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A Transparent Look At My Journey Into Freelancing

Middle-class privilege

I’ll start by saying that it absolutely takes a certain level of privilege to take the risks involved with starting an entirely new career path with no backup plan or cushion to fall back on.

Celebrating mediocrity

Growing up, I excelled in school. Not because I was smarter than anyone, but because my parents made me. They threatened me, so I studied. When I got good grades, I was rewarded. It was a simple system to understand.

Failure and more failure

I got my first full-time marketing job, one week after I graduated from college. I didn’t even apply. A colleague from my part-time university job, referred me to an open role at a company her husband worked for. I did one interview, and a few days later they hired me. After three years and the harsh realization that there was zero room for growth at this company, I handed in my two-week notice. Later that year, I traveled to Europe for three months and spent six weeks on a cross country road trip.

Every rejection was a punch to the gut and a blow to my ego.


After my failed job search, I decided to give freelancing a shot. At the time, I had no savings, a negative bank account, more than $20,000 in credit card debt and over $50,000 in student loans. In 2018, I bought a one-way ticket to Bali for $500 on my credit card and maxed out my cash withdrawal on another credit card.

Let’s talk numbers…

In my first full year of freelancing, I made $16,000.


Taking risks is not for the faint of heart. But once you push past the discomfort and inevitability of failure, serious growth happens. Past versions of me refused to recognize my immense level of privilege I had (and still have). I sank into the role of the victim and blamed everyone around me for my lack of success.


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