Welcome back to Don’t Retire… Graduate! In today’s episode, we’re exploring one of the most critical and overlooked aspects of retirement: transitioning your identity, purpose, and fulfillment as you move into the next chapter of life. Joining me for this conversation is Jack Calhoun, the founder and president of Encore Career Lab. Jack isn’t just a seasoned entrepreneur after leading a wealth management firm from $50 million to over $1.5 billion in assets and selling the business in his early 50s, Jack faced the emotional and identity challenges that often come after a primary career ends. Through his own post-career journey of “wondering and wandering,” Jack discovered firsthand that financial planning alone is never enough.

Jack and I dove into the parallels between our journeys, both as liberal arts majors and as people who built companies, stepped away from the top job, and then wondered “what’s next?” Together, we unwrapped the deeply personal and often daunting process of redefining yourself and finding meaning once the “what do you do?” The question no longer has a simple answer. Jack candidly shared the psychological hurdles many face upon retirement, especially for high achievers who tied their identity so closely to professional success.

We discuss the pitfalls of thinking retirement is only about “doing the math,” and the dangers of the so-called Striver’s Curse where career-driven people lose their sense of purpose and can become rudderless once the striving ends. Jack’s experiences and research led him to develop Encore Career Lab, a program designed to help successful professionals regain their “rudder,” starting with “why,” then the “what,” and finally, the “how.” We explore his three-phase approach to post-career transformation, the importance of generativity (the drive to give back and pass on wisdom), and why building a roadmap for fulfillment, not just finances, is vital in modern retirement.

5 Key Takeaways:

1. Identity Challenges After Retirement: Jack illustrated how even strong, career-driven individuals can underestimate the existential impact of leaving their professional roles, discovering that so much of our identity is tied to what we do and contribute.
2. Purpose Is More Important Than Leisure: We debunked the myth that endless recreation leads to fulfillment, revealing that humans are wired for purpose, meaning, and generativity and that’s what produces happiness beyond financial freedom.
3. Start with Why: Jack’s work with Encore Career Lab emphasizes discovering your “why” before choosing what you’ll do and how you’ll do it post-career; clarity on purpose leads to choices that align with your values and lead to true fulfillment.
4. The Risk of Losing Your Rudder: Without intentional planning, retirees often become overwhelmed, dabble without direction, or feel paralyzed by too many options; a structured process is vital to avoid feeling rudderless or self-conscious about your next steps.
5. Generativity as the Common Thread: As people mature, the drive to give back and share accumulated wisdom becomes a universal impulse. Jack observed that everyone drawn to his program feels a compulsion to help others and leave a legacy making mentorship, teaching, and service recurring encore themes.

Join us for this inspiring conversation on redefining the very nature of retirement from a finish line to a commencement. If you or someone you know is approaching a new phase of life and seeking more than just financial security, this episode will open your eyes to the possibilities of true graduation. Don’t forget to subscribe, rate, and share this episode with anyone eager for a purpose-filled future!

Welcome back to Don’t Retire… Graduate! In this inspiring episode, we’re exploring how to break free from financial overwhelm—especially for those whose brains are wired a little differently. Joining me today is Andrea Ewalefo, founder and CEO of Modern Lady Vibes. Andrea is dedicated to empowering neurodivergent women by helping them harness their unique strengths to build real wealth with her signature 5-step VIBES framework. With her background as a JD, MBA, and former financial advisor, Andrea brings both professional expertise and personal experience to the conversation.

In today’s discussion, Andrea and I dove into the world of neurodivergence—what it means, how it manifests, and why traditional financial advice often doesn’t resonate for people whose executive function operates outside typical norms. Andrea shared her story of being featured in CNBC, her passion for helping women (and men!) who’ve been overlooked by conventional financial education, and the challenges that come with both neurodivergence and societal expectations, especially for women.

We explored Andrea’s VIBES framework, which stands for Vision, Intention, Baseline, Engineer, and Streamline. Andrea explained how automating financial habits, removing unnecessary decision-making, and reducing shame around money management can open doors to financial independence—even if staying “consistent” has always felt impossible. We discussed how different life experiences—gender, late diagnosis, social expectations—impact financial behaviors, and how anyone, regardless of diagnosis, can benefit from a shift away from shame and toward practical, sustainable systems.

5 Key Takeaways:

1. Redefining Neurodivergence in Finance: Neurodivergence includes ADHD, autism, dyslexia, and other ways of thinking outside the “typical” brain. Traditional personal finance guidance usually isn’t built for these experiences—so it’s time for new, more compassionate systems.
2. The VIBES Framework: Andrea’s 5-step approach—Vision, Intention, Baseline, Engineer, Streamline—centers self-acceptance, automation, and upfront decision-making to minimize overwhelm and maximize financial empowerment.
3. Eliminating Shame and Embracing Automation: Regular budgeting advice often causes guilt and decision fatigue. By automating savings, bill payments, and allocations for fun money, you can break negative cycles and focus energy where it matters.
4. Societal & Gender Differences: Women are often diagnosed later with neurodivergence and taught to overcompensate—masking symptoms and fueling perfectionism. Andrea’s approach emphasizes why it’s crucial to address these unique pressures.
5. Community and Support: You don’t have to be diagnosed as neurodivergent—or even a woman—to find value in Modern Lady Vibes. If traditional advice leaves you overwhelmed, Andrea’s inclusive, strengths-focused community and resources might be a game-changer.

Join us as we challenge outdated financial norms and encourage everyone to create a more sustainable—and joyful—path to financial freedom! Don’t forget to subscribe, rate, and share this episode with friends, family, or anyone who’s felt lost trying to fit typical financial advice into their unique life.

Welcome back to Don’t Retire… Graduate! In today's episode, we're diving into a topic that resonates with so many retirees and those preparing for retirement: how to graduate from guilt and finally feel good about spending in retirement. Joining me is Linda Grizely, a personal finance expert and financial wellness speaker who specializes in helping people turn financial overwhelm into empowerment. Linda makes money feel approachable, practical, and human, and today she's here to guide us through the emotional and psychological aspects of financial decision-making, especially as it relates to spending in retirement.

During our conversation, Linda and I explored the shame and taboo that often surround both having and not having money. We discussed the importance of understanding your "money personality," a concept Linda developed to help individuals recognize how they interact with finances and why certain spending or saving behaviors feel easier or more challenging. In real time, I took Linda’s money personality assessment (available free on her website), which revealed me as a "spender"—a money personality that uses finances to invest in memories and express love rather than seeing spending as negative.

Linda shared her ME! Money Method, a strategy that enables individuals (and couples) to set aside guilt-free funds for personal enjoyment, fostering mindfulness over restriction. We unpacked how this method helps different money personalities navigate retirement spending and overcome psychological hurdles, whether fear of running out of money for security seekers or unintentional overspending by risk-takers and spenders. Linda also illustrated, with both professional and personal stories, why self-awareness and reframing our approach to money are crucial for achieving true financial wellness and enjoying retirement.

5 Key Takeaways:

1. Shame Is Universal: Whether you have too little or more than enough, shame around money is common. Recognizing this helps reduce isolation and encourages open, productive conversations about finances.
2. Money Personalities Matter: Linda’s money personality assessment demonstrates that understanding your natural approach to money—whether spender, saver, security seeker, avoider, or risk-taker—can help inform better financial decisions and remove judgment.
3. The ME! Money Method: Setting aside separate guilt-free funds for yourself (and your spouse or partner) empowers you to enjoy life and eliminates the guilt often associated with spending, especially for security seekers struggling in retirement.
4. Self-Awareness Leads to Better Choices: Linda’s work, including her own experience and her husband’s, shows that having a structure around personal spending makes you more mindful and intentional without feeling restricted.
5. Financial Wellness Is Human: True financial wellness is about more than numbers—it’s about understanding psychology, behavior, and emotions, which can free retirees to enjoy their resources without fear or guilt.

Join us as we inspire and educate you on your journey toward financial freedom, empowering you to spend your retirement years with confidence, purpose, and joy. Don’t forget to subscribe, rate, and share this episode with anyone seeking a healthier, happier relationship with their money!