The Secret to Scaling a Side Hustle Without Burning Out

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Lessons from Side Hustle Pro's Nicaila Matthews Okome

I’ve always had a side hustle. I think a lot of us do. For me, it’s been writing projects, usually executed before sunrise. There are two reasons I keep that second hustle alive: one is practical—if I ever get laid off, I’ll have something to fall back on. The other is more personal—I want my work to matter. Side hustles often let us explore new possibilities without burning everything down.

This week on Hello Monday, we revisit one of my favorite conversations from the archive. You'll find that it's even more relevant today than it was when we first published it. Our guest is Nicaila Matthews Okome, host of Side Hustle Pro. It's a podcast that spotlights Black women entrepreneurs who’ve turned side projects into full-time ventures.

Nicaila didn’t set out to be an entrepreneur. She worked hard to meet the expectations that many high achiever cultivate in young adulthood. Her early career was a testament to that work with an MBA from Michigan and roles at companies like Google and NPR. But while her résumé projected stability, she was quietly experimenting. Testing. Asking: Is there something more meaningful I could build?

Eventually, her podcast—originally a side project—became the answer.

In our conversation, Nicaila explains how you know when your project is ready to grow, how to make smart use of limited time, and how to tell the difference between a hobby and a business. She also offers my favorite piece of advice: Don’t tell yourself no. So many of us pre-reject ourselves before anyone else gets a chance.

You can find the episode here:

Join me this week for Office Hours!

We’ll be taking this conversation to Office Hours this week. You can find me and senior producer Sarah Storm right here on Wednesday afternoon at 3pm EST. We'll talk about the episode...and anything else that's on your mind!

Hello Monday is LinkedIn News’ weekly podcast about the changing nature of work—and how we must change to keep up. It's hosted by me, Jessi Hempel. Subscribe to the show's newsletter.

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