How gaining financial safety gives you the freedom to dream episode artwork

EPISODE · Aug 29, 2025 · 42 MIN

How gaining financial safety gives you the freedom to dream

from WILL - Women Interested in Leaving Law · host WILL - Women Interested in Leaving Law

Imagine feeling stuck in a high-paying legal job as you’re buried deep in student loan debt. Imagine having everything you ever wanted in a career - Your dream job right in front of you, and then realizing you absolutely hate it. Imagine feeling unsure how to make a change…until one conversation shifts everything. In this inspiring episode, Jessica Medina shares how she went from being completely burnt out and in financial overwhelm, to a place of freedom, clarity, and renewed energy. She talks through the dawning realization that her dream job in enforcement is far from what she imagined. Burnt out, indebted and lacking love in her career, Jessica chose a new career path that not only helped her decrease her own debt, but help others in the same way. In this episode, she talks about: How the fear of financial security shuts down processing and the ability to think. Opening the mindset of clients to see beyond the ‘safe path’ and begin to feel passionate and dream. How she helps clients gain the freedom to make intentional choices. Many lawyers feel stuck in their jobs because of financial obligations, especially student loan debt. But once they gain clarity and control over their finances, it opens up real options: career pivots, sabbaticals, travel, or simply breathing room to reassess.  If this sounds like you, then we invite you to listen in and begin to dream again.   About Jessica Jessica Medina is a lawyer turned Accredited Financial Counselor on a mission to help attorneys create the financial freedom they need to do big things. She graduated from Columbia Law School in 2004 as a single mom of twins with over $200,000 in student loans and went straight to work at a big law firm.    After eight years she switched roles and became Senior Counsel at the Division of Enforcement at the United States Securities and Exchange Commission. She left the government to work in an area of the financial industry outside of the securities world and now teaches other lawyers how to use their money to finance their dream lives. She especially enjoys working with her WILL member-clients to help them craft their exit plans and pursue their true passions. Learn more about Jessica Medina: www.jessicamedinallc.com. Connect with Jessica on LinkedIn and Instagram @jessicamedinallc. The WILL Podcast is hosted by Elena Deutsch, a dedicated legal career coach and catalyst. This podcast is more than a good listen. It may inspire you. As WILL Alumni and Guests break the confines of traditional practice, you’ll see that change is not just possible for them, but for you too.  Feel stuck, unhappy and ready to explore a WILL journey of your own? Book your consultation with Elena: https://womeninterestedinleavinglaw.com/book-a-call   Follow LinkedIn: https://www.linkedin.com/in/elena-deutsch/  Instagram: www.instagram.com/womeninterestedinleavinglaw  Facebook: https://www.facebook.com/womeninterestedinleavinglaw Web: https://womeninterestedinleavinglaw.com 

Episode metadata supplied by the publisher feed · Published Aug 29, 2025

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How gaining financial safety gives you the freedom to dream

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