SEASON 2

The Side Hustle Series

Find inspiration for your side hustle. Listen to how folks selected, launched, managed, and transitioned their side gigs into their main thing.

Second Breaks is a show where we explore what it takes to navigate this changing world and thrive in our careers.

September 5, 2019

Prioritization and discernment are two important skills you must master when you have a day job and a side-hustle. When you only have an hour or two and that’s all you have for that day, you have to focus on something that’s really going to move the needle forward. CEO/CTO Susan Boles shares how she manages to juggle all the balls in the air.

September 12, 2019

While in college, Althea Wiles discovered that working around flowers was her dream job. Not simply as a florist helping build someone else’s business. She wanted her own floral business. But Althea was (is!) practical. She knew she needed the runway to build her experience and her business from the ground up.

September 26, 2019

John Lagoudakis was looking for an alternative way to make a living. One that earned enough to support his family and gave him the flexibility to spend time with his young kids. He stumbled upon a book that turned his beliefs about time and money upside down and paved the way to his new career in digital marketing.

October 3, 2019

Justine Sones had already established herself as a licensed massage therapist when she started considering the idea of location-independent work. Finding out that she was pregnant just made her more serious about exploring other options. When she saw a random request on Facebook for social media marketing help, she raised her hand. Leaning into the skills she had honed in her massage therapy work, she grew this small side-job into something more expansive and the basis of her new career as a business strategist for mom entrepreneurs.

October 10, 2019

You can speed up financial independence with a side-hustle, but you have to start with an intentional approach and take smart steps toward your goal. Kim, who writes at The Frugal Engineers, shares her and her husband’s journey, how they achieved financial independence and how they transitioned from corporate employment to self-employment debt and mortgage-free.