Jessamy McDougal – My journey to Freelancing

Freelancing always seemed like an elitist position. Something people much smarter than me did. Freelancing was for journalists, photographers, graphic designers. Not a pushing-middle-age-slightly-too-round-for-my-liking mother of five with very little to show for myself.

But I was wrong. Turns out, all I needed was a drop of talent, a smattering of skills, and a pile of guts and determination. Who knew?

People are paying me to write things. Me! It’s 10:37 at night, and I am sitting at my computer, typing. The house is quiet, a ticking clock my only company, a steaming cup of Yorkshire tea at my elbow. And I am in my pyjamas. Someone is paying me to put words together into an enjoyable read.

Who am I? How do I deserve this? I am no one special, not really. Apart from an early aptitude for literacy, by age six I was reading books aimed at much older children. Shortly after that, I began crafting words. I have practiced writing my whole life but have very little formal training. I have no claim over the title of Freelance Writer.

Covid-19, 2020, and my family

When the pandemic hit, I was on paid parental leave, from having my 5th (and final) child. A job I had to pay bills. At 35 years old, I still had no idea what I wanted to do with my life. My husband was a contractor in IT, also a bill-paying job. New Zealand, our country, went into lockdown in March, and by April we were both unemployed.

We loved it! Not the deathly illness and overloaded healthcare systems, but the forced slow down. Having time at home with the kids was a gift to us. Nothing to juggle. My house had never been tidier, my laundry constantly up to date. I got over my fear of yeast and learned to make bread. The Great British Bake Off became my favorite show and, more importantly, I had time to watch it.

It was bliss. We were poor, but happy.

Then, in August of 2020, my husband had a freak medical event. He collapsed onto his leg and needed an emergency operation. The operation released a build-up of toxins, and he went into multisystem organ failure. For a week, he was on life support in ICU, then he developed secondary pneumonia in both lungs. He kept almost dying, and, because of the pandemic, I wasn’t allowed to see him.

Contemplating what might happen was impossible. Thinking about tomorrow was impossible. Forget day to day, I was minute by minute, second by second. Plastering a smile on my face for the little people looking to me to be their stable base.

Eight days after he went into the hospital, he finally turned a corner. Slowly, he healed. A month after I found him on the floor, he came home. Hobbling in on crutches, having lost over 35% of his body weight. Tears streaming down his face. Would our little girl, only seven months old, recognize him? When he came through the front door, she stared. Her tiny face a mixture of shock and disbelief. He was home. She refused to leave his side for days.

This experience changed our worldview, and we realized life was too short for nonsense. Too short for compromise. It can take one bad night to destroy everything.

A month after he came home, I enrolled in university. A month after that so did, he. We agreed. Two years living on benefits, scraping through on next to nothing, two years of hard grind, chasing the dreams we had both let fall away. Recalling our childhood imaginations; grand ideas, expert abilities.

Back to the beginning

My childhood dream was to be a mother. That happened before I was 20. My one claim to fame is raising pretty cool kids – if I do say so myself. They fill my house with chaos, laughter, fun and fights. They drive me to take long hot showers while contemplating how much it would cost to build a run outside. And, of course, I wouldn’t have it any different.

When my eldest daughter, now 18, was two, I attempted university; a Bachelor of Arts majoring in anthropology. I loved it but taking my daughter on trips to live in Uganda for three years while I studied local tribal culture seemed a bit extreme.

I switched to psychology, and that was good too. But then, within the space of a few months, my best friend moved overseas, my boyfriend and I split up, I found out I was pregnant (to ex-boyfriend) then lost the baby. I had a cancer scare. Then I totaled my car – don’t text and drive.

The car was the proverbial straw. My little blue Toyota Corolla, I still miss the curve of her hatchback, the way she took corners. She carried me through my full driver’s license test and was the only car my baby had ever been in. I had a pretty major mental health breakdown and dropped out of university. Ever since, career has eluded me.

In 2009 my dad asked me to help him with a business opportunity that had come his way; he needed someone to run it. For years, I worked in that company, and built it up to a stage where I had a decent income and staff. By this time, I also had three children and a failed marriage. But I purchased a house. Then, in 2016, Dad and I sold the company.

By this point I was in my early 30’s, feeling very unsure of myself. What did I have to show for myself? A bunch of kids. A house. A business, sure, but I wasn’t passionate about that. Nothing made me feel like I had made something of myself. Once my kids left home what would I have?

The nerd comes home

My husband and I going back to university after his near-death were a last-ditch effort for both of us. He went for audio engineering, and I went for my bachelor’s, picking educational psychology as my major.

It was like going home. Turns out I am a colossal nerd, a total teacher’s pet, the overachieving student that everyone hates. Reading my textbooks became my favorite Friday night activity. I lapped up learning with the unfettered joy of a kitten in a saucer of cream. Studying and writing essays rarely felt like work. And my lecturers seemed to like my writing. I stashed my A’s into a confidence bank and lifted my chin a little higher.

Then, just for fun, I did a creative writing course. Another childhood passion reignited, immersing people in a world of my creation. Crafting words into sentences that make readers feel, experience, and think.

I invested in my future author and bought the “writers toolkit” from Ultimate Bundle. In it was a host of resources about freelancing. Stories of mothers, college dropouts, people who turned a talent for word crafting into successful freelancing businesses. I thought, could that be me?

Tentative steps into Freelancing

I sank into the world of freelancing. YouTube videos, podcasts, blog posts, articles. And lots of thinking.

As a busy mum and university student, I knew I needed to be smart in how I approached this. I am good at overextending then burning out. To start with, I decided to just go with one platform; until I finished my studies. Finishing my degree is vital to me now. But it was Summer Holidays, the perfect time to devote myself to a project such as this.

There are so many different platform options; I looked at five, Fiverr, Upwork, Freelancer, People Per Hour, and FlexJobs. All these platforms have positives and negatives. My final decision was extremely scientific – I went with Upwork because I thought the green was pretty.

I spent several hours crafting my profile on Upwork, studying profiles created by top writers and reading more articles. To create a portfolio of works, I edited some university assignments. Then I began to scroll through jobs.

Being oriented towards child development and parenting, my interest was piqued by a job titled “Write journaling prompts for different ages”. I sent in my first bid at midnight and went to bed.

Everything I had read said that people usually have to bid for between 5-40 jobs before they landed their first one, so imagine my surprise when I woke up to find that this guy had taken my bid to the next level! After a short conversation, he offered me the job.

Victory! I danced around my living room, jumped on my coffee table and stamped my feet! Raced over to tell my husband. Someone was actually paying me to put words together. I have never been so excited about earning money before. In the end for that job, I worked for 6NZD per hour, but I didn’t care. It was awesome, it was experience, and he gave me a 5-star review. Then, a man wanting travel articles for around New Zealand hired me, I am still writing those articles now.