How I Went From IT Salesman to Copywriter in 6 Months

It may have taken half a year, but it was worth every fiver.

Will Anthony
ILLUMINATION
5 min readJan 9, 2022

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Image by Austin Chan on Unsplash

If you’re a freelance writer or something of the sort, you’re likely aware of Fiverr as a springboard for new wordsmiths.

It’s a breeding ground for novice diction, lacking structure, and the rates to match. But one would argue that’s the beauty of it.

After all, it’s what polished the sharp edges of my writing expertise and gave me the confidence to eventually pursue private clients.

From there, landing a full-time writing gig just took a bit of hope and rigorous outreach. Sorry, but switching your career isn’t an endeavor void of effort.

Are you supporting your writing with another job, or striving to turn words into your career?

Just a year ago, I was working a cold calling sales job. Writing until the early A.M. and running on fumes after cold calling 100 plus strangers for eight hours.

Here’s my trajectory over the past several months, from IT support salesman to copywriter and magazine writer.

Square One

While selling the most boring product you could think of, IT support, I felt a bit empty. Hollow and unfulfilled.

I wasn’t doing anything I was passionate about, which gave me a feeling of unfulfillment. So I started writing about my ridiculous opinions and funny dating experiences in journal format. I never planned on publishing anything.

It was just therapeutic to confide in an opinion-less notebook.

This turned into a nightly habit. Soon, I realized words were something I was pretty passionate about. I deeply valued communication and its sheer power to inspire.

I loved telling stories, and figuring out how to craft them in the most impactful way possible.

Coming to this newfound realization that my life revolved around words, I wondered how you make money at it. How the hell do writers make money?

Novelists are one in thousands, bloggers are up and down the street, and reporters typically require a journalism degree and some experience.

I felt hopeless and aimless, until I heard of this girl named Alex Fasulo.

Following the Fasulo Formula

Dubbed the “Freelance Fairy,” Alex has made a name for herself as one of Fiverr’s highest earners in recent years.

If you’re not aware, Fiverr is a freelance platform popular amongst writers to earn consistent “Gigs.”

After reading about her $300,000 plus earnings per year on the platform, I decided to start out the same way she did: listing each of my services for $5 a pop.

From 2,000-word articles to 300-word press releases, my prices didn’t waver for several weeks. My earnings were low, yes, and I was pulling multiple all-nighters a month, but my reviews were glowing and exploding.

Still, I recognized that it’d take quite awhile to build a freelance client base profitable enough to afford living in SoCal.

I soon decided that instead of chasing the solopreneur lifestyle, I’d find security in a contract-based or full-time writing job by using my Fiverr portfolio.

Going Bigger

While looking around for full-time jobs, I also sent out some applications for contract-based writing positions. Think blog writer positions, short-term journalists, and staff writers for magazines.

One day, I decided to directly email the publisher for a magazine in Colorado.

I told him that I was a new writer but had nearly 100 reviews on Fiverr, and was just looking for consistent work to build my portfolio.

To my luck, he ended up calling me 10 minutes after sending that email.

Good thing my number was in my signature.

Image from Arvada Lifestyle Magazine

Show & Tell

A few months after giving up sales, I was writing for a community magazine out of Colorado — and with my newfound sense of entitlement, started to raise my prices on Fiverr.

Sure, I was only earning $800-$1,000 a month at my peak, but it gave me a handful of items to privately show potential full-time employers. Plus all the content from my magazine work.

Image by Glenn Carstens-Peters on Unsplash

Apply, Apply, Apply

After these steps, all it took was some time on Indeed.

What I found was that your portfolio will not only speak to your skill, but provide the confidence to kill the interview as well.

When I first started writing articles on Fiverr, I was obviously not confident in my abilities. No one who is confident in their abilities sells them for $5 despite word counts above 2,000.

It’s the collection of work on Fiverr that gave me the confidence to call around, eventually earning me that magazine role, sparking a domino effect which landed me in the copywriter position that I now hold.

Portfolio First; Confidence Will Follow

It’s all in the portfolio, though more notably, it’s in the confidence that results from that collection of work.

Not to say you should underprice your services like I did, but piling up your experience in any way will eventually get you noticed by either a dream client, target audience, or desired employer.

After three months in my current copywriter position, I couldn’t be happier with my trajectory, and suggest it for any young writers looking to establish themselves as in-house or agency copywriters.

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Will Anthony
ILLUMINATION

Copywriter out of SoCal, fighting carpal one keystroke at a time. Rants, poetry, & helping new writers master their craft: https://bit.ly/Will_Anthony