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In this episode, Candace Dellacona, Principal and Shareholder in the Estates & Trusts practice at Offit Kurman, shares how she guides families through the most personal and complex planning issues: from wills and guardianships to elder care, LGBTQ+ planning, and business succession.

We cover:

• Why estate planning is about more than legal documents - it’s about family dynamics, time, and mental health.
• The biggest challenges facing the sandwich generation, from caregiver burnout to family conflict.
• How women disproportionately carry caregiving roles - and what that means for long-term planning.
• Special considerations for LGBTQ+ families, professional athletes, and high-profile clients.
• Practical ways to approach sensitive conversations with parents and loved ones.

Candace’s insights show why estate planning is less about wealth and more about protecting relationships and creating peace of mind.

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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.

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Gail Cummings began her legal career to meet expectations, but the deeper truth was harder to ignore. After more than a decade in Big Law, with a thriving practice and two young children at home, she made the bold decision to pursue her long-standing dream of becoming a psychotherapist.

In this episode, Gail shares her path from lawyer to licensed therapist and executive coach, the emotional and practical hurdles she faced, and why so many attorneys find themselves questioning the career they worked so hard to build.

We also explore the mental health themes that come up repeatedly in her work with attorneys and the growing demand from law firms and bar associations for her expertise.

Whether you're thinking of leaving the law or trying to make peace with staying, Gail offers compassionate, actionable guidance on how attorneys can build happier, more authentic careers.

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In this episode, we sit down with Andrea D’Ambra, Partner and Global Executive Committee Member at Norton Rose Fulbright. Andrea shares her remarkable journey from leaving a major firm to pursue a true partnership track, to navigating Big Law while raising five kids and ultimately rising to leadership at one of the world’s largest law firms.

We talk about her role co-chairing the firm’s Women’s Initiative (WiN), her influential work with The Sedona Conference, where she helps shape best practices for the responsible use of AI in legal settings, and how she balances the intensity of law firm leadership with personal time ( including video games to decompress).

This conversation is honest, inspiring, and packed with insights for attorneys navigating their own careers and values.

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In this episode, Niraj is joined by friend, colleague, and fellow advisor Ian Murray, CFP®, CSLP®.

In this episode they discuss the real-life role student loans play in financial planning - especially for attorneys earning at the higher end of the scale.

They talk through how student loan strategy shifts across compensation tiers, how to balance repayment with long-term planning, and how lifestyle design and financial clarity go hand in hand.

You’ll also hear thoughts on the latest student loan legislation and what income-based repayment means in today’s environment.

Whether you're managing loans, thinking about career shifts, or building a more intentional financial plan—this one's packed with insight.