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It’s Okay to Fail: Leadership, Resilience, and Finding Your Path

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Jackie Winfrey is a former U.S. Navy service member, experienced criminal defense paralegal, and operations director based in North Carolina. She is also an aspiring attorney exploring entrepreneurship and bilingual legal support services.

Here’s a glimpse of what you’ll learn:

  • [02:26] Jackie Winfrey shares her upbringing in North Carolina and the influence of her family’s Mexican restaurant.
  • [02:48] How taking on responsibilities at age 15 helped Jackie develop leadership and business skills.
  • [03:59] Her five years in the U.S. Navy and the experiences that inspired her to pursue criminal defense work.
  • [04:37] What it takes to manage business operations, employee onboarding, budgets, and organizational systems.
  • [05:48] How Jackie combined her paralegal experience, Spanish-language skills, and operations background to pursue entrepreneurship.
  • [07:36] Why speaking Spanish is a valuable professional advantage in the legal industry.
  • [08:54] How bilingual legal professionals help Spanish-speaking clients feel more comfortable navigating legal processes.
  • [11:39] How attending the Hispanic National Bar Association conference inspired Jackie to explore freelance paralegal work.
  • [12:36] The unexpected way a Bad Bunny group chat introduced her to the HNBA community.
  • [13:22] Why taking risks and accepting setbacks are essential parts of personal and professional growth.
  • [14:00] The challenges of navigating higher education as a first-generation Latina and aspiring law student.
  • [16:47] Jackie’s message to the world: “It’s okay to fail.”

In this episode…

Recorded at the Hispanic National Bar Association’s Annual Convention in Washington, D.C., John Gomez and David Arreguin welcome Jackie Winfrey, a former U.S. Navy service member, experienced paralegal, and operations director, for a conversation about leadership, entrepreneurship, resilience, and finding your path in the legal profession.

Jackie shares how growing up in her family’s restaurant in North Carolina taught her responsibility and leadership at an early age. After serving five years in the Navy, she pursued a career in criminal defense before transitioning into business operations and exploring opportunities as an independent paralegal.

The conversation also highlights the value of bilingual professionals in the legal industry, the power of networking through organizations like the HNBA, and the challenges Jackie has faced navigating higher education as a first-generation Latina. Her story offers encouragement to aspiring legal professionals who are still discovering their paths and learning to embrace failure as part of growth.

Quotable moments

  • “Why not start a business? Why not be my own boss?”
  • “It does give people just that comfort of knowing that they’re gonna understand something, a process that’s so scary.”
  • “Coming to this conference has really helped me expand my network and build these relationships.”
  • “You can’t grow if you don’t take a leap and fail a little.”
  • “It’s definitely been a struggle being a first-generation Latina to go to school.”
  • “I found a mentor that helped me lock in a plan.”
  • “It’s okay to fail.”
  • “That’s the only way you grow.”

Action steps

  1. Embrace leadership opportunities early. Take responsibility and develop decision-making skills through real-world experiences.
  2. Use your professional experience to create new opportunities. Identify how your existing skills can help you transition into different industries or launch a business.
  3. Invest in operational efficiency. Build organized systems for managing employees, finances, deadlines, and business processes.
  4. Leverage bilingual skills. Use your ability to communicate in multiple languages to serve clients and communities that need better access to legal services.
  5. Expand your professional network. Attend conferences, connect with mentors, and build relationships beyond your immediate community.
  6. Take calculated risks. Don’t wait for the perfect opportunity before pursuing professional growth or entrepreneurship.
  7. Find mentors who understand your goals. Seek guidance from professionals who can help you navigate educational and career decisions.
  8. Develop strong interpersonal skills. Communication, leadership, and the ability to connect with others are essential to success in the legal profession.
  9. Accept failure as part of growth. Learn from setbacks and continue moving toward your long-term goals.

Sponsor for this episode…

This episode is brought to you by Gomez Trial Attorneys, a personal injury law firm based in San Diego.

Award-winning attorney John Gomez developed a nationally recognized legal team that goes above and beyond for injured clients.

With numerous designations, distinctions, and top-notch resources, we have what it takes to fight and win against major corporations.

For a free case evaluation, visit https://www.thegomezfirm.com/contact/.