3 Challenges I Face as Full-Time Freelance Writer (Or, why I wish there were freelance writing storks)

When I was a kid, I thought salespeople were sleazy. All of ’em. I remember getting into an intense argument with one of my childhood friends when she said my Dad worked in sales. How dare she say that?! (FYI: He does. He’s a business owner.)

That was clearly a juvenile understanding of sales (i.e. all salespeople go door-to-door and try to rip people off). As a 25-year-old sole proprietor, I realize that’s a SUPER inaccurate perception. Nonetheless, it still took me a while to recognize that every business owner, freelancer, independent contractor–you name it–is effectively a salesperson. And more importantly, salespeople do not need to be sleazy.

You can be ethical and successful.

Which brings me to my list of 3 challenges. Number one–you guessed it–selling.

Challenge One: There are no storks in the freelance world. Nope. You gotta go get your own work. And while this can be challenging, it’s possible. To give you a feel for where my work comes from, I’ll break it down for you. (Keep in mind, I am not an employee of any company. I am a sole proprietor. This means that even though I work with other companies, I work for myself.) Here’s the breakdown:

  • I write 10-15 pieces (i.e. articles and emails) each month for a small digital marketing agency.
  • I ghostwrite 2-4 pieces each month for CEOs, founders, and industry leaders.
  • I team up with other freelance writers and large agencies to write 2-4 articles each month.
  • I write an average of 2 articles each month as a contributing writer at internships.com (Here’s an example.)
  • If I have room in my schedule, I add other projects: resumés, cover letters, LinkedIn profiles, formal letters, or web copy. It’s a wide variety–and I love it.

Now you’re probably thinking:

Okay, that’s good and all, but how do I find freelance writing jobs if I’m just getting started as a freelance writer?

Here are twenty ways to find freelance writing jobs. You can send cold pitches, inform your LinkedIn connections, or ask family and friends. In this post, I share how I landed my first freelance writing job. (Spoiler: it was with a complete stranger through Upwork.)

Challenge Two: Employee benefits. What employee benefits? Here’s the deal. There are benefits to working full-time as a freelance writer (Read: 5 Reasons I Love Working in the Gig Economy). But when I quit my job in October 2016, I gave up traditional benefits. Sayonara, guaranteed salary! No more employer healthcare or matching 401K contributions. Do I wish I had matching 401K contributions? You bet! But…

At this stage in my life, the pros of being a full-time freelance writer outweigh the cons. I still have healthcare, money for student loans, and money for retirement. (Plus, I have a solid emergency fund in place.) And best of all, I have freedom. This year my traveling time will equate to more than three months.

Challenge Three: Friends? Co-workers? Where are you? True story: I can go an entire work day without talking to another human being. Some days this is fine. Everyday? Not okay. (Unfortunately, all my friends still work 9-5 jobs. Boo. Come be a freelancer with me.) Jokes aside, a lot of freelancers agree: working remotely can be lonely. Here’s how I deal:

  • I joined the YMCA (for the group classes). Each week, I map out which sessions to attend. This is guaranteed social interaction (and a way to center myself and refuel). These sessions also provide much-needed structure to my day. For instance, if it’s a 12:30 PM class, I write an article in the morning–with a forced end-time of 12:00 PM. Then I take a forced well-deserved break before I resume working in the afternoon.
  • I tried out a co-working space. I found co-working helpful but I actually do better with more flexibility. I enjoy working in a variety of spaces (Monday: library, Tuesday: coffee shop, Wednesday: college campus). My frequent travels also make it hard to justify a monthly membership. So, I cancelled my membership. That being said, I’m a huge proponent of co-working spaces and highly recommend checking out your local space.
  • I work in the presence of other people. Though the co-working space doesn’t logistically make sense for me, I know I benefit from working in the presence of other people. I regularly spend half days at local coffee shops. Arriving around 9 AM, grabbing an iced tea for $2, and hanging out until early afternoon. I am consistently more productive when I’m surrounded by other people.

So yes, there are challenges to being a full-time freelance writer. (And not to be the bearer of bad news, but the freelance lifestyle does not work for everyone.) Some people are too afraid–of selling, failing, or networking–to ever get started. Other people cannot financially support themselves and their families without traditional employer-provided benefits. (I wish this wasn’t reality!) And other people thrive in an office environment with co-workers. None of these things are good or bad, better or worse, they just are.

As a part-time freelance writer, you can avoid challenges #2 and #3; focus on tackling #1. If you want to be a full-time freelance writer, weigh the pros and cons of your unique situation. You will undoubtedly be impacted by all three challenges, but that does not mean that being a freelance writer is a bad idea. (It may be the best idea.)

Freelance writing can be challenging but it’s so worth it.



Hey, I’m Laura. In October 2016, I quit my job (on purpose) and became a freelance writer (on accident).  Now I share my experience as a freelance writer for 20-somethings. Because contrary to popular myth, you don’t have to wait until you’re 50 to become a successful freelance writer. I’m happy you’re here.

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2 Comments

  1. This is so great. I recently started a blog and it feels like I’m failing but I am loving every second of it. I graduated with a Math major so needless to say words don’t come easy to me. But I am doing it. Also, the advice on working at coffee shops/libraries/etc is something I am going to try this week. It’s tough not seeing anybody for days. So thanks!

    1. Awesome, Brianda! Thanks for stopping by and congratulations on starting a blog–love the name btw. I definitely think it’s normal to feel like you’re failing. Starting a blog and growing an audience is a long process but as you already know, it’s worth it when you love it!

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