What if the very struggles that kept you up at night—the setbacks that threatened to break you—were actually the spark meant to launch you into a life richer and more purposeful than you ever imagined? Have you ever considered that the obstacles you’ve faced might be shaping you for something bigger, something uniquely yours?

This week’s episode is a powerful reminder that our toughest journeys can become our greatest testimonies. Meet Ashley Kirkwood: entrepreneur, powerhouse speaker, and a mentor to women carving out lives of meaning, fulfillment, and significance. But beyond the accolades and multi-million dollar business, Ashley’s story is about so much more—it’s about the courage to acknowledge your scars and use them as stepping stones, not stumbling blocks.

Ashley doesn’t shy away from sharing the real, unfiltered moments: the pain of feeling unseen as a child, the sting of bullying, and those chaotic seasons where ambition and burnout collided. She gets honest about the challenge of balancing business with being present for family and faith, and how leaning into those honest, sometimes uncomfortable, conversations changed everything.

But this isn’t just a story of overcoming—it’s an open invitation. Ashley’s journey is living proof that our wounds and worries don’t disqualify us; they refine us. By letting go of perfection, choosing healing over hustling, and letting faith call the shots, she transformed fear into bold confidence and became a champion for other women to do the same.

If you’ve ever wondered if the messy parts of your story could find a place in your purpose, Ashley’s words are here to encourage and empower you. All those late nights, disappointments, or detours—they can become the richest soil for growth if you let them. You’ll hear how setting boundaries, cultivating soul-level confidence, and believing you are worthy of your dreams can lift you—and those around you—even higher.

Timestamps:

00:00 Ashley: Inspiring Representation and Success
10:05 Prioritizing Family Time
12:01 Bridging Understandings in Law Careers
19:04 Overcoming Fear and Hardness
26:30 Beware of Powerful Snares
27:26 Fearless Guidance for Influencers
34:02 Unresolved Grief and Closure Transformation
42:29 Commitment and Purpose Over Adversity
47:42 The Importance of Setting Boundaries
49:42 Embrace Rest for Renewed Strength
58:35 Imperfect Lives and Overcoming Struggles
01:01:29 Holistic Life Planning Essential
01:06:02 Embrace “Yes” Beyond “No”
01:11:45 Connect for Free Business Resources

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#WorkLifeRhythm #EmpoweredLiving #DreamChasers #OvercomingFear #PurposeJourney #PurposeOverProfit #LeadWithFaith #PurposeInAction

About the Guest

Ashley Kirkwood is an entrepreneur, speaker, and award-winning lawyer. As a renowned corporate attorney, she reached what many would call a peak – a $300k+ job. But she left it to go on her own.

She began a virtual law firm, which quickly replaced and then surpassed her previous income. But along the way, she realized two things: she loved speaking and teaching, and she also had a real talent for scaling up a business. She perfected packaging and presenting professional services to corporations and other organizations, and started teaching others. Speak Your Way to Cash® was born.

Ashley’s enthusiasm and success mindset are infectious, and her results have been well-documented. Most important to her, however, is how her teachings help, inspire, and empower others. Professionally, that’s what she lives for.

Ashley has been recognized as a thought leader by FORBES, Crain’s Chicago Business, Black Enterprise, The Chicago Tribune, and more.

Ashley invites listeners to DM her the word “summit” on Instagram to receive a link to her next free event about selling services to corporations.

Connect on Instagram: @theashleynicoleshow

She encourages interested listeners to join the Speak Your Way to Cash Facebook group, a free resource for entrepreneurs, experts, and speakers.

Speak Your Way to Cash Live (October Event)

Learn more and sign up: Speak Your Way to Cash Live

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Check our websitewww.charisamunroe.com
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What’s next…?

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