Wealth is often portrayed as polished and effortless from the outside, but the truth behind it is far less glamorous. We are often told that happiness follows achievement: the house, the lifestyle, the recognition. Yet many of us reach those milestones only to find they don’t bring the fulfillment we expected. As I discussed with my recent guest, luxury real estate expert Jane Bond, real growth begins when we strip away appearances and start asking what truly matters.
In our conversation on the Real Money podcast, Jane and I explored what it means to take back our agency, rebuild with intention, and redefine success on our own terms. Her journey of navigating a demanding career while finding authenticity in a competitive space is a powerful lesson. It’s about aligning your work with who you are not who you think you should be. This episode offers a roadmap for anyone ready to build a life and career rooted in truth, resilience, and genuine joy.
Unpacking the Illusion of Success
Reconstructing From an Authentic Foundation
Jane explained that rebuilding her life and career started with truth. When everything around her felt overwhelming; business, environment, and expectations, she chose to pause and seek clarity over chaos. By identifying what genuinely mattered, she built outward from a stronger foundation.
Her process involved three key steps:
- Step back to reflect instead of react. This creates space to understand your motivations and desires without external pressures.
- Identify what aligns with your long-term values. True success is rooted in choices that serve both your stability and your purpose.
- Re-engage with intention. Return to your goals only when your choices feel right and serve your authentic self.
Through this recalibration, Jane found strength not in appearances but in self-awareness. The groundwork for lasting happiness comes from deliberate truth, not the illusion of success.
Overcoming Challenges in a High-Stakes World
Jane operates in the high-pressure, high-visibility world of luxury real estate. She learned that breaking into and thriving in this market takes full commitment. Her success came when she stopped chasing the appearance of achievement and focused on consistent, intentional work. Instead of using social media for vanity, she began sharing genuine stories and insights, allowing her audience to connect with her, not just her listings.
There came a point when she had to step away from old habits to reassess her direction. Walking away from a business or a comfortable lifestyle isn’t failure; it’s recalibration. That decision gave her the space to find clarity and energy again. Jane reminded us that not making a decision is still a decision. By choosing to pause, she stopped stress from controlling her work and returned stronger and more focused.
This shift also meant focusing on the process, not just the outcome. Chasing milestones like titles and sales numbers left her feeling drained. She realized that progress happens when you commit to the daily process; the calls, the learning, and the relationship-building. When you trust the process, the results will follow.
Empowering Women in Wealth and Real Estate
Jane and I are both passionate about empowering women to build wealth with confidence and purpose. Success without fulfillment feels empty. Confidence is not something you’re given; it’s something you build by doing; taking risks, learning from failures, and standing firm in your choices.
We stay committed to learning the systems that sustain wealth. Real estate, finance, and marketing all demand that we stay intentional and data-driven. Instead of multitasking without direction, we choose tools that support structured growth: budgets, CRMs, investment trackers, and consistent education.
Key Actions:
- Use social media with purpose, sharing expertise instead of superficial updates.
- Surround ourselves with mentors and skilled partners who strengthen our strategy.
- Treat financial literacy as an ongoing investment, not a one-time achievement.
Building Generational Stability and Influence
Wealth is about more than just money; it shapes families and communities. Every decision you make about investments, savings, and business ownership creates a model for others. Jane emphasized that building a legacy means teaching those who follow how to manage money, make informed choices, and pursue independence. For women looking to invest in real estate, Jane’s advice is clear: get educated. Understand the language of the industry and the various financial vehicles available. Real estate is a powerful tool for creating generational wealth, but you must know how to use it effectively. Find an educated professional who can help you navigate the process and build a strategy that works for your unique situation.
The Mindset of the Wealthy
Wealthy people understand that money is energy. It flows toward clarity, confidence, and purpose. They don’t chase it; they attract it. Jane explained that her most successful clients see money as a tool, not a measure of self-worth. They invest in assets, in mindset, and in relationships.
This approach requires a healthy relationship with money. When you detach your self-worth from possessions and connect your work to a deeper meaning, you make choices that feel right rather than just look right. Money becomes a resource that serves your goals, not a ruler that dictates your life. By treating it that way, you can plan and act from a position of strength instead of anxiety.
Identifying Niches and Building Investment Paths
Wealth grows when we understand where our strengths fit best. In real estate and other ventures, staying focused on a chosen segment allows us to sharpen our skills and create systems that scale. We look for areas where our insight solves problems or adds value others overlook.
Key steps we follow:
- Study the market and find gaps.
- Surround ourselves with people more skilled or organized than we are.
- Adjust strategies but remain committed to the long-term plan.
By refining our niche and trusting the process, we build sustainable success instead of temporary wins.
The Power of Your Support System
Jane’s journey highlights a universal truth: no amount of career success can replace the grounding that comes from close family and community ties. When she felt burnt out, her family reminded her who she was outside of her titles. They saw through the image and helped her reset when she started chasing validation instead of fulfilment.
Surround yourself with people who challenge you, not just cheer you on. Trust grows when you drop the need to appear perfect and allow others to help. This takes humility, but it allows you to focus on what truly matters. Releasing the habit of comparison is equally important. When you stop measuring your progress by outside standards, you find the freedom to define what happiness and success look like for you.
Your Path to Authentic Success
Jane Bond’s story is living proof that women can redefine success and own their future. It isn’t about having it all figured out. It’s about having the courage to be fearless, take risks, and follow your heart. Wealth isn’t just about what you have; it’s about what you believe you can create and who you are becoming. The greatest abundance is an abundance of joy.
ABOUT LISA CHASTAIN:
Lisa uses many tools that she used throughout her money journey and invites you to try them as well. As a first step, she recommends reading her book, Girl, Get Your $hit Together in which she helps women tackle their financial story and shares her entire story. After reading the book, she invites listeners to join the Stop Budgeting System– the very method she used to gain financial freedom and clarity.
ABOUT MY NEW BOOK:
I’m beyond excited to share that Stop Budgeting Start Living is officially here! This book is the culmination of years of working with women who are ready to rewrite their money stories and step into financial confidence.
Inside, you’ll find strategies to uncover the roots of your money mindset, break free from limiting financial patterns, and create a new path toward wealth and independence.
This release feels especially powerful as we honor the progress women have made financially—and the bold steps we’re still taking together. I can’t wait for you to dive in, apply these tools, and start building the financial future you deserve.
Your journey to living fully, without the weight of restrictive budgeting, starts now.