Expert Roundup: The Scariest Obstacles Freelancers Face

Expert Roundup

You’re in for a treat, fellow writers, because over the past two weeks I’ve had the privilege of chatting with ten talented, kick-butt freelancers who have agreed to give you input on some of the most daunting obstacles they faced starting out in their careers. The fact that all ten are women is a coincidence I didn’t really notice until I started receiving responses back, but I love the girl-power going on nonetheless. These are women who have been at this longer than I have and who are making their full-time incomes on a steady basis. They work in a wide variety of freelance writing fields, from blogging to business-to-business copy writing, and they’ve provided solid advice on tackling problems you are likely to face when you start your writing career.

The Question:

Besides taking the initial leap of deciding to become a freelance writer, what was the scariest/most nerve-wracking obstacle you faced starting out, and how did you overcome it?

The Answers:

1. Gina Horkey:

In addition to being a traditional freelance writer, Gina earns her five-figure monthly income by working as a virtual assistant, creating freelancing courses, blogging on Horkey Handbook, and coaching other freelancers.
Find Gina at: Horkey Handbook

“Whew, I think it was after I decided to leave work behind and had to tell my employer about my plans. It wasn’t a two-week notice type of thing and I owned my own client base, so while I was hopeful that they would offer to purchase it, I was scared outta my mind!

I was the breadwinner (my husband a SAHD to our two toddlers) and it was all on my shoulders—or at least that’s how it felt. I handled it by preparing in advance as much as possible, scheduling a meeting and being honest about my intentions. Thankfully they were incredibly supportive and due to our strong relationship, it worked out as well as I could have imagined or asked for!

The other thing that I did to prepare was build up my business as much as possible while working full-time. That way, if their response wasn’t as favorable, I was as prepared as I could be to make the leap and start freelancing full-time.”


2. Jorden Roper:

In just four months, Jorden made a four-figure income writing blog posts on marketing and B2B topics for companies. She’s also the no-holds-barred writer of Writing Revolt, a blog tailored to helping other freelance writers kick-start their careers.
Find Jorden at: Writing Revolt / Cutthroat Copy

“The thing that stressed me out the most as a newbie freelance writer was phone calls with intimidating CEOs and marketing executives! When you’re starting out, it’s tough to know how to sell your services over the phone.

Even though it was nerve-wracking, I’m so glad I didn’t chicken out of those client calls—lots of them resulted in long-term business relationships.

Here are a few things I did to get over my fear of client calls:

  • Prepared a client cheat sheet in Evernote before the call – Each cheat sheet had several key points about the client’s business and how I could help them. Sometimes, I’d also include answers to the questions I thought they might ask. (If you do this, it’s important to avoid reading your notes word-for-word. Think of it more like a resource you can reference quickly if you get stuck!)
  • Took phone calls first thing in the morning – Getting the calls done right away helped me cut down on time I spent nervously anticipating each call, so I felt a lot less anxious on the phone.
  • Looked at testimonials from happy clients before each call – Checking out comments from previous clients who enjoyed working with me gave me the boost of confidence I needed to power through each call.

If I felt really nervous about the call, I’d also have a beer or two to help myself relax! Why not, right?”


3. Alicia Rades

Alicia is a professional blogger who specializes in writing for small businesses. She is also an award-winning YA novelist.
Find Alicia at: Her Freelancing Website / Her Author Website

“The scariest thing for me was learning to get outside of my comfort zone, whether that was writing about new topics or taking on new clients. I started by writing for some content mills, and even though I knew I’d make more money taking on private clients, I didn’t want to do it. At the same time, I knew that if I wanted to do this as a career, I had to take action and move up. With the encouragement and help from other writers, I took on my own private clients, and I’m so glad I did because I wouldn’t have made a career from writing if I’d stuck inside my comfort zone.”


4. Sharon Hurley Hall

For over twenty-five years, Sharon has shirked the idea of a niche, and it hasn’t held her back one bit. She works as a blogger, feature writer, and e-book ghostwriter for businesses, entrepreneurs, and bloggers. If you name it, she probably does it, and does it well.
Find Sharon at:

“Besides taking the initial leap of deciding to become a freelance writer, what was the scariest/most nerve-wracking obstacle you faced starting out, and how did you overcome it?

One of the hardest things I faced as a new freelancer was knowing what to charge and having the confidence to charge what my writing was worth. I know that many writers struggle with this. I had this idea that there was some mysterious ‘going rate’ that all the more experienced freelancers knew but I didn’t. I also worried about how potential clients would perceive me if my rates didn’t match their expectations. And I made some of the classic new freelancer mistakes like underestimating my time and undercharging for work that required a lot of effort.

I overcame this in three ways:

  1. I got informed, reading everything I could about recommended rates for different types of writing (Writer’s Market and the Editorial Freelancer’s Association were helpful) and about how other writers handled it.
  2. I used a time tracker, Rescue Time, so I knew how much time I spent on different writing jobs and could estimate my time commitment more accurately.
  3. I used both sets of information to create my own internal rate sheet and used that when providing estimates.

Two mind shifts helped with this process:

  1. Knowing that what I did had value for my clients.
  2. Realizing that it was up to me to treat my writing as a valuable business service and that I was in charge of my ideal income, NOT my clients.

I’ve never looked back. These days, I publish my rates on my website and the conversations with clients are very different from in the early days.”


5. Lauren Tharp

Lauren creates online content for small businesses and entrepreneurs and provides one-on-one mentoring for freelance writers and bloggers.
Find Lauren at: Little Zotz

“The scariest obstacle I had to face, besides my own fears, were the prominent naysayers in my life. ‘Why don’t you get a REAL job?’ was their constant refrain. And their opinions really dug deep because I desperately needed money when I was first starting out and getting a ‘real’ job with a steady paycheck was very tempting. However, I kept at it and, within three months of making freelance writing my sole source of income, I was earning a decent living—and there is nothing like earning money from what you love to shut up the naysayers in your life once and for all!”


6. Sarah Beauchemin

Sarah focuses her freelance writing talents on cause-driven organizations and subjects such as the humanities, lifestyle, and culture. In addition to her blogging and writing, she provides content strategy services.
Find Sarah at:

“The scariest obstacle I faced starting out was myself. I constantly questioned my ability to write, to attract and retain clients, and to ‘keep up’ with others in the industry. I think every creative person struggles to some extent with this kind of anxiety, or ‘imposter syndrome,’ but it’s even worse when you’re just starting out as a freelancer. The only way I successfully managed these anxieties was by taking action. Each day, I made a list of 3-4 things that I believed would help build my business—writing a killer blog post, reading other writers’ blogs and connecting with them on social media, pitching guest posts, applying for a gig, etc. Even if none of these things yielded immediate results, I felt more confident that I was headed in the right direction. It’s so true that confidence comes from action.”


7. Elna Cain

Within six months of starting her freelance writing business, Elna was making a full-time income working part-time as a stay-at-home mom to twins. She makes her living through B2B writing, blogging, and coaching.
Find Elna at:

“I’ve been a freelance writer for almost two years now and there have been many nerve-wracking instances.

One in particular involved my first ever phone interview—which turned out to be my first writing gig. See, before I became a freelance writer I was a stay-at-home mom. I have twins. And before this? A teacher.

I never really had experience doing a phone or Skype interview. I knew I should prepare for the interview, so I wrote a few questions to ask my prospective client.

But, when the time came, I ended up saying a lot of, ‘ummms’ and ‘uh-huhs.’ I forgot to ask my questions and I had a difficult time explaining how I could help their content marketing strategy.

When it was all said and done, I was convinced I bombed the interview and they would never in a million years hire me. But, a day later, I got an email from them saying that they would like to hire me for my writing!

It goes to show that even though you might be nervous, fearful, anxious or worried, if you put yourself out there and take action, good things will happen! So, go out there and do it!”


8. Francesca Nicasio

Francesca runs the advice-driven site, Be A Freelance Writer, in addition to creating web content for clients and providing mentoring services to freelancers (not to mention the great stuff in her free e-books).
Find Francesca at: Be a Freelance Writer

“The scariest obstacle for me was getting the nerve to approach potential clients and sell myself. I was quite shy (still am), and I wasn’t a fan of salesy tactics. I felt like I would be bothering prospects if I reached out and told them about my business.

I overcame this obstacle by changing my mindset. I realized that I was running a freelance writing business and I was providing a much-needed service to other *businesses* — NOT consumers.

This is an important distinction because selling to businesses is very different from selling to consumers.

Consumers slam doors and hang up on salespeople because they really do feel like they’re being bothered. There they are, busy with work or watching TV and some guy calls or shows up trying to shove a product into their face.

But entrepreneurs do not think or behave the same way. When you reach out to them, they won’t see you as a pushy salesperson (unless you really are being pushy or obnoxious). Rather, they’ll likely see you as another business person just like them, trying to make a living… just like them. You’re a legit business offering something of value to another business.

Once I internalized this, everything changed. This realization helped me muster up the guts to approach companies with my services. I started cold-emailing businesses, I spoke to entrepreneurs in my network, and I told everyone I knew to spread the word.

All these actions helped me land several clients, and the rest is history.”


9. Corinne Kerston

Corinne is a blogging wiz, and she helps others generate income through their blogs with her in-depth courses and content writing services.
Find Corinne at:

“For me, the scariest part was putting myself out there. It took some self-convincing to even put my photo on my website and really brand myself! But I knew I had to do it. If you want clients to hand over their content needs and allow you into their business and their lives, they have to trust you. And part of that trust is allowing them to learn more about you as a person. It might sound like it’s not important, but clients love to put a face to your services. And I still struggle with cold pitching, even though I know it’s highly effective. I do much better with inbound marketing and letting clients find me.

How did I overcome it? Not sure I ever completely did. It’s the introvert in me. But I will say that it gets easier over time. The more I put myself out there and succeed, the easier it is to convince myself.”


10. Noemi Twigg

Noemi is the community manager of Freelance Writing Gigs (a freelancer job board that I am on literally every weekday) and the editor in chief of Splashpress Media.
Find Noemi at: Twitter / Freelance Writing Gigs / Splashpress Media

“My biggest fear was uncertainty regarding income and the fulfillment of my dream. We know that going freelance full-time does not normally equate to regular income, and that was a big worry. I’ve been very fortunate to have steady work and awesome people to work with, so my fear turned out to be unfounded. One word to overcome this ‘problem’: hustle and just do a good job consistently.

Regarding the uncertainty of fulfilling my dream, it’s a bit more complicated. There’s this saying that sometimes, your dreams aren’t all what they seem to be, that when you live them, you turn out to be disappointed because they fall short of your expectations. In my case, I didn’t have to do anything actively to overcome this fear. My dream of freelancing full-time turned out to be pretty much what I thought it would be.”


Thanks for reading! I hope you’ve been adequately inspired (How could you not be?). Now go check out these kick-ass ladies and their work.

22 thoughts on “Expert Roundup: The Scariest Obstacles Freelancers Face

    • IJustWanttoWrite says:

      I am so glad this post helped you! Nothing like a bunch of no-nonsense career women to get you in gear.

      Writer’s block sucks. One of the things that has worked for me is to view writing my blog posts as part of my business, something I have to do not only because it’s part of my job but because it provides something informative and enjoyable for others (sort of along the lines of what Francesca was talking about in her answer). That gets me in gear.

      However, writer’s block in fiction is different. In that case, I just have to force myself to sit there and write something. The first few paragraphs I squeeze out usually aren’t very good, but that’s what editing is for. I find that once I make myself write, I settle into my groove pretty quick.

      Thanks for commenting. Go kick that writer’s block’s butt!

  1. Elna Cain says:

    Thanks so much for including me in this roundup of some awesome freelance writers. There definitely is a lot to learn as a newbie writer!

    • IJustWanttoWrite says:

      Of course, Elna! Thanks so much for contributing, being the awesome freelance writer that you are.

      And yes, there definitely is. As soon as I think I’ve got all my stuff figured out, something else pops up. But hey, it beats the crap out of my old waitressing job.

  2. corinneck says:

    Hi Hannah, Thanks so much for including me in your roundup. Starting out can be scary for sure. It’s great to know everyone has some fears, no matter who they are!

Leave a Reply