On the Law Practice podcast, host Terrell interviews career coach and former attorney Dena Lefkowitz about navigating a legal career without burning out. Dena shares how, after over 20 years practicing law, she realized law school didn’t prepare lawyers for the business of law—networking, marketing, and sales—and that lawyers themselves must generate business. She describes feeling embarrassed after discovering that litigation was a poor fit for her personality and values, and warns against “doubling down” on past decisions when a role harms your health or life. Dena explains using values and the five-factor personality traits (openness, conscientiousness, extroversion/introversion, agreeableness, neuroticism) to evaluate fit, and discusses finding outlets or pivots when misaligned. She recounts a back injury that prompted a change to in-house counsel work aligned with her values, and highlights her book, "Winning in Your Own Court."

00:00 Lawyers Are Miserable
00:12 Podcast Intro Disclaimer
00:50 Meet Dena Lefkowitz
01:33 Two Things Law School Missed
02:23 Wrong Practice Area Realization
04:20 Embarrassment And Sunk Costs
06:17 Trapped By Lifestyle Choices
07:50 Values Driven Career Pivot
08:50 Big Five Personality Factors
10:32 Misalignment And Mental Health
13:00 Injury Forced A Change
14:24 Book Title And Key Laws
15:44 How To Contact Dena
16:15 Final Thanks And Outro