My story so far, and my plan for life-changing growth

Jill Curry
March 28, 2021

If someone had asked me six months ago what I thought the life of a freelancer would look like, I don’t know that I would have a clear answer. But only two months into freelancing, I know freelance work is going to change my life.

Triggered by under-employment

My professional life has essentially been sales, customer service, management, and HR/onboarding in small businesses. I have found a huge amount of success in my career and find that I typically leave jobs because I “top out”. I reach the point where my employers are not willing to pay me more money, and they cannot promote me anymore without selling me a piece of the company (also something they are not willing to do). After reaching this impasse, I resign and move on to start the cycle over again.

In 2020, in the wake of the global health crisis, I spent a few months laid off from my position as a general manager of a boutique furniture store, and then upon the community reopening and my return to work, I chose to resign in part because of the owner’s poor handling of the COVID-19 situation, and in part because I had “topped out” again.

I moved into an administrative position that paid a little less money but that looks like a great fit and that has a lot of room to grow. The caveat was that it was seasonal and based on year-long contracts. When winter came, I was going to be laid off until spring.  Having already spent more time than I wanted to be laid off from work, I negotiated with my employers to work part-time through the winter. This was a great improvement but was not what I wanted.

I wanted consistent work paid at a fair wage for my education and experience, and I was tired of the three/four-year cycle of “topping out”.

Finding freelance

I knew what freelancing was, sort of. I knew that it was an independent contractor selling their services on a per-project basis to a client. However, I didn’t know the extent that it could go. I had always imagined freelancers exclusively in the photography or journalist space – basically, my idea of a freelancer was Peter Parker selling his pictures of Spider-Man to the Daily Bugle, but not actually having a job at the Daily Bugle.

Two weeks into my part-time winter schedule, my partner started showing me TikToks from freelancers talking about their business, and their success. He said, “you can do this.” And I agreed. As a Christmas gift, he purchased online courses on freelancing, and I absorbed those courses, and every video, blog, Tik Tok, and YouTube video I could find on how to build a successful freelancing venture.

Building the business

While I understood that mistakes will happen and that changes could be made along the way, I wanted desperately to get it right the first time. I spent about 5 weeks planning out the strategy for launching my freelancing venture.

Step 1 – What IS my business?

If I was going to be a freelancer, I had to know what I was going to sell. I wasn’t a photographer or a moon-lighting super-hero, so the Peter Parker angle was out. So what was I? A manager. A small business expert. An HR specialist. This was a great starting-off point.

I decided that I was going to offer services to write resumes and cover letters, do interview coaching on Zoom for people looking for a job, and do hiring practice consultations for business owners that are frustrated with high-turnover and who need help figuring that aspect of their business out.

But there was something else, I also love anything creative. Through my research about freelancing businesses, I learned that blog writing was an enormously in-demand service. I thought, “I can do that!” I was an English and History double major in University, so I am confident I can write. So I decided I was going to offer blog writing also.

Step 2 – Get it ready and LAUNCH

There is nothing that can make you feel “ready” to launch a new venture. All you can do is get it ready and have everything in order, take a deep breath, and launch. I decided that while I was new I wanted to use social media, word of mouth, and my website to drive traffic to the freelancing platform Fiverr, and that until I was ready to make freelancing my full-time job, I wanted to keep all sales on the platform.

Deciding to sell on Fiverr exclusively was a good choice for me because I wanted the protection of a customer service department and access to their customer acquisition model.

So, I got my partner (who is an amateur photographer) to take some portrait photos of me to be used on the platform and for social media posts.

I bought a domain name, made a logo, and built my website.

I opened Gmail, Facebook, Instagram, Linked-In, and Tik Tok accounts for my business and scheduled a few social media posts.

Lastly, I built my Fiverr profile. I decided to start with three gigs: resume and cover letter writing, blog writing, and small business hiring practice consultations. I determined my pricing and decided to list “new seller promo” packages starting at just $5. I wrote my descriptions and took a deep breath.

Everything went LIVE on January 28, 2021.

And then… Nothing happened.

Nothing happened. Nothing. I didn’t even get spam messages.

Even reaching out to buyers didn’t work out. I was not getting sales. As a professional salesperson, this was confusing to me.

So I did two things:


Three weeks in, and the day after my Instagram story feature and raising my prices (coincidentally, this happened on the same day), I got four orders within about 14 hours. One was from my friend’s Instagram shout-out, one was from a Fiverr buyer request that I had bid on, and two were completely organic.

Snowball effect

Those four initial orders all resulted in five-star reviews, three of them turned into repeat clients, and it started to snowball FAST.

Within two weeks, I had consistent orders and frequent messages from prospective buyers that I was able to close deals with. By day fifteen, I had to raise my prices so I could keep up. I doubled them.

After doubling my prices, my impressions and orders increased, especially on my blog writing gig, and I worked to the point of exhaustion to get everything completed, on time, and with the highest quality.

Within another week, I had to raise my prices again, and four days after that, raised them again. Six weeks ago a 1500 word blog would have cost you $25, and will now cost $95 and they are still selling at that price. I am now at the point where I am turning down new clients because the repeat clients I have are keeping me busy, and do not seem deterred by my new prices.

By the way, Fiverr works on a “level system”, which divides sellers based on experience and sales satisfaction. I am still an unlevelled seller, and will not be making level 1 until April 14. Is this normal growth for a new seller? I don’t know. Does it work for me? YES.

How I am going to change my life with freelancing

My long-term goals with freelancing are to match my full-time salary and move to freelance full-time. Once I make that transition, I would like to make over $100,000 a year from it. To make $100,000, I must earn at least $400 per day for each of the 250 business days in a year. Is this possible for me through freelancing? YES!

Selling $400 a day on Fiverr, and still having weekends and holidays off would change my life in the sense that I would be earning enough to live very comfortably. But more importantly, I would also prove to myself that I can work for myself.

I will own a registered and incorporated business, and I will be collecting all of the profits myself. I will no longer be at the mercy of another business owner who is not willing to pay me more. I will determine how much money I get paid. I will determine when I am allowed, or not allowed to take a vacation or a sick day. I will determine the office dress code. I will determine whether or not to take on that difficult client that no one else will work with.

Freelancing will be my route to independence. And that will change my life.


Jill Curry is a 32-year-old freelancer and small business expert who is actively working toward working for herself. Writing has proven to be a real love of hers and she hopes to continue pursuing this passion into retirement. She lives in Northwest Ontario, Canada and spends the small amount of free time she has enjoying the outdoors, hiking, and fishing. Visit to learn more about this rising star.