Upticks: What Your Wealth Might Say About You
By Luke Sullivan on June 27, 2025
What can you learn from your wealth? Jake and Cory reveal how your financial decisions reflect your values, fears, and ambitions—and ways to help make sure your money is aligned with what matters most. Learn ways to identify blind spots, avoid emotional spending, and use a simple framework to help bring clarity to your financial life. Real stories, practical strategies, and a mindset shift to help you build a more intentional future.
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Read an overview of the conversation below
The Emotional Echo of Wealth
Wealth is often seen as a neutral measure of success, but as Jake and Cory explore in their conversation, it can also act as a mirror reflecting our deepest values, fears, and ambitions. Cory poses a powerful hypothetical: “I [money] was supposed to make you feel safe, why are you still afraid?” This question encapsulates the emotional complexity that often accompanies financial success. Many individuals accumulate wealth with the expectation that it will bring peace, only to find that the underlying anxieties can remain unresolved.
Jake adds that wealth can magnify both the best and worst in us. “Maybe you drink too much… or maybe you’ve got 20 purses,” he says, not to judge but to illustrate how unchecked spending can reflect deeper emotional needs. The key takeaway is that money doesn’t inherently provide peace or comfort—it merely amplifies what’s already present. Without introspection, wealth can become a tool for avoidance rather than empowerment.
Aligning Money with Meaning
A central theme of the discussion is the importance of aligning financial decisions with personal values. Jake shares his own approach: “I don’t spend money on things that aren’t aligned with my values… I’m not a casual shopper. When I buy things, it’s very intentional.” He even notes that he’s never bought anything on Amazon, emphasizing his commitment to mindful consumption.
Cory acknowledges that this alignment is easier said than done. “It can sound touchy-feely,” he admits, “but the reality is it’s a challenge.” The process begins with self-reflection—understanding what truly matters to you and then building a financial plan that supports those priorities. Jake encourages listeners to “get real with yourself” and identify what’s important before allocating dollars. This clarity transforms money from a source of stress into a tool for living a purpose-driven life.
Wealth as Identity and Influence
Cory notes that people may unconsciously use money to protect a self-image: “You’re the provider, or you’re the success story, or you’re not allowed to lose.” These internal narratives can drive financial decisions that are more about preserving ego than achieving meaningful goals.
Jake highlights the concept of “status signaling,” contrasting old money’s understated elegance with new money’s flashy displays. “I buy really high-quality suits and ties, but most people wouldn’t know what brand they are,” he says. This distinction underscores the idea that how we use money can either reflect authenticity or serve as a mask. The conversation also touches on legacy anxiety—how much to leave to children and whether to disclose wealth to them—revealing yet another layer of how money intersects with identity and family dynamics.
The Framework: Origin, Meaning, Impact
To help listeners evaluate their relationship with wealth, Jake introduces a simple framework: origin, meaning, and impact. This structure encourages deeper reflection and helps individuals move beyond viewing money as just a number.
- Origin – Where did your wealth come from? Was it earned through years of work, inherited, or built through entrepreneurship? Understanding the source of your money helps you appreciate its context and emotional weight.
- Meaning – What does your wealth represent to you? Is it freedom, security, status, or legacy? This step is about identifying the emotional and psychological significance you attach to your finances.
- Impact – How does your wealth influence your behavior and decisions? Does it make you more generous, more cautious, or more confident? This is where you assess how your financial resources shape your daily life and long-term goals.
Jake and Cory both share personal reflections using this framework, showing how it can help bring clarity and purpose to financial planning.
From Pressure to Purpose
The final segment of the podcast emphasizes the transformative power of clarity. Cory observes that many retirees feel lost after leaving the workforce because their identity was tied to their career and financial goals. “They envisioned this period of time would be something very specific, and then when they get there… they don’t feel like they’re in the right place.” This disorientation underscores the need for a purpose that transcends financial accumulation.
Jake and Cory advocate for a values-based approach to financial planning. Jake shares his personal purpose: “Inspiring others to live happy and healthy lives.” He explains how this North Star guides all his decisions, making it easier to spend or save with more confidence. “Money is emotional,” he concludes. “We want to use wealth to create clarity, not confusion.” Cory adds, “You’re not going to outgrow fear by getting richer. You’re going to outgrow it by getting clearer.” Ultimately, Jake and Cory encourage you to see wealth not just as a measure of success, but as a mirror reflecting who you are—and who you aspire to become.
Wealth isn’t just a number—it’s a reflection of your values and choices. When you understand where your money comes from, what it means to you, and how it shapes your life, you can use it with purpose. Take a moment to reflect: what is your wealth saying about you?
Thank you for tuning in, we hope you have a great week!
