“I Decided To Be My Own Boss.” How Gregory Littley Prioritized Career Growth Over Job Security

Have you ever wanted to ditch your corporate job?

Content creator Gregory Littley once did, too. But he wasn’t quite sure how to go about it. The NYC-based digital strategist loved his paycheck, but loathed his work life — and ultimately abandoned his corporate job to become his own boss. Here’s how he did it.?

Littley had previously worked at some of America’s largest corporations: L'Oréal , Revlon , Ford , Walmart , The New York Post , and more. After years of collecting corporate paychecks, Littley was disillusioned. He felt he’d lost his creative edge, as well as autonomy over his own work, and was ready for a change.?

“The payoff was strange and bizarre,” Littley said. “I was making money but I actually felt quite awful. I didn’t have full autonomy or control over who I was working with. I really started to understand that full-time employment wasn’t the safest place for me. I was focused so much on this false sense of security that I believe corporations gave me.”

At first, Littley struggled to unplug from his corporate workflow.?

“I kept convincing myself that I absolutely needed a full-time job,” he said.

But there would be a breaking point. After abruptly being let go from one corporate job amid the COVID-19 pandemic, and then being stifled on a creative project at the next, Littley knew it was time for a change. In 2021, he made the leap into freelancing full-time.?

“I decided to be my own boss and that changed everything,” Littley said. “I really had to figure out what did freelancing on my own look like? I was terrified of how I was going to make money.”

Littley quickly got to work at cementing his brand. He’d rebound, landing a gig directing his first major freelance ad campaign with the Smarties Candy Company . Finally unfettered, he unleashed his creative spirit in full force — and it paid off. The campaign was a smash hit. For the first time in his life, Littley felt like he had the keys to his career. All he had to do was hop in the driver’s seat.?

It was here Littley had a crucial epiphany: corporate job security was a mirage — and clinging to it had nearly derailed his life.

“Nothing would have changed if I hadn’t realized I didn’t need to be employed by a big company for my ideas to matter,” Littley said. “It was a really freeing moment to come to the realization and the understanding that so many things that I thought were provided to me by corporations and companies were things I could figure out and provide for myself. I was focused on this false sense of security that I believed corporations gave me. It’s very easy to fill your head with scary thoughts about what it is like to be on your own.”?

Since becoming a career freelancer, Littley also co-founded PA?RDE? Beauty , a LGBTQ+-owned beauty products line. This year, he’s worked on digital product roll outs for both Meta and Pinterest , and has led other creative projects for clients like H&M and Amazon .?

“From there, I kind of felt like the sky was the limit,” Littley added.

Did you ever quit your job to become your own boss? How did you do it? Let us know in the comments.?

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Written by Dorian Geiger