Meet Lisa Chastain

We recently connected with Lisa Chastain and have shared our conversation below.

Lisa, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?
I gained self-confidence and self-esteem through life’s lessons. Much like my father, who navigated the “school of hard knocks” after barely graduating high school, I inherited a resilient spirit. I embody the “all in” mentality – a trait that has been with me since childhood.

Recalling the early years, I vividly remember the persistent pursuit of mastering bike riding. Each fall, bruise, and setback became a stepping stone to success. This tenacity defines my character, shaping my confidence and self-esteem.

Raised without a chorus of voices encouraging me to chase my dreams, I forged my path through determination and hard work. As a student athlete, I wasn’t born with innate talent; instead, my confidence emerged from learning how to endure falls, blisters, bruises, and losses, always rising to continue the journey.

This resilience extends beyond sports into the realms of business, love, and leadership. Whether serving as the high school student body president or navigating a challenging divorce in 2017, I’ve earned my confidence by facing adversity head-on, armed with the knowledge that a robust support system and unwavering determination can conquer any obstacle.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
For over two decades, my mission has been to empower women in their lives. With a diverse background as an academic advisor, financial advisor for high-net-worth individuals, and now a money coach, my qualifications extend beyond work experience. Having faced the brink of financial collapse myself, I’ve spent the past decade learning the realities of achieving dreams – a journey far removed from the glamorous portrayals on Instagram. Armed with industry knowledge and personal experiences, I guide clients in reshaping their mindset around money, employing a strategic financial framework centered on healthy spending rather than restrictive budgeting, enabling them to build wealth while enjoying life.

My transformation began when financial adversity forced me, even as a financial advisor, to make crucial mindset and financial changes. A blue-collared girl, I sought simple financial goals, like savings and secure retirement, mirroring the aspirations of many successful women I now work with. Leaving my role as a financial advisor in 2016, I embraced my true calling as a Personal Finance Coach. Despite real financial struggles, from the peak of my career in 2011 to investing $100,000 to start my own business, I reinvented myself through failures and divorce. The simple strategies and tools I acquired during this journey were instrumental in getting my financial life on track.

Today, you can find me featured in major publications and media outlets, including CNBC, NBC News, MSN Money, O – The Oprah Magazine, Fortune, and Entrepreneur Magazine. As a best-selling author, the host of the Real Money podcast, and the creator of the Stop Budgeting System, I share my insights to support individuals in creating the life they desire, free from the isolation of financial stress and rigid budget constraints. My journey has taught me how to live a fulfilling life, and I’m here to help others do the same.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

At the core of how I lead is this trio of qualities: tenacity, resilience, and a knack for having those real talk sessions with myself. Tenacity is like my secret weapon, pushing me to tackle challenges head-on and keep going even when things get tough. It’s that stubborn commitment to hitting my goals, whether they’re personal or professional.

Resilience is another big player in my leadership style. I’ve learned that setbacks aren’t roadblocks; they’re chances to grow. Every stumble turns into a lesson, making me bounce back even stronger. It’s a must-have quality that helps me navigate the twists and turns of leadership.

Then there’s the part where I roll up my sleeves and get into some serious self-reflection. Leadership isn’t just about telling others what to do; it’s about looking in the mirror and working on myself. By facing my own weaknesses and pushing for continuous personal growth, I’m creating an environment where improvement is the name of the game. These honest chats with myself? They’re like my secret sauce for evolving as a leader.

In a nutshell, my leadership journey is this mix of tenacity, resilience, and the guts to dig deep into self-reflection. These qualities don’t just affect how I tackle challenges; they also shape the vibe of the team, creating a space where perseverance, adaptability, and always getting better are the norms.

Set Clear Goals: Stay focused on short term goals to give yourself something to strive for.

Keep Positive States: Cultivate a positive mindset to help you stay motivated during tough times.

Embrace Challenges: Instead of avoiding difficulties, see them as opportunities for growth and learning.

Learn from Setbacks: Analyze your failures to extract lessons and insights that can help you improve.

Develop Coping Mechanisms: Identify healthy ways to cope with stress, whether through exercise, mindfulness, or supportive networks.

Reflect: Dedicate time to reflect on your actions, decisions, and experiences.

Seek Feedback: Actively seek feedback from others to gain different perspectives on your strengths and areas for improvement.

Embrace Vulnerability: Be open to acknowledging your weaknesses and areas where you can grow. Vulnerability is a strength.

Stay Informed: Keep yourself updated on industry trends, best practices, and new insights relevant to your field.

Connect with Peers: Build a network of like-minded individuals who share similar goals and values.

Seek Mentors: Find mentors who can provide guidance based on their experiences and help you navigate challenges.

Share Experiences: Engage in open discussions with others to share and learn from different leadership journeys.

Remember, improvement is a gradual process, and consistency is key. Embrace challenges, learn from setbacks, and celebrate your successes along the way. Each step you take toward enhancing these qualities contributes to your personal and professional growth.

Alright so to wrap up, who deserves credit for helping you overcome challenges or build some of the essential skills you’ve needed?

In my journey of self-discovery, my coaches and mentors have played an invaluable role. I attribute much of my growth to the ongoing investment in myself, consistently seeking guidance from top-notch mentors and coaches. This deliberate choice allows me to reach beyond my current capabilities, gaining real feedback, support, and valuable shortcuts from experts who possess insights I might overlook.

The decision to hire individuals to shed light on my blind spots has proven to be the cornerstone of my continuous growth in various aspects of life. By embracing this proactive approach, I not only receive the guidance needed to navigate challenges but also uncover hidden potential within myself. It’s a journey of constant elevation, propelled by the wisdom and perspective of those who can see beyond my immediate vision.

In essence, surrounding myself with mentors and coaches has become the catalyst for ongoing self-improvement. It’s a testament to the power of seeking external perspectives, an investment that pays dividends in my personal and professional evolution. Through this collaborative effort, I’ve come to appreciate the profound impact of leveraging the expertise of others on the path to becoming the best version of myself.

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Image Credits
Photos by: Casey Jade Photography

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