Konversations With Kai

What happens when being the smart one stops working?

On this episode of Konversations with Kai™, Kai talks with Rachael Jencks, confidence coach, entrepreneur, and mom of six, about self-trust, business confidence, and making decisions when there’s no clear right answer.

Rachael shares how being good at figuring things out met the uncertainty of entrepreneurship. She and Kai discuss second-guessing, over-preparing, and waiting for certainty before taking action. Rachael reflects on a difficult business launch, the pressure to prove her business was worthy, and learning to trust herself even when she can’t know how a decision will turn out.

They also talk about balancing business, marriage, and motherhood—and draw a lesson from gymnastics: learning a new skill means being willing to fall while you’re still figuring it out.

About Rachael:

Rachael Jencks is a confidence coach, entrepreneur, and mom of six who knows what it means to juggle big goals, careers, businesses, marriage, family, and a very full calendar. Her work explores confidence, self-trust, and the ways capable, accomplished people can still get in their own way. After years of being good at figuring things out, entrepreneurship challenged Rachael to become comfortable making decisions without certainty—and to trust that whatever happens, she’ll figure it out.

Connect With Rachael

Website: https://www.rachaeljencks.com/

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

TikTok: https://www.tiktok.com/rachaeljenckscoaching/

FREE TRAINING

If I’m So Smart, Why Can’t I Make Money as a Coach?

https://www.rachaeljencks.com/3-step-method-sign-up

What happens to our relationships with other people when we’ve lost our relationship with ourselves?

In this episode of Konversations with Kai™, Kai talks with Anna DiCarlo about losing touch with yourself, adapting to other people’s expectations, and finding your voice again through small, everyday choices. Anna also reflects on grief, faith, accountability, boundaries, and self-forgiveness—and shares how the emotions people experience inform her novel, The Ghost in the Habit.

About Anna
Anna DiCarlo is an author, entrepreneur, and speaker whose work centers on connection to self, self-worth, and becoming emotionally regulated so we can connect more fully with others. After navigating her own struggles with identity, mental health, and finding her voice, a pivotal season in her mid-30s changed the direction of her life. Through her writing, speaking, and work with others, she encourages people to embrace the messy parts of growth and recognize the transformation that can emerge from them.

Connect with Anna
Website: https://www.shoplbn.com/
Facebook: https://www.facebook.com/lbnstorefront
Facebook: https://www.facebook.com/theghostinthehabit
TikTok: https://www.tiktok.com/labellenaturel
The Blueprint: https://www.shoplbn.com/theblueprint