At age 18, I made the decision to fund my college education through debt. In hindsight, it was a horrible judgment call. The loan accrued five figures of interest — and a life of its own — before I graduated college. It almost stopped me from pursuing my dream of attending graduate school — but it didn’t, and instead I funded my way with a mix of savings, fellowships and income.
But back then, now almost 13 years ago, I was convinced that my education was the best possible investment I could make in myself — that when I turned 22, I would get a high-paying job, thanks to attending a competitive undergraduate school, and working hard.
My dreams did not reflect reality.
Following a different career path
I entered the workforce buried under student and medical debt. While I was fortunate enough to receive three job offers at graduation, there was no entry-level salary in the world that was going to enable me to live sustainably in light of my debt.
I didn’t know how I was going to crawl out of my self-inflicted, upside-down financial situation. The only solution I saw was to make more money, so I hopped on Craigslist and poked around for side gigs. It was there that I came across the words “freelance writer.”
Eight years and tens of thousands of hours of labor later, I run a small business, Storyhackers, with my husband. Working with a team of 28 storytelling consultants, we have helped economists, Fortune 500 companies, high growth companies, corporate innovation teams and organizations focus on doing good in the world. We are now building our first products using the methods we created.
I had made a big mistake with my money at a young age. But there was a path for me to escape, leading me from financial insecurity to empowerment.
Enter the side gig
It wasn’t as if I had a master plan as to how to start this company. I liked my job as a manager in the tech industry. My then-boyfriend knew he wanted to run a company one day, but never imagined that he’d be running one like ours — and so soon in his life.
But there was no glamour involved with the first steps to getting here — just an ability to put up with a lot of criticism, a willingness to work hard and a tolerance for both earning peanuts and having no social life throughout my 20s and early 30s.
How did I start? I loved literature. I published my first poem in an anthology when I was only 11, and could speak four languages before I turned six. I studied writing and made it my focus from grade school through college. At night, on the weekends and in every moment that I had away from my full-time job (including my train commute), I worked on the “unnamed side thing” because it didn’t feel like work, and it was helping me pay down my debts.
By the time I quit my job to make this hobby my career, I was making about $50K on the side. That number showed signs of growth within my first several months. Six months later, I had a co-founder. A year later, that co-founder became my husband.
Want to build a side business of your own?
Almost a decade later, here are the most important lessons I’ve learned. Keep in mind that every entrepreneur’s story is different, so take them with a grain of salt:
- Let your employer know. I had early, open and honest conversations with both HR and my bosses, and promised to never compete with our company and their work. Nobody ever questioned my work ethic and, during the time I was running my side-company, I received two promotions that more than doubled my salary over a period of three years. I ended up staying with the company for almost five years, and left them with two “capstone” projects that are still in use, and generating financial value, four years later.
- Take small steps. When I started my freelance practice, I had such severe imposter syndrome that I refused to use the words “entrepreneur” or “founder” to describe myself until about 2015 or 2016 — when I had already been one for five years. The difference that I perceived between myself and a “founder” seemed too far. Despite this self-doubt, I kept trying. A million tiny steps and many fumbles later, I woke up one day as the co-founder of a company.
- Immerse yourself in industries that you know well. Successful companies know how to cater to the needs of their customers. More important than the product or service that you sell is an understanding of how it makes others’ lives better. By researching and getting to know the industry that you’re targeting, you’ll have a much more straightforward time marketing to your first customers.
- Consult with an attorney and CPA as soon as possible. Yes, you’re looking at an upfront investment of at least a few hundred dollars, but that will be worth it in the long-term. For instance, I paid about $2,000 for the contracts that Storyhackers still uses today. I paid close to $1,000 a year for a CPA. These decisions have minimized hiccups for both myself and my co-founder.
Discipline is key, and a strong work ethic is a must. Some days are going to feel more stressful than you can fathom. Rejections are going to hurt. But if you practice taking tiny steps, progress will eventually come in the form of bigger leaps. Embrace failures, and expedite your learning by studying the paths of others.