Chapter 9

Freelance to Freedom

September 2014

At the end of the summer I got an email from someone who’d seen the videos I was posting on social media.

They wanted to connect me with a non-profit focused on education reform. The job initially seemed perfect, combining my skills in video, photography, and digital marketing. I showed up to their office every day, filming videos and creating marketing content, hoping this would be the turning point I desperately needed.

As the month progressed, Squarespace website jobs started rolling in too, and for the first time all year, I broke $5,000 in a month. 

For the first time in months, I felt like I was truly providing for my family. The weight on my shoulders lightened. It was a breakthrough, a sign that maybe, just maybe, I was finally on the right path.

With that small victory, I was able to get my car back on the road, pay my rent, and feel like I was living again. It was a fleeting moment of triumph, but it fueled my determination to keep pushing forward. Energized, I turned my focus to building out the Corporate Dropout Movie and set my sights on bigger goals. I envisioned scaling my projects to bring in $50,000 a month, imagining the stability and success that seemed within reach.

But just as things seemed to stabilize, reality struck again. I woke up to a $900 refund request from a client, pushing us further into financial turmoil. The high hopes and momentum I had built up crumbled, leaving me feeling defeated and questioning whether this was just another false start.

Three weeks into the non-profit consulting gig, the initial excitement faded. What started as a promising opportunity quickly began to feel like just another job—minus the benefits and security. The line between consultant and staff blurred, leaving me feeling boxed in and undervalued. The dream of freedom through freelancing was slipping away, replaced by the harsh reality of financial instability.

By Thanksgiving, the non-profit ended my contract, and our finances were once again in dire straits. Dinner with my old church family turned sour, riddled with questions about my faith. "Is he Rastafarian? Are you Muslim now?" they asked, as if my entire identity was up for scrutiny. The weight of their questions added to the strain I was already feeling in every aspect of my life.

At home, the tension was at an all-time high. Arguments with Juliana grew more frequent, both of us too exhausted and stressed to offer each other any comfort. My mother’s patience was wearing thin, her frustration bubbling over into sharp words and tense silences. I could feel the pressure building, the sense of failure looming over me like a dark cloud.

"I'm not going to be here past February," I declared one day, unable to bear the constant stress and uncertainty any longer. But even as I said it, I wasn’t sure how I was going to turn things around.

December 2014: Hitting Rock Bottom

When December arrived, I was desperate for a change. Another artist friend reached out, wanting to go to Jamaica to shoot a couple of music videos. The offer was tempting, a chance to escape the suffocating reality of my life. Even though I was broke, I couldn’t turn down the trip. The weed was abundant, and the whole experience felt like a surreal escape from the struggles I faced at home. But by the time I got back, reality hit harder than ever.

It was Christmas season, but there was no joy in our home. Financial despair had fully set in. I was tired of short-changing myself for "exposure," yet I couldn’t see a way out. By the time Shiloh’s first birthday rolled around on December 28th, we were so broke that we couldn’t afford anything beyond a simple cake his grandmother brought.

The sight of that lone cake on the table broke something inside me. I was supposed to be the provider, the protector, yet here we were, barely scraping by. It was a somber celebration, to say the least.

I moved to my spot on the living room floor next to the computer, headphones on, getting lessons from a guy in San Diego on how to write sales copy. I was desperately trying to unlock new ways to generate income, but the strain was taking its toll. I wasn’t angry—I was mad, insane with desperation, grasping at anything that might pull us out of the hole we were in.

The bubble of do what thou wilt had collapsed. I was stuck, watching my dreams slip further out of reach. The fights with my mom peaked during that winter, her frustration hemorrhaging financially over my struggles. In one year, my income plummeted from $78,000 to $18,000. It was like we were in free fall.

My income had plummeted drastically, and I knew I needed a sustainable system to pull us out of this mess. But where do I start?