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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

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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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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

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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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Most people think quitting is the story. It isn’t.

Before people leave their jobs, something usually happens first. A pause. A realization. A moment that makes it impossible to keep going the same way. Five years ago, Dr. Anthony Klotz coined The Great Resignation. But the real story was never about quitting. It was about clarity.

In the Season 5 premiere of Why I Left, Anthony returns to unpack what actually drives career change. Not slow dissatisfaction. Not calculated pros and cons. But jolts. Sharp moments that disrupt how we see our work and ourselves.

Anthony is an organizational psychologist at UCL School of Management and author of the upcoming book Jolted. We explore the six types of jolts that shape careers, the rise of reluctant stayers, the hidden cost of return-to-office mandates, and how AI may trigger the next wave of career reshuffling.

If you have ever felt a sudden shift at work. If you have questioned whether you still belong where you are. If you are navigating a pivot or protecting your wellbeing in a tight labor market. This conversation is for you.

Press play.

Enjoy!

Stay connected with Anthony Klotz

Website: https://anthonyklotz.com/

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

Purchase Jolted: https://anthonyklotz.com/the-jolted-book

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

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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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After 100 episodes, one truth stands out. Leaving is rarely about quitting. It is about alignment.

In this season five launch, Brian Aquart reflects on what a hundred conversations with leaders, founders, and operators have revealed about career transitions and identity shifts. What changes when success no longer fits. What it costs to stay too long. And why discipline, not momentum, builds something that lasts.

This season is for anyone at a crossroads. For executives recalibrating their definition of success. For builders questioning the path they chose. For professionals who know something needs to change but cannot yet name it.

If you have ever wondered whether leaving means failing, this season reframes the question entirely.

Enjoy!

Stay connected with Why I Left
Visit: https://www.WhyILeft.co

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

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/

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On the Season 4 finale of Why I Left, Brian sits down with Craig Whitely, better known as Craig the Barber, who shares his inspiring journey from the world of finance to becoming an award-winning barber and founder of Burke Avenue, a premium mens grooming line. Discover how a passion for barbering, ignited by a simple gift from his father, led Craig to leap from bankings rigid structure to entrepreneurship, building a trusted brand recognized by Mens Health.

Craig opens up about overcoming fear, the power of intentionality, and the importance of listening to consumers. Whether youre eyeing a major career pivot or striving to build a brand that truly stands out, this episode delivers invaluable lessons on resilience, personal fulfillment, and doing it your way. Dont miss Craigs practical advice for reinventing your career and thriving in a competitive industry!

Enjoy!

Stay connected with Guest

Website: https://www.burkeavenue.com/

YouTube: https://www.youtube.com/craigthebarber

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

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

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Visit: https://www.WhyILeft.co

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

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

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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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Brian sits down with Jordana Cole, founder of Ignited LLC. Jordana shares her courageous decision to leave behind a successful corporate career and follow her passion for igniting leadership and transformation. Discover how her trailblazing path, from breaking barriers in her hometown to leading learning and development initiatives, helped her find her true calling.

Jordana reveals the challenges and rewards of entrepreneurship, her philosophy on intentional, everyday leadership, and the importance of aligning passion with profession. Plus, get a sneak peek at her upcoming leadership book and actionable advice for anyone considering a bold career move. Dont miss this episode filled with insights, real stories, and practical tips to help you spark positive change in your journey!

Enjoy!

Stay connected with Guest

Website: https://ignitedbyjordana.com/

LinkedIn: https://www.linkedin.com/in/jordana-cole-mapp-pcc-a8445a8/

Stay connected with Why I Left

Visit: https://www.WhyILeft.co

Subscribe:

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

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

Follow:

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

Why I Left is happy to be part of the Alive Podcast Network, which offers a diverse range of shows featuring powerful storytelling, insig

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/

Send a message to the show

Brian sits down with Lori Eberly, founder of Radius Executive Coaching and co-author of "Fuckery." Lori shares her compelling journey from hospice social worker to leadership development expert, revealing how grief, transition, and trust shape meaningful career change. Discover practical, neuroscience-backed strategies for navigating loss in your professional life, building resilience, and transforming team culture.

Loris trauma-informed approach provides actionable insights on overcoming toxic workplace habits and fostering authentic connections. Whether you're considering your next career move or leading through change, don't miss this conversation packed with wisdom, humor, and real-life advice for making bold, intentional decisions. Check out the episode for inspiration to trust yourself, grieve what you leave behind, and step forward with clarity.

Enjoy!

Stay connected with Guest

Website: https://www.radiusecd.com/

LinkedIn: https://www.linkedin.com/in/lori-swartz-eberly-msw-lcsw-licsw-74550964/

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

Why I Left is happy to be part of the Alive Podcast Network, which offers a diverse range of shows featuring powerful storytelling, i

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/