Ask a Freelancer

10 Mistakes That’ll Ruin Your Freelancing Career

By Nicole Dieker August 25th, 2015

A while back, you asked for questions or concerns from experienced freelancers looking to make a move upwards. I’ve been an agricultural writer for 17 years and write for regional and national trade publications, primarily long features. I have, in the past, written for a few consumer publications, primarily agricultural or historical pieces on the local/regional level, but can’t seem to find my way back into these markets. What’s holding me back from moving my career to the next level?

—I’ve Got the Exp, Why Can’t I Level Up?

So you’ve got what it takes but you aren’t getting the gigs. That can be very frustrating. Let’s try to figure out if there’s an underlying problem here.

It’s a little hard to say why any individual freelancer isn’t moving up to the next level. I’m going to assume you aren’t making any of the obvious blunders like missing deadlines, turning in sloppy work, or arguing with your editors over every revision.

But there are plenty of less pronounced mistakes that could be torpedoing your progress:

1. You push boundaries

I get a lot of emails from freelancers I don’t know who ask me to either review their portfolio, tell them who’s hiring, or pass their name along to my editors. I regularly do that kind of work for freelancers I have relationships with—after all, recommendations and networking are a huge part of building a freelance career—but I won’t recommend the work of a writer who contacts me out of the blue. That’s at least a Level 3 relationship step, and I’m at Level 0 with people send me introductory emails.

When I pass along a writer’s name to an editor, I am vouching that this person has talent and is easy to work with. When someone cold-emails me asking for my contacts, what first comes to mind is that this person might be hard to work with.

2. You jump the hierarchy

If an editor doesn’t respond quickly enough (to your pitch, your draft, your revisions), don’t email the editor’s boss. As I’ve written before in this very column: “Going above someone to the boss will probably end the working relationship with the editor you’ve struggled with.”

Do your job, and let your editors do theirs. Sometimes it’ll take months to hear back, but—at least from my experience—articles nearly always get published if you’re patient and respectful.

3. Your emails are too long

If you can’t write a good email, you won’t get hired to write a good story. It’s probably a habit most of us could improve. Letter Writer, your original email to me was several paragraphs longer than the typical Ask a Freelancer question. That’s not to say your message wasn’t important, but when you’re trying to reach out to someone, the shorter, the better.

How long are your pitch emails? What about your emails when you respond to an editor’s request? Are you using paragraphs when you should use sentences? Keep things short and to the point, and give editors direct questions that can be answered quickly. A short email shows you understand the rules and structures of contemporary email communication, which suggests you understand other types of writing as well.

4. You don’t know what your story is

People often pitch topics instead of stories. “I want to write about money and relationships” is a topic. “I want to shadow a newly married couple for 24 hours and track all of their money decisions” is a story.

Also, you should actually have a newly married couple who has agreed to this hypothetical request. You don’t always need to secure your sources before you pitch, but if you’re getting that specific, it’s best to take care of the logistical reporting so you don’t have to go back with an excuse about why your story fell through.

5. You aren’t reading enough

Read everything. Read sites unrelated to your beat. Stay up to date on current events. Read the pop culture sites so you’ll know which references to make.

Reading shows you what other writers are doing and what other publications are publishing. It also helps you find new places to pitch—and ensures that you are already familiar with their work and their audience before you send your ideas.

6. You don’t comment on the sites you want to pitch

Editors pay attention. If you’re a commenter with a history of contributing to discussions on a site, they’ll probably recognize your name when you pitch and will be more likely to green-light your idea.

This isn’t to say that an active commenting presence automatically guarantees a byline. However, forming a relationship—even a small one—with a particular publication does help when it comes time to pitch. It’s worked for me.

7. You don’t have an active online presence

Twitter and Facebook accounts are important. Having a personal website helps. Growing your audience online shows editors that you know how to write for and interact with a community. It also gives them a look into your personality: Are you going to be a joy to work with or are you going to subtweet your editors after they ask you to change a “to be” verb?

So if you don’t have a Twitter account—and I didn’t see you list one on your website, Letter Writer—make one immediately. You’ll be able to follow writers and editors and form relationships that might lead to future gigs.

8. You aren’t tracking your business

What gets measured gets managed. The very act of writing down how much money you earn incentivizes you to find ways to earn more. Trust me on this one; I’ve been tracking my income publicly for more than three years.

Even now that I have a pretty stable client base, writing down what I’m earning lets me know when it’s time to make an adjustment. If you think you can keep it all in your head, you’re going to make mistakes.

9. You take rejection personally

Freelancing is like dating. Some people just aren’t going to be that into you. Spending too much time asking “Why not me?” will delay you from pitching the people who actually want you.

Keep reading, keep seeking out new clients, keep building your relationships with other writers and editors, and keep pitching. I’m glad that you asked me what’s holding you back, but now that you’ve read this answer, start asking yourself how to move forward.

10. You make excuses

Yes, it is harder to freelance with a part-time job. It is harder if your kids are at home while you work. It is harder if you struggle with procrastination. It’s harder if you are ill or injured.

It’s also harder if you compare freelancing to the “good old days,” when publications regularly paid $1 or $2 per word, while you’re trying to build a career on 25 cents a word. It’s easy to feel like the freelancing world is actively working against your success.

But if you constantly focus on limitations, you’ll get stuck. Find the parts of the job that you can do and fixate on those. Nobody can do everything. There are jobs I turn down because they don’t make sense with my life and schedule. Figure out what you can work with and make it work for you. That’s the only way you’ll get to the next level.

Nicole Dieker has leveled up many times during her freelance career, and she knows how easy it is to stare at your experience points and wonder why you aren’t moving up more quickly. Are you waiting for your next level boost? Send your Ask a Freelancer questions to

Image by Rob Byron
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