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When your boss finds your side hustle, what do you do?

Nicaila Matthews Okome received the “We need to talk” email while working at NPR. HR got involved. Screenshots were printed. Her ambition was suddenly under scrutiny. That moment forced a decision: shrink or build.

Nicaila is the founder of Side Hustle Pro, a top-ranked entrepreneurship podcast with over 10 million downloads. But before the Hall of Fame recognition, it was a strategic side hustle. She did not quit in anger. She built revenue streams. She studied sponsorship models. She saved aggressively. Over 18 months, she created an exit plan and left corporate on her terms.

In this episode, we talk about what it really takes to bet on yourself. How to build the “create your own opportunities” muscle. Why side hustles are training grounds for ownership. And why you should never leave while you’re confused.

If you are navigating tension at work, building something quietly on the side, or wondering whether it is time to pivot, this conversation will challenge how you think about readiness and risk.

Enjoy!

Stay connected with Nicaila Matthews Okome
Website: https://sidehustlepro.co
LinkedIn: https://www.linkedin.com/in/nicailamatthewsokome
Training: https://sidehustlepro.co/freetraining

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Your story deserves to be told with clarity and impact. That’s why I created Storyline by Kingswoodto help executives, founders, and rising leaders align their presence with their next chapter.

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Stephen A. Hart left a six-figure corporate leadership role after doctors warned him about the physical toll of chronic stress. What looked like success on paper was quietly becoming unsustainable.

In this conversation, Stephen shares how burnout, high blood pressure, and a cardiologist’s warning forced him to confront what his career was really costing him. He opens up about turning down a six-figure safety net, betting on himself, and building a purpose-driven business rooted in legacy and impact.

Then the mic flips.

Brian reflects on what 100 resignation stories have revealed about fear, authenticity, and leadership in a changing world.

If you are navigating burnout, questioning your next move, or wondering what courage actually looks like in real life, this episode is for you.

Enjoy!

Stay connected with Stephen A. Hart
Website: https://stephenahart.com
LinkedIn: https://www.linkedin.com/in/iamstephenahart/
Blu Oak Marketing: https://bluoakmarketing.com/

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Storyline by Kingswood helps leaders and professionals make sense of career transitions, identity shifts, and the stories they’re telling about their work.

Learn more: https://drive.google.com/file/d/1yWlc-4M5JIaTMPurQlcccQ8gZF5lEabY/view?usp=sharing

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Thanks to our partners & sponsors:

BetterHelp: This episode is sponsored by BetterHelp. Give online therapy a try at https://betterhelp.com/whyileft and get 10% off your first month

ApodcastGeek: Use Code BA10 to 10% off your first order at https://apodcastgeek.com/

Your story deserves to be told with clarity and impact. That’s why I created Storyline by Kingswoodto help executives, founders, and rising leaders align their presence with their next chapter.

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Interested in sponsoring Why I Left?

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Loneliness at work is rising. And it is a structural issue.

In this episode, Tracy Brower, PhD, returns to Why I Left to unpack the growing disconnection inside modern organizations. Fifty percent of people globally report feeling lonely. Leaders feel stretched thin. Teams feel unseen.

Tracy is a sociologist and Vice President of Workplace Insights at Steelcase. She has spent years studying happiness, belonging, and the future of work. In this conversation, she explains why trust is built through consistency, why visibility is not the same as presence, and how culture is defined by the worst behavior it tolerates. She also shares insights from her new book, Critical Connections, unpacking how hustle culture, distraction, and performative presence erode trust and belonging.

If you lead people, this episode will challenge how you think about productivity, accountability, and connection. You will walk away with practical shifts you can make immediately.

Enjoy!

Stay connected with Tracy Brower

Website: https://tracybrower.com

LinkedIn: https://www.linkedin.com/in/tracybrowerphd/

Purchase Critical Connections: https://www.porchlightbooks.com/products/critical-connections-tracy-brower-9781394362264

Work with Brian

Storyline by Kingswood helps leaders and professionals make sense of career transitions, identity shifts, and the stories they’re telling about their work.

Learn more: https://drive.google.com/file/d/1yWlc-4M5JIaTMPurQlcccQ8gZF5lEabY/view?usp=sharing

Stay connected with Why I Left

Visit: https://www.WhyILeft.co

Subscribe:

YouTube: https://www.youtube.com/channel/UCMgQI4X0kEp8-o7Z9D3tRmg

Apple Podcasts: https://podcasts.apple.com/us/podcast/why-i-left/id1613667100

Spotify: https://open.spotify.com/show/0TE4Y626idPxNeewpCG6Ef

Follow:

Instagram: https://www.instagram.com/officialwhyileft/

LinkedIn: https://www.linkedin.com/company/why-i-left/

Connect with Brian: https://www.linkedin.com/in/brianaquart/

Rate us 5 stars and share feedback: https://podcasts.apple.com/us/podcast/why-i-left/id1613667100

Your story deserves to be told with clarity and impact. That’s why I created Storyline by Kingswoodto help executives, founders, and rising leaders align their presence with their next chapter.

Support the show

Interested in sponsoring Why I Left?

Learn more about partnership opportunities here: https://whyileft.co/sponsor-why-i-left-podcast/