What does it cost to lead at the highest level? Jess Bass Bolander (SVP at Lockton) joins Dr. Alison to discuss the "unhealed eight-year-old," the weight of leadership, and why staying at the table is the only way to impact change.

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In Season 2, Episode 3 of (un)conversations, we explore the mental load of high-stakes leadership. Jess shares her journey from a "scrappy" start in the insurance industry—pivoting from a path in law—to becoming a Senior Vice President. She reveals how childhood survival triggers show up in the C-suite and why emotional intelligence is a leader's most critical tool.

Topics Explored

• The (UN)word Effect: Exploring (UN)breakable, (UN)relenting, and (UN)afraid.

• Executive Leadership: Managing high-stakes responsibility and burnout.

• Women in the Workforce: Why we must stay in the game to move the needle.

• Mentorship & Advocacy: The power of having a champion in the room.

🎯 What You’ll Learn:

• Why "If you're not at the table, you're on the menu."

• Navigating childhood survival triggers (The Unhealed 8-Year-Old) in the office.

• The transition from Law to Business: Lessons from a major career pivot.

• How to manage the mental load of executive decision-making.

• Real-world lessons on building trust-based cultures at Lockton.

Timestamps00:00:00 The Reality of Executive Pressure: Why Leadership Has Weight 00:00:02 Episode Teaser: Childhood memories and financial independence. 00:01:06 Introduction & Welcome: Jessica Bass Bolander, SVP of Lockton. 00:01:52 The (UN)word Effect: Reflecting on the leadership journey. 00:04:49 (UN)word #1: (UN)breakable – Overcoming childhood turbulence. 00:07:53 The Pivotal Moment at Age 13: A commitment to self-reliance. 00:09:10 Early Career Hustle: From waitress to SVP. 00:09:27 Leadership Philosophy: Treating everyone like a star. 00:12:01 (UN)word #2: (UN)relenting – Persistence in adversity. 00:15:18 Pivoting from Law to Business: The "scrappy" start in insurance. 00:29:43 (UN)word #3: (UN)afraid – Motherhood and career risk. 00:30:46 Balancing Executive Roles and Motherhood. 00:33:15 Building Culture at Lockton & with clients. 00:39:09 Mental Health in the Workplace: Breaking the taboo. 00:44:50 The "Unhealed Eight-Year-Old" in the Workplace. 00:46:30 Advocating for Women in the Workforce. 00:55:34 Ask Dr. Alison: Guest Q&A. 00:58:45 Final Thoughts: Defining your own success. 01:00:56 Closing Remarks & DFW Community Impact.

🔗 Connect with Dr. Alison Schmidt

Website: www.unconventionllc.com

LinkedIn: https://www.linkedin.com/in/alison-l-schmidt-phd-bcc/

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

🔗 Connect with Jess Bass Bolander

LinkedIn: https://www.linkedin.com/in/jess-bass-bolander-63213114/

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

A special thank you to DJ Doug Jackson for composing and producing the official (un)conversations theme song: https://soundcloud.com/dougjackson

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