Working online as a creative writer from Jamaica

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How It All Started

I got into freelancing by chance. It all started in 2011. My older son and daughter-in-law had an Upwork (oDesk at the time) account and did content writing jobs. When jobs got too much for them or they were particularly rushed, they would enlist my help (without pay) and I was more than happy to help them out. It was mostly product descriptions at first and very eye-opening for me.

I recall one particular job which called for dozens of “unique, creative, and enticing” descriptions for near-identical food canisters that only differed in terms of colour or pattern. There were also article spinning jobs for clients who, for instance, had multiple websites offering the same exact service but needed for each site’s content to be unique. It all seemed ridiculously inane at times but I think my love of language and the written word allowed me to rise to the challenge.

Over time, they got other jobs, involving research, article writing, and eBook writing on topics I could really sink my teeth into. I think that was when I got hooked on freelance writing. They started finding jobs just for me that I could do in the evenings after coming home from work as a fulltime high school Math and Science teacher. Better still, they started paying me whatever I earned through them! I spent a couple of years writing part-time with them and looking back now, I am really quite grateful I got into freelancing that way.

My Situation Changed – Drastically

I had to give up my full-time teaching job to stay home with our toddler. Leaving teaching was not an option I had entertained before that. I had spent 18 years in the classroom teaching from the Early Childhood to the Secondary level and, believe me, I was really looking forward to at least 15 more years doing something I thoroughly enjoyed and was good at.
I was more than prepared to continue working but we realized from early on that this child was simply different from our two older children. I was constantly exhausted trying to keep up with our young son. I used up all my sick leave AND special leave, and was at the point where my doctor wanted me to seriously consider sleeping pills.

My husband and I talked it over and decided that although essentially cutting our income in half would make things really rough, my health was more important. Plus, our little one, who would later be diagnosed with severe autism, would benefit greatly from one of us staying home. This prompted my leap into full-time freelancing.

I Branched Out On My Own

For a few more months, I continued writing as before, taking whatever jobs my son and daughter-in-law got for me. Then, I decided to give full-time freelance writing on my own profile a go. I had the experience and my son’s profile had always received good feedback on jobs I did for them. I figured I could set up my own profile on Upwork and build it from scratch and that is exactly what I did.
In the beginning, I just needed to get positive feedback to build my profile. So, I wasn’t too choosy about what jobs I applied for and I worked at ridiculously cheap rates. It is what many, if not most, new freelancers have to do – comes with the territory, I guess, or perhaps it’s some kind of rite of passage. Looking back now, I have no regrets that I made the sacrifice and stuck with it until I was able to improve my rating and raise my rates.

What I Offer

The vast majority of my work is article writing. I do articles of various lengths and on a wide variety of topics. I specifically go for science, education, and health (in particular mental health and overall wellness topics). I also enjoy writing lifestyle type articles and anything that fits into my other interests, history and geography. I definitely do not apply for writing on topics where I don’t feel I could possibly do them justice, no matter how much research I do!
I also write eBooks on various topics, plus do editing and proofreading. My Math and Science teaching background means I can take on a tutoring job every once in a while if the conditions of the job (time and medium) are favourable for me.
I live in Jamaica so my native language is English. The good thing for me as a writer is that Jamaican English is very much like UK English. Due to the country’s close proximity and close ties to the US, however, US English is no problem for me either. I can apply for jobs which simply say English or which specify either US or UK English.

My work is 100% remote. I have never sought out local jobs. I guess because I have a steady stream of work via the online platform that I use. Plus, I am not sure how available such jobs would be. Also, modern technology makes applying, interviewing, and getting paid for remote jobs easy and hassle-free. Conferencing and shared work platforms such as Asana and Slack work very well at creating a feeling of real teamwork regardless of the distance between team members. I have stuck with Upwork since the platform is complete in the services it provides and payments are secured depending on the approach you take when accepting jobs. The fees are initially somewhat steep at 20%. Fees can be lowered to 10%, then 5% over time but you have to have well-paying clients or long-term jobs to achieve those rates. I don’t mind the 20% fee (much!) since there is never a shortage of jobs on Upwork and I know my payments are secured by the platform.

Making Freelancing Work for My Family

The most challenging part of freelancing for me is that work comes in waves. Since I ask for higher rates than the average writer on the platform, I have to search for clients who are willing to pay for the quality I provide. I know that at cheaper rates, there would be a tonne of work out there to apply for but I prefer to work this way – where I stick to my high writing standards and get paid a decent enough rate for it.
My income as a freelance writer has never matched what I got as monthly take-home pay as a teacher. There have been a few months when it came close because I was fortunate enough to land a really good job or two. For the most part, however, I earn much less. My husband and I have to do some pretty fancy budgeting footwork to make ends meet each month.
As far as health insurance goes - it’s tough. As public school teachers, my husband and I had identical policies and enjoyed doubling up on benefits. Now that we are down to just his health insurance, we have not been able to go an entire year without draining the optical, dental, and prescription balance on his card long before the year is up.

Apart from losing health insurance, I no longer make pension contributions and we have to be planning for what that means for our retirement. There is also a national housing benefit that we tapped for a very low-interest loan when building our home years ago. I no longer make contributions to that scheme and so I am virtually ineligible to apply for future benefits there. ALSO, all loan repayments now come out of my husband’s salary. That includes mortgage, education loans, and car loans (we gave up one of our two cars, by the way, when I quit my teaching job).

Freelancing is all about flexibility and for me that is the high point of being a freelance writer. I can work and still devote time to my special needs child that I would not be able to do otherwise. I won’t lie, the salary and benefits would be great to have if I had continued teaching. A big chunk of that money, however, would have gone to paying for sitters and transportation to and from school and therapy sessions for him – things I am able to take care of because I freelance from home. Any kind of financial cushion for freelancers would be greatly appreciated. Something like a universal basic income, for instance, would, I think, help any freelancer. Our work ebbs and flows and as a result, so does our income. We do not have job security and must often go through periods of time when there is no work and thus no income, a situation that continually drains away any emergency funds some of us are able to tuck away when work is available. Things like paying for health insurance or investing for retirement seem like mere wishful thinking.

All things considered, I can honestly say I enjoy freelancing and freelance writing. After almost a decade freelancing, I have built up a profile I am proud of. I have clients who have been with me for years, coming back every so often to seek out my services. I have learnt new skills and become a real pro at time management (a necessity for any freelancer).
Author: Jacqueline Samaroo