while growing a freelance business. I’m here to say you can do it. There’s no reason why I can and you can’t.

Not one of these roadblocks is insurmountable. It takes a change in your perspective and a change in your level of commitment.

Your turn.

Veteran writers, what was your worst roadblock when you were first starting out?

Newer writers, what one thing do you think you need to get on the right path? We’re here to help.

 

 

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Category: Finding freelance work, Uncategorized

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2 thoughts on “Removing Freelance Roadblocks”

  1. Paula Hendrickson says:
    October 1, 2025 at 4:17 pm

    This will automatically age me, but when I first started out the biggest roadblock was having to send every LOI or query via regular mail — each with a stamped, self-addressed envelope. Postage was a huge expense, especially when sending photo copied clips. So I learned to be selective in which prospects were worth the postage.

    Not long ago I had a lengthy chat with a semi-established freelancer. Only one client, and they were having issues with the editor there encouraging different writers to cover the same things, then publishing whichever one came in first. I pointed out that’s not a very professional client. The writer had a solid idea, so I suggested sending a query one an editor I know would at least consider it, and even if the editor couldn’t use it they would encourage the writer to send more ideas. You guessed it. The writer never queried the editor.

    It’s bad enough when beginners back out on contacting editors or clients they don’t know. But when someone offers an introduction and you still can’t be bothered to send in an idea, that’s just sad.

    1. lwidmer says:
      October 2, 2025 at 9:12 am

      Maybe we need to treat every potential contact as whether or not they’re worthy of the extra stamp, what do you think?

      Oh, I’d never compete like that with work. Treat me like a pro, not like a contestant. You were so smart to suggest they shop that elsewhere. It’s the lack of follow through that’s killing these writers’ careers. It’s a shame because it’s an easier fix than they’re willing to take.

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