When Is It Time To Leave Your 9-5? Overcoming fear, Knowing When it is Right for You, and How to Get Started

Posted on February 26, 2022

When do you know it’s time to be your own boss? Time to turn your side hustle into your only hustle? Social Siren Marketing owner, Jessica Riedy, and Amanda Cowart, owner of Lemon Zest Copywriting, discuss how they knew when to pivot. They also talk about turning doubt and fear into positive forces towards successful entrepreneurship.


When is it time to turn your side hustle into your only hustle? Jess and Amanda compare the journeys that led them to their respective small businesses.

Amanda started her company, Lemon Zest Copywriting, 6 short weeks ago. Her background was copywriting for clients, then she was employed as an in-house copywriter for a school. She thrived. Then, she moved with her family to the Northwoods and didn’t know what to do. Amanda took a job at a local Chamber Of Commerce and, initially, it was a great way for her to meet people in her new community. But the job became so stressful that her emotional, mental, and physical health suffered. Amanda had a secure, stable job that left her unwell. Without another job lined up, she gave notice and left. She had the support of her husband, they had money set aside, and so she decided to move forward and take on clients independently as a professional copywriter again.

Jessica had a job that wasn’t terrible, but it wasn’t challenging, and she wasn’t learning anything new. For her personality, that’s significant. She felt stagnant. Having one day follow the other with nothing different was depressing and the lack of challenges made her feel like a failure to herself. Her side business made her feel excited and inspired. She wanted that to be her norm. Jessica did not have a nest egg set aside, but like Amanda, she had the full support of her husband. And she’s always been something of a risk taker. In 2017, she left her 9 – 5 job and turned her social media marketing company into her only job.

But, how do you know when it’s time for you to take a leap? Where do you find the support you’ll need if you don’t have a significant other?

No doubt business owners live on a rollercoaster of high highs and low lows that can get scary. That’s okay. Mistakes will be made. Lessons will be learned. Lean into the discomfort of the unexpected to figure out strategies to prevent future issues. If you can’t change something negative, find a way to reframe it.

As a friend of Amanda’s said, “I’m afraid to take this new job and that’s why have to take it.”
Imposter syndrome, those “What if…” questions, and why you need to show confidence from the start. Lots to listen to!

References and Links:

Social Siren Marketing

The War of Art: Break Through the Blocks and Win Your Inner Creative Battles by Steven Pressfield