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You know that moment when you realize leading a team feels a lot like parenting? You’re guiding, teaching, and sometimes repeating yourself a hundred times but this time, the “kids” have deadlines and invoices. In this episode of Entrepreneur Encounter, hosts we share an honest conversation about what leadership really looks like behind the scenes. From letting go of control to building trust and boundaries, we unpack the messy, rewarding, and often funny realities of becoming a first-time manager or business owner.

If you’ve ever struggled with delegation, avoided tough conversations, or tried to be everyone’s friend, this episode will feel like a sigh of relief. We get real about the mistakes we made early on, the lessons that shaped us, and how we learned to lead with both empathy and accountability. Whether you’re managing a team, clients, or a growing business, this episode will help you navigate leadership without losing your mind (or your sense of humor).

What to Listen for in This Episode:

From Doer to Leader: Why the biggest shift in management is learning to let go of control and trust the process; even when it’s uncomfortable.

Boundaries Build Better Leaders: How empathy and accountability can coexist, and why setting boundaries isn’t cold—it’s actually an act of respect and love in leadership.

Leadership Lessons (the Hard Way): The story of having to fire someone without guidance and a confession about overpromising to clients reveal the importance of feedback, boundaries, and self-awareness as a manager.

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Want to learn more about how this can work for you and your business, reach out to us!

Connect with Entrepreneur Encounter:

Newsletter: https://tinyurl.com/3azyca95

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

Host Sara Lowell:

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

Website: https://www.youarerembertllc.com/

Host Dana Johnson:

Instagram: https://www.instagram.com/danas.desk.nc/

Website: https://ddvirtualmanagement.com/