Millions of professionals are balancing side hustles alongside their full-time jobs. But what does it take to turn that extra project into something bigger? In this episode from the Hello Monday archives, Jessi Hempel sits down with Side Hustle Pro creator and host Nicaila Matthews Okome to explore how side work can lead to a meaningful, lasting career.
Nicaila didn’t always see herself as an entrepreneur. She built her résumé with big-name employers, earned her MBA, and followed a traditional career path. But she kept testing new ideas on the side — and eventually turned her podcast into a full-time business. Now, she helps others navigate the same transition.
If you’ve ever dreamed about turning your passion project into something more, this conversation is for you.
Jessi and Nicaila discuss:
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Why side hustles can be a smart career safety net
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How to know when a side project is ready to grow
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The difference between hobbies and businesses
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Building a brand while holding a day job
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How to manage your time for real progress without burnout
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What stability looks like when you’re your own boss
Nicaila also shares her journey from NPR and Google to building Side Hustle Pro, a thriving platform for Black women entrepreneurs.
Keep the conversation going at Hello Monday Office Hours. Join us on the LinkedIn News page this Wednesday at 3 PM ET.
