March 2024 marks my fourth year in business for myself and what a journey it’s been.
It is not four years of Jessica Reilly, Writer – that iteration came later. What my business looked like in March 2020 is very different than what it looks like today and thank goodness for that. But when I look back to the person who quit her job with only a semblance of a plan and a much bigger dream, I swell with pride for her. She was terrified but certain this was the path forward – and how right she was.
Hitherto, I had never done anything quite so impulsive. I did what I was supposed to – graduated high school, went to college, graduated cum laude, and started a 9-5 less than a week later. I got an apartment downtown and traveled for work and cried in my car about how mean my boss was. I dreamt of quitting and running away – to an ocean town or a mountain village, waiting tables and writing in the morning. But I stayed, wholly convinced in my inability to make it work in the chaos.
It wasn’t until I found the dream of van life in 2019 that things started to shift. I found an idea I couldn’t shake, a dream I returned to every morning when I was filled with dread at the prospect of going into the office. I kept it under wraps from everyone but my partner, who shared my desire for adventure. And when I took a small step forward at the start of 2020, the universe promptly kicked my ass through the door.
My plan was to freelance on the side while I worked my 9-5, to build up savings to buy a van while my partner and I renovated a duplex in the city. I landed my first client and soared with glee at the confirmation that I could do this. It was never in my mind to share my plans with anyone I worked with – but when I saw someone I knew from work while visiting my freelance client, I had to get ahead of it. When my boss told me I had to choose between the company and my client, I knew I only had one option.
When I left, everyone was surprised. I enjoyed the people I worked with, the travel, and the work I got to do for clients – but I dreamt of so much more.
I had said for years that I would never run my own business. I watched how much effort it was for my father to do the same, the trial and error, the second jobs, and the uncertainty in pay – and swore I would never put myself through that. But when push came to shove, I wanted to own my time more than I wanted a steady paycheck. (And it was a pittance of a paycheck, which made it easier to walk away. It’s not hard to replace a salary that low.)
My first client crashed and burned – and then my second client did the same. I found myself three months after leaving, floundering, alone, and isolated during quarantine. My partner worked in essential services and was called in to replace people who got furloughed, and I was left to my own devices for eight hours a day, five days a week.
The summer was a tough one for me. But when I finally embraced the truth of my dreams – to be a writer – things started to fall into place.
I got my first writing client in August and dreamt of being in a van in early 2021. But that didn’t come to fruition and again I found myself heartbroken, wondering what I was trying to do. It’s funny how you have to fail forward to find what’s meant for you. Instead of embarking on my nomadic adventure, I bought a business fundamentals course and niched my writing services down into cannabis.
The rest, as they say, is history.
No, it’s not – it’s still unfolding. Things did not magically get easier; I still struggled in business, had dry spells, took on bad clients, and made mistakes. I still struggled with demand avoidance, perfectionism, and time management. It will always be a work in progress.
But in these last four years, I have found a confidence in myself like never before. I have tried and failed and gotten back so many times I am no longer paralyzed by the prospect of making a mistake. I have stronger boundaries around every area of my life and I do not worry if I am overcharging for my services. I have put myself in situations where my only option was to succeed and I have. I have pushed myself beyond limits I thought were made of concrete only to find it was breakaway glass.
I own my time. I have complete control over what I do, the people I do it for, and where I do it from. I have made more money on my own than I ever would have staying at the agency I started at.
So here’s to the first four years and everything they brought me – and to the next four and everywhere I’ll go from here.
Highlights from the Past Few Years in Business
