The Freelance Creative

Ask a Freelancer: How Do You Get Over the Fear of Asking People for Work?

Nicole Dieker blogs endlessly about freelancing—in addition to freelancing quite a bit—and her audience responds to what she writes. She even breaks down how many pieces she writes and how much money she makes per week. That’s the type of transparency we’re looking for on The Freelancer.

From now on, Nicole will answer one question from an inquiring reader each week about the ins and outs of freelancing. Since there aren’t any manuals out there that tell you how to find the perfect balance of happiness and health insurance while working in your pajamas, we’re pleased to launch ‘Ask a Freelancer.’ Nicole, take it away…

How do you get over the fear of asking people for work? I know it’s probably just practice, but I really suffer from this, both with unsolicited calls for freelance work and from colleagues. Thanks!

– Sawyer Paul

Wait, an advice column? I can do this.

I can do this because I am afraid of nothing. At least when it comes to my freelance career.

How do I get over the fear of asking people for work? I ask a lot of people for a lot of work. I throw handfuls of spaghetti at the wall and see what sticks.

Of course, I do my research first. If there’s a publication that prefers macaroni to spaghetti, I get out my box of macaroni and start pitching. If an editor has a gluten allergy, I have to do the extra work to get the gluten-free box. When I pitch The Toast, I put the pasta back into the cupboard and throw slices of toast at the wall.

This is what I recommend for you as well. Do your research and then send out as many pitches as possible. Ask an online magazine to let you write a weekly advice column because you know you would be amazing at it. Send a note to an old client—”Hey, I just finished a big project for another client and wanted to check if you had any upcoming projects before I gave away my time to someone else.” You know, the note that totally doesn’t say I have no work, please give me work?

Just ask. Ask ask ask. Be smart about what to ask, but never stop asking.

Now for the other half of the question: the fear. The actual hitting send for the email or pressing call on the smartphone. (Whenever possible, always pick email. Nobody likes a cold call. Most people don’t even like warm calls.) When I was just getting started, I’d proofread the email, proofread again, hover my cursor over the “send” button, and go “ONE, TWO, THREE, SEND!”

And that was that.

It got easier over time, and I eventually got over my fear of hitting send, which is really a fear of rejection and/or making a huge, stupid mistake (dangling modifier, party of one?) that will make an editor want to erase you from existence. The only way to get over that fear is to pitch as much as possible and to keep making your pitches smarter and better until you learn to throw the right kind of al dente spaghetti against the wall.

Best of luck.

Have a question for Ask a Freelancer? Email Just count to three and hit send.

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