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What Is Frustrating You About Your Freelance Writing Career?

This post is going to be short and sweet.

If you already read my blog post about my failing this past year, then you likely know that I this year is the year I want to up my blog and the content I’m creating.

Much of what I’ve written this year has to do with freelance writing, becoming a freelance writer, and overcoming some obstacles that naturally follow this path.

Next year, I want to be able to address this topic in a way that is the most helpful to you.

But I can’t really do that without your help.

A lot of what I’ve written thus far has to do with assumptions about what you’re struggling with.


Assumptions have a way of being wrong. 

So I want to ask you:

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What is your biggest struggle with being a freelance writer?


Is it pitching?

Finding better clients?

Breaking into a new market?

What has been your struggle?

I would love you to take a couple minutes out of your day to comment below and tell me.

My hope is that I can get a good idea of what you need me to create here on the blog so that I can help you further your writing business.

Don’t hesitate.

Pour your heart out and let me know!

Ari Rule

I'm Ari — a freelance writer, digital marketer, and side-hustle guinea pig. HustlePineapple is where you'll find my best tactics for freelance success, blogging and social media tips, and ideas for profitable side-hustles. Connect with me on Twitter or Instagram @HustlePineapple

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  1. Ariel, great question! My biggest struggle right now is finding quality clients who want reoccuring content. I’ve done several projects for clients that have paid well, but they’ve all been one-off type assignments.

    1. Thanks for taking the time to comment, Lisa :). I know this struggle all to well as I had the same issue when I was starting out. I’m actually working on a post that addresses this 😉

  2. Cruz Santana

    First off, I loved this post! You can tell you care about what you do and about your colleagues!

    Secondly, my biggest challenge is still finding enough paying work. I’m pitching like crazy, but I don’t see enough momentum going. I guess the short answer is I need speedy, steady work. Hope this helps

    1. My readers are the best! LOL seriously though, love them all :). May I ask, how long you’ve been at the writing game?

      1. Cruz Santana

        Well, I’ve worked as a ghostwriter since 2007. In November, I began to transition to writing web content after taking Gina’s course, 30 DOL. I blogged my way through it in a project I called, My Sweet November. That gave me a Kickstart into this business. I absolutely love it!

      2. Cruz Santana

        What about you? How long have you been doing this?

  3. Audra Rogers

    I completely agree about finding good, recurring clients. I’m also wrestling a bit with fear. I know this is the work I’m designed to do and I really love it. But I sometimes fear success just as much as failure. If something fails, you can go back to your comfort zone if things don’t work out. But if you succeed, things change and you have to be wise in your handling of it. It’s new territory for me. It’s a good problem to have though, and I’m looking forward to having it! 🙂

  4. Hi Ariel

    I’m just commenting in response to your call to action on Freelance Bloggers.

    My problem has been precisely the opposite of what others are saying.

    I’ve been far too reliant on regular work from a small number of clients. The problem with this is that I have a far too small client base. This can make it hard for me to raise my prices, as I could potentially lose a large chunk of work.

    Having lots of work from a limited number of clients also means I have little time for marketing. And once the regular work from a client dries up then I’m left financially exposed.

    Another problem is the quality of leads I get from my website. Far too many are from time-wasters who only seem to compare writers on price. These days, however, I’m far better at recognising the early signs of a tyre-kicker.

  5. First, let me just say, I’m a new reader so if you’ve already covered the comments that I’m about to write about, I’m sorry. I do plan to check out other posts, though!

    Anyway, here’s my thoughts:

    Frankly, one of my biggest problems is saying “no” to clients. Over the last few months, I’ve been overbooking myself, which is leading me to work on weekends and part of holiday vacations. This is partly because this line of work can have dry spells where it one week or month may be hard to pay the bills, while other months are so busy you worry about meeting deadlines. The “hard to pay bills” months worries me, so I have a tendency to not turn down work when the work is there – which leads me to overbooking myself. Also, part of that is due to the fact that I have a hard time “turning off” work mode, if you know what I mean. I tend to have a problem with transitioning from work time to play/life time as my mind is almost always reeling and churning out ideas to advance my business or brainstorming things for my client’s work needs. Although, I’m not sure there’s really any advice anyone can offer that will help me break this habit, it is definitely one that I struggle with.

    Aside from that, this year I’ve decided to try to take my business in a different direction. As such, I need to focus more on marketing my new website and services. That said, I’m brainstorming marketing ideas, other than simply guest posts. I have a few ideas that I plan to start working on this year, but I would love to hear what other freelance writers are doing to market their skills!

  6. Great question, Ariel. I struggle with a few things. The main one is patience, I suppose. I want success like six years ago! A big decision for me was to change my focus from spending hours a day on Craigslist and job boards searching for clients–only to have them love my pitch but not have the budget to pay what my time is worth, even though my fee is lower than it should be–to pitching to sound publications (HuffPo, Babble, The Penny Hoarder) to get my name out there, build my portfolio, and hopefully draw in better paying clients. I feel like this has been time better spent, yet there’s not much income now. It’s a lesson in patience,and I don’t like it. Ultimately, I’m hoping to secure a couple of great paying clients for recurring income from writing SOON. Thanks for the opportunity to share my struggle.

  7. Hi Ariel,

    Let me say first and foremost, I’m so glad I found your blog.

    I found you through Diana Marinova. She recently published a post on freelance blogs to follow and yours was one of them.

    Nice to meet you. 🙂

    Well, I can’t say I’m frustrated by a whole lot right now… things are going pretty well.

    Then again, the frustrations / challenges freelance writers face may be a little different than mine. I do some copywriting, but I mostly freelance as a social media manager.

    It’s not that I prefer social media management over writing… it’s that social media work is more conducive to monthly, recurring invoices.

    I’ve been freelancing full-time since 2014. Actually, I started blogging around the same time, but it was only this week that I relaunched and re-branded my blog to focus solely on helping other freelancers.

    I’ll be putting together an expert roundup of successful freelancers in the next couple months, and I’d love to have you participate.

    Hope you’re having an awesome day,


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