What I Learned from Talking to 60 Freelance Writers 

Note from Jennifer: I’m super excited about the Content Byte Summit 2023 in Sydney, Australia, which is happening September 14-16, 2023. I’ll be there in person as a keynote speaker, and there are loads of other content marketing experts on the docket so this is going to be a really valuable event with lots of opportunities to learn, and it’s all geared toward freelancers. If you’re near Sydney, you can join us in person and for writers in the rest of the world, there’s a virtual option. All the ticket options are available here. If you come, please say hi!

Earlier this summer our dachshund rescue was low on money and I was low on work. So on the spur of the moment, I launched coaching sessions for writers in exchange for a donation to my rescue. I was shocked that all of my spots filled up in a few hours. I thought I would be lucky if 10 people signed up. I launched the program to help the dogs and help other writers. And if you missed the registration, I’ll be doing it again in the fall – although probably on a bit of a smaller scale. 

But in the end, I got so much out of the calls. And I learned so much about the current climate and struggle. 

Here is what I learned from talking to 60 writers this summer:

Almost every writer had a slow summer. It wasn’t you. It was the market. I only talked to one person who wasn’t slow or at least slower than usual. So if your work has been slow in recent months, it’s not because you suck or you need a new career. The economy and business is cyclical, which means freelancing as a result comes (and goes) in waves. For years we’ve been at the top and now we are at the bottom for the past few months. I also think we are back to the trend of slower summers that we had pre-Covid with things picking up in late August and early September. I’m already seeing signs of things picking up and I keep hearing the same from other writers so hopefully things are going to be looking up. 

You are not alone if you suffer from imposter syndrome. Most of the calls turned into a therapy or at least cheerleading session. I had no idea how many writers felt that they weren’t good enough and took every rejection personally. I thought it was just me. You are not alone if you suffer from imposter syndrome. Since it’s such a common challenge, I’m going to devote a blog post to it in the near future. In the meantime, check out this fabulous episode of the Deliberate Freelancer on the topic

Look at past (and current) full time jobs for niches. I really think that it’s hard to be successful if you don’t have the right niches for you. And yes, you can be a generalist as long as you present yourself as an expert in the niche of each company you are approaching. It’s hard to find the right niche; it needs to be one that’s high paying and one that you enjoy. 

Niches were a hot topic during the calls. And many times, a person mentioned a past job in passing, such as a realtor or insurance agent, and when I suggested that as a niche, they were shocked. Even if you don’t have many or even any clips in a niche that you worked full time in, that’s likely very OK. You can use your other clips to show writing combined with your full time work history. Take a minute and look at your resume and LinkedIn. Ask yourself if there are any past jobs – even something as simple as working retail after college – that you could use to break into a new niche. And then use the audience first method to find new clients to contact.

Most writers are underusing their personal networks. I heard time and time again how people didn’t want to bother people in their network. Or that they hadn’t kept in touch well. I highly recommend staying in touch and reaching out to professional connections from college, past full-time jobs, even neighbors who work at companies in your niches. The people you contact don’t need to be in the position of hiring—they just need to work at the company and be willing to give you an introduction. If you are a journalist who worked in a newsroom, odds are very high that you have co-workers now at many different companies, publications and organizations, so don’t overlook this resource. 

Writers overthink EVERYTHING.  I do the same thing. So it was super interesting to me to watch so many writers having the same conversation out loud that I often have in my head. People would spend 10 minutes explaining why something wouldn’t work or all the reasons they didn’t want to do something because they were worried something could happen. Or spending weeks trying to decide the best niche or way to market.  And then they had basically talked themselves out of doing anything and were now doing nothing.  I’ve got a post addressing how to overcome this in the very near future. 

The most successful (and happy) writers have a strong network of other writers. Writing is a solitary venture. And many of us are introverts. But the writers I talked to who were thriving the most were those who had other writers for support, lead sharing and bouncing ideas. Sure, it’s great to post in my Freelance Content Marketing Writer group on Facebook and have that camaraderie. But I feel strongly that we need more than that to really thrive. We need someone we can call when we have a pricing question or if we need validation to drop a client.  Other writers are our colleagues, not our competition. One of my biggest suggestions throughout the calls was for writers to create their own mastermind/accountability group with writers in their niche or income stage. 

Do what works for you. One writer opened the call by telling me that she knew I was going to tell her that she needed to send out LOIs. She said she hated doing them and had much more success with networking. She was a bit surprised when I told her that she absolutely should not send out LOIs. If something doesn’t work for you, then don’t do it. Each of us has different personalities and different target clients, so what works for one writer isn’t the magic bullet for others. So if conventional advice doesn’t work for you on something, then ignore it and do what is working for you. 

Freelance writers are amazing and interesting people. When you say it out loud, 60 coaching calls in 4 weeks sounds like a lot. And it was. But I really enjoyed getting to meet so many wonderful people and hopefully new friends. I really think that we are a special type of person and I really loved getting to know so many people. And we raised a significant amount of donations to help dogs in need, so everyone wins.

What are your thoughts? If you did a coaching call with me, what did you learn? 

 

16 Comments

  1. Erica Patino on August 15, 2023 at 12:24 pm

    Hi Jennifer, I was, I believe you said, the third person you spoke with. I am a more established freelancer already (in a niche for 15 years), and I was impressed by how quickly you zeroed in on new ways for me to market myself. I learned to think differently about my skill sets and have more confidence. All the points you mentioned above to apply to me! Thanks for the wonderful coaching call.



    • Jennifer Goforth Gregory on August 15, 2023 at 12:38 pm

      Thank you for the kind words! I am so happy that I was able to help you so much. You made my day .



  2. Melissa Gerke on August 15, 2023 at 4:52 pm

    Hi Jennifer,

    Overthinking everything and then doing nothing is a trap I’ve fallen in a few times!



    • Jennifer Goforth Gregory on August 15, 2023 at 9:50 pm

      You are in VERY good company. I never realized how many writers do this. I honestly thought it was just me.



  3. Christine gomolka on August 15, 2023 at 6:21 pm

    Damn this was good! Thank you!



    • Jennifer Goforth Gregory on August 15, 2023 at 9:50 pm

      What a great compliment. Thank you!



  4. Alice Dubin on August 15, 2023 at 8:27 pm

    Excellent post and insight. Thank you as always!



    • Jennifer Goforth Gregory on August 15, 2023 at 9:50 pm

      Thank you for the kind words!



  5. Margie Zable Fisher on August 16, 2023 at 6:24 am

    What a terrific post! Especially loved Writers Overthink Everything. So true! And we can’t say it enough – thanks for all you do, Jennifer!



    • Jennifer Goforth Gregory on August 16, 2023 at 9:04 am

      The overthinking thing was a big revelation for me from these calls. And then I started recognizing it in myself. The biggest thing was that the writers were exhusted from it and felt like they had done so much and weren’t getting any work, but in reality they had done no actual outreach.



  6. Julie Sturgeon on August 16, 2023 at 12:03 pm

    You know I’m a big advocate for community — and that community isn’t social media! It’s more private and therefore more intimate than LinkedIn.

    You need both!



    • Jennifer Goforth Gregory on August 17, 2023 at 8:19 am

      I agree with you a billion percent. My strongest writer relationships are those I met in person.



  7. Jennifer Fink on August 16, 2023 at 3:32 pm

    Point #1 is reassuring! I’d gotten the same impression, but it’s nice to hear you *also arrived at that same conclusion, after talking w many more writers than I did. My June was slow — which was fine, b/c spring had been really busy & I needed a break. I let June be slow. By July, I was like, I should do something about this…I worked on some marketing and yes, August is already much better. (Honestly, I’m not sure how much/if any of that was due to marketing and how much would have happened anyway).
    Looking forward to hearing what you have to say re over-thinking ’cause yeah, I do it too.



    • Jennifer Goforth Gregory on August 17, 2023 at 8:24 am

      I also felt so reassured talking to other writers that they were slow as well. It made me feel SO much better. I’m seeing the same thing with August. I think that the market naturally picked up but those of us that marketed in July are likely seeing a bigger pickup because we put out the feelers and got positioned. And yeah, I do it too with overthinking.



  8. […] feeling less than other writers or decides that they need a new career because they suck. After talking to 60 writers this summer, I realized how prevalent it really is – it came up in some form during pretty much all my calls. […]



  9. Alex on August 23, 2023 at 12:06 pm

    Hi Jennifer — are you still taking on new coaching clients, just for a session or two?