Olivia Carr is an entrepreneur and business leader who spent more than a decade building the luxury brand "Shhh Silk" from a spare room into an eight-figure global business. She walked away from the company at age 44 and is now working as a corporate advisor while turning her work with women in midlife into her upcoming book, Midlife Unfiltered. Through The Midlife Truth Project, she is working to create systemic change in workplaces and give midlife women greater space to be heard and supported.
In today's episode, Olivia joins me to discuss her decision to walk away from her eight-figure global brand at 44 and rebuild from zero income.
Olivia shares how she realized that the business she had worked so hard to build no longer fit the life she wanted. She also opens up about the internal shift that made her question her definition of success, the role of perimenopause, and what it felt like to walk away from her financial security.
We dive into how to recognize when you have outgrown a career, business, or version of yourself. Olivia explains how midlife and perimenopause changed her tolerance, priorities, energy, and relationship with success, and why women need to pay attention when their internal definition of a rich life begins to change.
The conversation also covers Olivia's Midlife Truth Project and the witness conversations she has been having with women around the world. She explains why women often need to be truly seen and heard rather than fixed, and how creating a safe space can help women reconnect with their voice and what they truly want.
Join us today as we dive into recognizing when your life no longer fits, redefining success in midlife, preparing financially for a pivot, navigating business grief, creating psychological safety at work, being truly heard, building a supportive community, and much more.
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Want a space to talk openly about where you are in midlife?
Book a witness conversation with Olivia Carr to be heard, reflect on what's really happening in your life, and start making sense of your next chapter.
Book your conversation with Olivia:
https://www.oliviacarr.com.au
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Want to understand what women are really experiencing in midlife?
Explore Olivia Carr's Midlife Truth Project for honest conversations that bring visibility to the challenges around identity, energy, work, and this major season of change.
Learn more about The Midlife Truth at:
https://www.oliviacarr.com.au/pages/the-midlife-truth
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If this episode lit something inside you, that quiet knowing that you're meant for more, then I want to personally invite you into the most powerful room of the year.
ReLaunch To A Rich Life LIVE is a transformative, neuroscience-backed 3-day experience happening September 17–19, 2026 in Scottsdale, Arizona. It's designed for women who are done playing small and ready to step into clarity, confidence, and next-level success, not just in business, but in health, wealth, relationships, and life.
This isn't another event, it's a quantum upgrade into the life you're meant to live. Join women who are ready to rewire their identity, elevate their frequency, and claim a Rich Life that feels as good on the inside as it looks on the outside.
Learn more and join us in September:
https://relaunchtoarichlife.com
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Visit Olivia Carr's website:
https://www.oliviacarr.com.au
Connect with Olivia on:
Instagram: https://www.instagram.com/the_olivia_carr/
LinkedIn: https://au.linkedin.com/company/olivia-carr-advisory
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Connect with Hilary:
Website: https://therelaunch.com/
Instagram: https://www.instagram.com/hilarydecesare/
Facebook: https://www.facebook.com/TheReLaunchCo
Interested in being a guest on the ReLaunch Podcast or booking Hilary as a guest? Email us at [email protected]
Find Us on Your Favorite Podcast App:
https://the-silver-lined-relaunch.captivate.fm/listen