Finding Purpose25 Helmi 2025

Ep. 45 - Finding Your Voice in Law & Life: Alessandra Cortina's Journey

In this episode of Finding Purpose, I sit down with Alessandra Cortina, founder and CEO of the Cortina Law Group based in Westchester. Alessandra's journey is one of resilience, ambition, and breaking generational expectations. Growing up in a traditional Italian family, she was surrounded by the entrepreneurial spirit from a young age, watching her parents build a restaurant business from the ground up. But while family values and a strong work ethic were ingrained in her, she also faced the challenge of carving out her own path in a world full of strong opinions and expectations.

Alessandra shares how she unexpectedly discovered her passion for law, the struggles of balancing law school, career, and family milestones, and the pressure of being the eldest child in a close-knit Italian household. We explore how she found her voice amidst the noise of tradition, built a thriving legal practice, and learned to navigate the ever-changing landscape of modern business. Whether you're an aspiring entrepreneur, a professional looking for inspiration, or someone struggling to define your own path in life, this conversation is packed with wisdom and insights.

We discuss:
🔥 Growing up in an Italian-American family and how it shaped her values
🔥 How entrepreneurship runs in her blood and the lessons learned from her family's restaurant business
🔥 The decision to become a lawyer and the hurdles of law school and bar exams
🔥 Managing family expectations vs. personal aspirations
🔥 The power of finding your own voice in a world full of opinions
🔥 The evolution of modern business practices and why many traditional mindsets struggle to adapt
🔥 Her journey from human resources at Morgan Stanley to launching her own law firm

🎙️ One of my favorite takeaways from this episode:
Alessandra reminds us that finding our purpose often requires filtering out the noise—especially from those who love us most but may project their own fears onto us. Learning to stand firm in our own decisions, even when met with resistance, is key to creating a life that truly aligns with our values.

Connect with Alessandra Cortina:
🌎 Website: www.thecortinalawgroup.com
📸 Instagram: @thelawyerista

👉 If you loved this episode, please leave a review and share your biggest takeaway!

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