I’d say I became a “professional writer” as a college student in 2008. I was an unpaid, one-story-per-week journalist for a local newspaper. It was just my first in a series of part-time freelance jobs, but it was exciting.
Nowadays, I’ve got it all as a freelancer: My own good-looking website with custom branding, high-paying clients and the ability to set my own schedule, a.k.a. take Mondays and Tuesdays as weekends, just because I feel like it. And did I mention a much higher income than my peers in similar corporate positions?
Yes, I feel endlessly lucky. But the truth is, it wasn’t always like this. Until three years ago, I was fully dependent on income from other full-time and part-time freelance jobs. Yes, I had my “alter ego” as a writer, but because I didn’t have savings to live off of while I built my business, I had to take on jobs that would pay the bills in the meantime.
Below, I’ll tell you about five of the side jobs I had over the course of those crucial six years in the buildup to starting my own business.
1. Night Security in College Dormitories
I have to admit: I won the lottery here. This was the dream job for a busy college student. I sat at the front desk of different dormitories from 10:30 p.m. until 4:00 a.m., and, for the most part, used the time to do my homework or write my weekly story for the local newspaper. I worked in single-gender dorms, which meant I didn’t have to deal with as much drunken partying, and the nights were quiet and easy. I only had to do rounds of the building once every hour, and the rest of the time I spent working on my writing.
2. Online ESL Teacher for English Teaching Academies
Sometime after graduation, I saw an ad for online English as a Second Language teachers that didn’t require previous experience. So, embracing the fact that I wasn’t getting a full-time job anytime soon (and forever happy with easy money), I applied to the job and got it. I was teaching English online via Skype to Japanese businesspeople at odd hours. It wasn’t ideal, but since I didn’t have a regular 9–5, I could deal with it and enjoy the extra income.
3. Content Writer for Outsourced Online Publications
With the realization that I wasn’t getting the “real job” I wanted anytime soon, I worked like crazy to get more and more articles published with my byline. For the first time, I was getting paid for freelance writing.
I wasn’t getting paid much, though, and was still doing job interviews any chance I got. But from those interviews, it became clear that I needed more experience, so I set out to get it. I found an internship overseas, in India, writing content for outsourced news publications. To be honest, I hated it, but it was a professional writing position that paid, and something that I knew would be a “wow” factor on my resume. I did it because I thought that afterwards, I’d be guaranteed a job. I was wrong.
4. Data Entry Specialist
This was a seasonal position, and by far the most boring job I’ve ever had. But with a solid seven months of work promised, which book-ended Christmas, it was a great source of predictable income. I had a steady paycheck, and because it was rather mindless, I had a lot of creative energy left over in the evenings and on weekends to invest in creating my “official” image online as a freelance writer.
One day at the beginning of December, I called in sick and stayed home to buy my domain name and set up a basic WordPress website with a free theme. It wasn’t pretty, but it was the turning point in going from a frantic sometimes-employed, sometimes-not “freelancer” to a serious, professional writer with a website to back me up.
5. From Content Writer to Chief Marketing Officer
After my data entry job ended, I started looking for ways to get experience in high-paid writing fields. I didn’t care what it was, as long as it was specialized and could lead to high profits in the long-term. To make a long story short, I’d made friends with a group of people who worked with a mobile app development company. They were proud of the work they did as developers and designers, but were embarrassed at how terrible the website copy was — it was so bad, they didn’t even want to list the company on their resumes. They encouraged me to apply for a job there, even though the “job” didn’t exist.
With nothing to lose, I tried anyway. The bosses were impressed with my portfolio, and after one interview, offered me a well-paid position to work on writing content for them. Two weeks later, I was promoted to Content Director, and six months after that, to Chief Marketing Officer.
This was a full-time gig, and I rarely wrote freelance pieces during this time. But I got some amazing experience that led me to officially starting my own company the next year after leaving that company for good.
6. On to Full-Time Freelancing
In April 2014, I quit my job working for the tech company and set out on my own. Because of all the things I’d learned over the previous six years as a professional writer and part-time worker, I was prepared to be my own boss 100 percent of the time and run my own business.
It was a long road “to the top” and full of detours, but honestly, I’ve yet to meet someone whose become a successful solopreneur who hasn’t had a similar story of taking on odd jobs that paid the bills.