My Start in Freelancing + Tips for Wannabe Freelancers

I’ve been reflecting a bit lately on my freelance writing clients, and how grateful I am for their awesomeness. I stumbled onto consistent freelance writing accidentally in June 2015, while Taylor and I were gearing up for our gap year. The fact that I’d be leaving all three of my university jobs simultaneously hit me hard, and I knew I needed something to fill the time (and to make money) while traveling.

I’d gotten some freelance experience prior to summer 2015, but the gigs were temporary and stressful. I wrote reviews for an insurance company (such dry material…bleh) and penned descriptions of subdivisions in Texas for a real estate company (MUCH more interesting!) Taylor and I were both hired for both gigs, and we split the workload to make it manageable between our classes and other jobs.

Taylor moved on from freelancing to pursue bigger things, and when my gigs dried up I focused on school. But then I became acquainted with Upwork, a website where freelancers can browse work opportunities from employers all around the world. I had a rough start; I had to apply to quite a few gigs before anything bit. But now, about two years later, I’ve managed to find four consistent work opportunities through this awesome website.

Workin’ away on a sunny day in Croatia

Being a freelancer isn’t quite the same as being an entrepreneur; you are still “employed” by your clients in one way or another. But freelancing does have a ton of awesome benefits, including:

*The ability to set your own hours

*The chance to control how little (or how much) work you’ll have

*The opportunity to work from anywhere in the world!

*The chance to set your own rates

People often ask me how to get into freelance writing. There are many different paths into this exciting career, but here are few things I’d recommend for newbies:

1.Build a portfolio

Don’t tell; show! Let your awesome work speak for itself. When I started searching for freelance gigs, I compiled a portfolio of my best pieces. If you don’t have past work to choose from, you can use school assignments or personal blog posts to advertise your writing style.

2.Apply, apply, apply

It takes time to build up clientele. When you start out, your goal should be to get your foot in the door. You may need to accept low-paying or short-term gigs to get some reviews. Apply to anything that is within your comfort zone, and go from there. Expect to get rejected; this is a numbers game, but over time, the fish will start to bite.

I def have days where I feel like this guy ↑


Talented writers aren’t crafted overnight. As with any skill, you have to make a concerted effort to perfect it. Master spelling, slay grammar, and crush sentence structure: you’ll need to be powerful on paper to compete with the millions of other freelancers out there.

4.Take it seriously

I’ll admit it, I’m not a natural-born entrepreneur. I perform best with a boss breathing down my neck and a deadline looming over my head. But this doesn’t mean that I’m not a self-starter! When you’ve been applying for gigs, and you start getting responses back, be prompt in answering questions, providing supplementary material, and working through the application process. Even though applying for jobs can be an emotionally draining experience, you have to go through the tough part to get to the goods


Even if your area of expertise is rabbit showjumping, being flexible with your freelance writing is key to getting multiple jobs. In the 3ish years that I’ve freelanced I’ve covered all kinds of topics, including business, real estate, marketing, travel, outdoor sports, and credit repair. I’ve learned a ton from embracing every assignment that comes my way (except the ones that involve writing other people’s school papers…that’s just plain shady, IMO). 

If you’d like to learn more about freelancing, stay tuned: I’ll be drilling down into the specifics of this trade in future posts. Next on the docket? A chat about how the term “freelancer” doesn’t have to be synonymous with the term “poor”. 

Feel free to leave your questions about freelancing in the comments. Thanks for stopping by! 

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