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Money is never just about dollars and cents. It’s about choices, values, and emotions.

In this Sidebar Advisors episode, Jacquette Timmons — financial behaviorist, speaker, author, and host of the More Than Money podcast — shares how decades of experience have shaped her mission to help professionals, especially attorneys, transform their relationship with money.

Jacquette has seen firsthand that wealth doesn’t erase fear or poor decisions — it only changes the scale.

In this conversation, we explore:

• Why financial well-being starts with understanding the emotions behind money decisions.
• The risk-averse mindset attorneys bring from their work into their personal finances.
• How lifestyle creep, debt, and “herd bias” quietly derail attorneys’ financial health.
• Why financial intimacy—not just transparency—matters for lasting relationships and firm culture.

This episode is a must listen for anyone who still experiences financial stress despite earning well.

Jacquette’s insights remind us: you don’t manage money, you manage your choices around money.

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Erin Andersen, founder of Your Brand Networker, is on a mission to help professionals reclaim joy in their careers. From guiding burned-out attorneys through bold career pivots to introducing a flat-fee hiring model that challenges traditional recruiting, Erin brings fresh thinking to industries where culture and retention matter most.

In this episode, Erin shares:

• How toxic workplace experiences inspired her to build a career around helping others navigate transitions.
• Why attorneys often struggle with identity and financial fears when leaving big law.
• The unique recruiting challenges law firms face — and how her flat-fee approach helps small firms scale strategically.
• The overlooked role of branding and visibility for attorneys, from LinkedIn presence to firm culture.

Whether you’re an attorney rethinking your next step or a law firm leader looking to hire and retain top talent, Erin’s insights will shift how you view careers, culture, and growth.

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Before AI, commercial space exploration, or 3D printing became mainstream, James Wolff was already deep in the weeds - founding startups in college and chasing cutting-edge ideas long before they hit the headlines.

In this episode, James shares how his lifelong passion for technology continues to shape the way he practices law, advises clients, and builds his reputation in the industry.

We explore the winding path that led him from engineering and entrepreneurship to law, and how his side projects —whether speaking on stage, writing books, or serving on forward-thinking boards— help position him as a thought leader in fast-evolving spaces.

This one’s a little geeky, a little strategic, and packed with insight for anyone looking to future-proof their career.