From Side Hustle to Main Meal: How Nicaila Matthews Okome Scaled Her Passion Project

From Side Hustle to Main Meal: How Nicaila Matthews Okome Scaled Her Passion Project

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: Why side hustles can be a smart career safety net How to know when a side project is ready to grow The difference between hobbies and businesses Building a brand while holding a day job How to manage your time for real progress without burnout 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.

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The AARP CEO's Playbook for Staying Competitive After 50

The AARP CEO's Playbook for Staying Competitive After 50

We tend to talk about AI and the future of work as a young person's game. Dr. Myechia Minter-Jordan, CEO of AARP, is here to challenge that notion. A physician turned healthcare executive turned nonpr...

29 Kesä 29min

Why Nobody Feels Financially Secure Anymore

Why Nobody Feels Financially Secure Anymore

“It’s not your fault.” This is the message Alissa Quart has spent over a decade trying to get people to believe when it comes to economic hardship. Right now, it feels harder than ever to embrace. Al...

22 Kesä 28min

Most Companies Are Built to Fail Their Mission. Here's the Fix.

Most Companies Are Built to Fail Their Mission. Here's the Fix.

We've built an economy that rewards destroying value. Eric Ries wants to know how we got here, and whether we can build our way out. Eric wrote The Lean Startup in 2011 and helped define a generation...

15 Kesä 26min

Lessons From a Year of Letting AI Do Everything

Lessons From a Year of Letting AI Do Everything

Joanna Stern spent a year using AI to do (almost) everything: write her emails, analyze  her medical records, text her wife, drive her around, and even fold her laundry. The result is her new book, I ...

8 Kesä 29min

Jenny Hagel on How to Build a Creative Career When the Odds Are Against You

Jenny Hagel on How to Build a Creative Career When the Odds Are Against You

Comedy writer Jenny Hagel has six Emmy nominations. The other week, she wrote 20 jokes. One made it to television. She doesn’t see this as failure, though. It’s the nature of the job. And it might off...

1 Kesä 28min

Bonus: Lesbian Bars and the Secret Formula for Belonging

Bonus: Lesbian Bars and the Secret Formula for Belonging

Lesbian bars aren’t just nightlife, they’re evolving spaces of community and chosen family, and they have a special place in Jessi Hempel’s heart. On this bonus episode, Jessi sits down with one of He...

28 Touko 15min

How to Build a Career You Actually Believe In

How to Build a Career You Actually Believe In

We're trained to climb ladders and chase titles, but what if the real metric of career success was the positive impact you have on the world? In this episode from the Hello Monday archives, host Jessi...

25 Touko 29min

We're Lonelier Than Ever. Ritual Is the Answer.

We're Lonelier Than Ever. Ritual Is the Answer.

Rituals work. They help us make meaning, process transition, and connect with each other. That’s why we’ve been doing them for more than 300,000 years. So why, in this century, have we largely abandon...

18 Touko 28min

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