Why I Should Not Have Gone To Law School And How To Avoid A Terrible Mistake (with Jared Correia) | Ep. 4

Law school, big law, lifestyle, AI, legal technology, small firm reality, student loan pressure and legal adjacent careers all collide in this conversation. Host Larry Port sits down with Jared Correia, who walks through his path from small liberal arts college English major and classics minor to Suffolk Law School, small firm practice, bar association work and founder of Red Cave Law Firm Consulting.

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Jared shares that he went to law school with no idea what he wanted to do, discovered he did not like practicing law, and pivoted into consulting after seeing how many firms lacked basic business management. Larry and Jared break down different practice areas, lifestyle practices like estate planning, the grind of personal injury and big law, why so many lawyers are depressed, and how AI and cloud software reshape research, document drafting and staffing. Listeners hear honest advice on knowing why you want to go to law school, understanding debt, exploring legal adjacent work and building skills in communication, sales, customer service and AI.

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👤 Guest Bio

Jared Correia is the Founder and CEO of Red Cave Law Firm Consulting, providing business management consulting services for lawyers and law firms, as well as technology and marketing consulting for legal institutions and legal-facing businesses. A former practicing attorney and bar association administrator, he has worked with thousands of law firms and hosts legal industry podcasts and events. Jared brings honest insight on law school decisions, small firm life, big law, legal technology, AI and alternative paths in the legal world.

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📌 What We Cover

• Going to a small liberal arts college, choosing English and classics without a plan, joining the debate team and deciding to apply to law school late with a middling LSAT.
• How Jared chose Suffolk Law School over Santa Clara, went straight through without a break and then discovered through electives that he did not like any of the traditional profitable paths.
• Why he says he probably should not have gone to law school, and why students should understand what lawyers do, talk to lawyers, shadow, and avoid going in just for money.
• Clear examples of how different practice areas shape real life: personal injury as scratching lottery tickets and eating ramen, estate planning as a lifestyle practice with flexible hours, and the strain of litigation work.
• Honest talk on big law, billable culture, giving away your twenties, and why many lawyers feel trapped with significant student loan payments, old cars, no house and repetitive, stressful work.
• The emotional and mental load of lawyering: worst case scenario thinking, constant client crises, pessimism, and how that bleeds into personal life and fuels depression and burnout.
• Jared’s pivot story: leaving small firm practice, joining a bar association, moving into a consulting role for thousands of lawyers, using cloud software, social media and podcasting to build a profile in legal consulting.
• How AI and legal tech intersect with law firm work, why many lawyers are still not really using AI, what can be automated in document review and drafting, and why future lawyers should build strengths in sales, customer service and prompting AI.

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🔗 Resources Mentioned

• Red Cave Law Firm Consulting
• St....