Women's Money Wisdom

Money isn’t just math. It’s emotion, identity, and sometimes a whole lot of anxiety, even for people who are objectively doing “fine” financially. Melissa Joy, CFP® sits down with speaker, author, and coach Josie Ann Lee to unpack why so many people feel uncomfortable talking about money, and how to move from financial anxiety to real confidence.

They explore why anxiety is a normal stage of learning, how financial jargon and “expert speak” can unintentionally shut people down, and what it looks like to create a more human-centered experience in financial conversations.

Josie shares her practical “Service Wrapper” framework - four simple tools that help people feel safer, more in control, and better equipped to engage in money decisions without shame. Melissa connects those ideas to what actually happens in financial planning meetings, especially for women navigating a system that wasn’t historically built with them in mind.

What You’ll Learn

• Why money discomfort is common even when you’re doing a decent job financially
• How taboo, culture, and history (especially for women) shape financial confidence
• The Four Stages of Learning and why the “anxiety zone” is normal
• How jargon creates a communication gap — and what advisors can do differently
• Josie’s “Service Wrapper” framework: Yes And, Sincere Gratitude, Clarifying Questions, and Giving Choices
• How clarifying questions reduce shame and improve understanding on both sides
• Why autonomy matters — and how choice builds confidence in financial decisions
• The difference between transactional advice and relationship-based planning (and why it affects outcomes)
• How to interview and choose a financial professional based on values and fit
• Where to find Josie’s book and learn more about her work

Connect with Josie: www.josieannlee.com
Book: The Superpower of Service (available on Amazon)

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Medicare is a cornerstone of most retirement plans, but it’s also a brand-new system for people who’ve spent decades on employer coverage. Melissa Joy, CFP® sits down with Cameron Giardini of to break down what Medicare is, when you actually need to enroll, and how to avoid the most common (and costly) mistakes.

They cover the major coverage paths (Original Medicare + Medicare Advantage vs Medigap), why your first enrollment decision at 65 can affect your options later, and what higher earners need to know about IRMAA surcharges. Cameron also explains a key HSA pitfall, shares what’s changing heading into 2026, and points listeners to free education resources to start learning without overwhelm.

What You’ll Learn

• What Medicare is (and isn’t), and when it typically starts
• When to begin planning, and how to check eligibility and costs
• When you can delay Medicare past 65 without penalties
• The key decision: Medicare Advantage vs Medigap (and what each really means)
• Why your first Part B enrollment window matters for lifetime flexibility
• What IRMAA is, how it’s calculated, and how to appeal it after retirement
• How HSAs interact with Medicare and what not to do at 65
• What’s getting more expensive in 2026 and why “choice” may continue shrinking
• How adult children can help parents by first identifying what coverage they actually have

Connect with Cameron: https://gmedicareteam.com/

Youtube: www.youtube.com/@GiardiniMedicare

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Financial confidence doesn’t come from knowing everything. It comes from knowing what questions to ask.

In this episode, Melissa Joy, CFP®, is joined by Tony Steuer, a longtime personal finance educator, insurance analyst, and host of the Get Ready Before Life Happens podcast.

Tony shares how his early career as an insurance agent led him to a deeper mission: helping people understand why smart, capable individuals often end up with financial products that don’t truly serve them. Over decades of consulting with financial planners, attorneys, and trust officers, Tony saw firsthand how complexity, commissions, and behavioral blind spots can quietly derail good financial decisions.

Together, Melissa and Tony unpack how behavioral finance shows up in real life, especially around insurance and risk management. They discuss why permanent insurance products are often misunderstood, how surrender charges and commissions impact long-term outcomes, and why many people feel emotionally stuck in policies that no longer fit their lives.

The episode wraps with an important discussion on financial scams and red flags, including pressure tactics, secrecy, and “too good to be true” promises, and why these warning signs matter not just for ourselves, but for aging parents and the next generation.

Key Takeaways

• Why financial fluency starts with asking better questions, not memorizing answers
• How behavioral finance influences insurance and investment decisions
• When permanent life insurance can make sense and when it usually doesn’t
• What surrender charges really mean and why they matter
• Common red flags of financial scams and bad actors
• How values, communication, and education shape long-term financial confidence

To learn more about Tony’s work, tools, and resources, visit tonysteuer.com and listen to Get Ready Before Life Happens wherever you get your podcasts.

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What happens when a world-changing technology attracts trillions of dollars in investment and how do you avoid being on the wrong side of the boom?

On this episode of the Women's Money Wisdom podcast, Melissa Joy is joined by Kai Wu, founder and chief investment officer of Sparkline Capital, for a thoughtful, data-driven conversation about AI and its real investment implications.

Rather than focusing on hype or fear, this discussion centers on capital allocation, specifically what happens when massive amounts of money pour into infrastructure. Using historical parallels like the railroads and the dot-com telecom buildout, Melissa and Kai explore why transformative technologies don’t always translate into transformative returns for the companies building the underlying systems.

You’ll hear what “CapEx” actually means, why AI requires unprecedented spending on chips and data centers, and how today’s market concentration around the largest tech companies creates both opportunity and risk. 

This episode is especially helpful if you’ve benefited from recent market gains but are wondering about concentration risk, diversification, or how to think more strategically about AI exposure in your portfolio.

In this conversation, you’ll learn:

• Why a transformative technology does not automatically mean a great investment
• What capital expenditures (CapEx) are and why AI infrastructure is so expensive
• How past technology booms rewarded users more than infrastructure builders
• Why highly capital-intensive companies often underperform over time
• How S&P 500 concentration may create hidden portfolio risk
• What “AI early adopters” are and why they may offer overlooked opportunity
• How to think about diversification without abandoning innovation

Whether you’re managing significant wealth or simply trying to make smarter long-term decisions, this episode offers practical insight to help you think clearly — without hype, panic, or binary thinking.

Follow Kai and read his research: https://sparklinecapital.com

X: https://x.com/ckaiwu

LinkedIn: https://www.linkedin.com/in/ckaiwu/

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

On this episode of the Women's Money Wisdom podcast, Melissa Joy is joined by Michelle Taylor, founder of Women in Wealth, for a practical, honest conversation about what actually creates long-term financial stability for women.

Rather than focusing on fear or restriction, this discussion centers on habits — the everyday behaviors that help women build confidence, resilience, and freedom with money over time. Together, Melissa and Michelle break down the six core habits they see consistently among women who feel financially secure and in control, regardless of income level.

You’ll hear why tracking your money builds confidence (not stress), how “paying yourself first” creates momentum, and why investing — even in small amounts — is non-negotiable. The conversation also reframes budgeting as a flexible spending plan, explores how to set financial goals that actually align with your values, and explains why regular “money dates” can transform how you relate to your finances.

This episode is especially helpful if you’ve ever felt successful in life but uncertain about money, struggled with confidence around financial decisions, or wanted a healthier, more empowering approach to building wealth.

In this conversation, you’ll learn:

• Why awareness is the foundation of financial confidence
• How paying yourself first prevents burnout and financial guilt
• The difference between restrictive budgets and flexible spending plans
• Why investing early matters more than investing perfectly
• How to set financial goals that reflect your version of success
• Simple ways to build accountability through regular money check-ins

Whether you’re just getting started or refining your financial habits, this episode offers practical guidance you can use immediately — without shame, overwhelm, or unrealistic expectations.

Follow Michelle: https://www.instagram.com/women_in_wealth/

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What happens when you do everything “right” and still feel unfulfilled?

Melissa Joy, CFP®, sits down with Regina Sih-Meynier, PharmD, a former clinical and pharmaceutical industry leader who followed a quiet inner nudge toward a completely different kind of success. Regina shares how growing up in an immigrant family shaped her drive for security and achievement, why the traditional “success checklist” did not deliver the fulfillment she expected, and what ultimately helped her pivot into entrepreneurship, intuitive work, and a more flexible life.

They talk about the midlife moments that can throw everything off course, from career disruption to caregiving responsibilities, and why financial planning can be a stabilizing force during big transitions. Regina also explains what she means by “whispers” from within, how intuition can show up through the body, and why having a practical runway and support system can make all the difference when you are building your next chapter.

What you’ll learn

• Why hitting major milestones can still leave you feeling disconnected
• How Gen X and older millennial women were conditioned to overachieve and overdeliver
• What it looks like to pivot without burning down your entire life overnight
• How intuition can show up as body intelligence and internal guidance
• Why financial stability can create the space needed to hear what you actually want
• The mindset shift from “income only comes from a paycheck” to multiple streams and possibilities
• How to approach midlife change with flexibility, resilience, and intentional tradeoffs

Author of "A Thousand Whispers from Within"

Coming Feb 2026, Manuscripts Press - available Feb 16th on Amazon.

📧 [email protected]

🌐 www.reginasihmeynier.com

📸 IG: @reginasihmeynier

💼 LinkedIn: Regina Sih-Meynier, PharmD

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Employer retirement plans can be one of the most powerful wealth-building tools available, yet they are also among the most confusing. In this episode of the Women's Money Wisdom podcast, Melissa Joy, CFP®, breaks down how to make the most of your workplace retirement benefits in 2026.

Melissa walks through the key retirement plans many employees have access to, including 401(k), 403(b), and 457 plans, and explains why 2026 is a pivotal year for retirement planning. With multiple legislative changes now in effect, including SECURE Act 1 and 2 and new tax rules impacting catch-up contributions, understanding your options has never been more important, especially for high earners.

This episode covers updated contribution limits, new catch-up contribution rules for those over age 50, and the temporary super catch-up opportunity for individuals ages 60 to 63. Melissa also explains the new Roth mandate for high earners, what it means for your tax strategy, and how it may change the way you approach retirement savings going forward.

Beyond contribution limits, Melissa explores advanced planning opportunities such as after-tax contributions, mega backdoor Roth strategies, and how different employer plan designs can dramatically affect how much you are able to save. She also highlights commonly overlooked strategies for dual-income households, spousal IRAs, and the growing role of Health Savings Accounts as an extension of retirement planning.

If retirement planning feels overwhelming, this episode offers clarity, structure, and actionable guidance to help you confidently use your employer benefits to support your long-term goals.

Key topics discussed include:

• 2026 retirement contribution limits and what’s changed
• Catch-up and super catch-up contribution rules
• The new Roth requirement for high earners over age 50
• Coordinating retirement savings for couples
• Using HSAs as a long-term retirement strategy
• Mega backdoor Roth opportunities and plan design considerations
• Common mistakes that can reduce employer matching

For personalized guidance, Melissa encourages listeners to review their options with a financial planner to ensure their retirement strategy aligns with both current tax laws and long-term goals.

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Long-term care is one of the most personal topics in financial planning, and also one of the most frequently avoided.

Melissa Joy, CFP®, is joined by Pearl Planning colleague Alexa Kane, CFP®, to unpack how families can think about care earlier and more realistically.

This conversation goes beyond nursing homes to explore in-home care, assisted living, and memory care, along with the emotional and financial realities families face when care is needed. Melissa and Alexa explain why long-term care planning often affects women more heavily, why waiting until later in life can limit options, and how today’s long-term care solutions differ from the policies many people remember from past generations.

Rather than assuming insurance is the answer for everyone, they walk through how Pearl Planning approaches long-term care thoughtfully, weighing costs, health considerations, family dynamics, and alternatives. The discussion also highlights what modern hybrid policies are designed to do, how underwriting works, and what options exist for those who cannot or choose not to pursue insurance.

Key takeaways include:

• Why long-term care planning is often a bigger issue for women
• How rising care costs can impact retirement plans and family decisions
• The importance of starting the conversation earlier than most people expect
• The difference between traditional long-term care insurance and newer hybrid options
• Practical alternatives to insurance, including self-funding and housing-based strategies

This episode offers a calm, realistic framework for approaching a difficult topic and encourages listeners to plan ahead before long-term care becomes an urgent decision.

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

If you’ve ever looked at a successful woman and wondered how she really built it — you’re not alone. Behind every thriving business is a story that doesn’t always show up on social media.

In this episode, Melissa Joy, CFP®, talks with Veronica McGibney, creator of LeadHer Magazine, a new print and digital publication dedicated to sharing the real, behind-the-scenes journeys of female founders.

Veronica shares how a moment of clarity at a business retreat sparked the creation of Lead Her, and how that idea quickly grew into a platform spotlighting women’s honest experiences — from uncertainty and burnout to growth, resilience, and long-term vision. Together, Melissa and Veronica discuss why branding is more than marketing, how visibility impacts opportunity and funding, and why telling the full story matters for women building businesses today.

You’ll learn:

• Why branding plays a critical role in both business growth and personal clarity
• How moments of uncertainty can signal it’s time to pivot or reassess
• What inspired the creation of Lead Her Magazine and its mission
• The realities women founders face that often stay behind the scenes
• Why visibility remains a challenge for women-led businesses
• Practical ways founders manage time, priorities, and competing responsibilities

If you’re building something, considering a pivot, or looking for a more honest picture of what success really takes, this conversation offers insight and perspective.

Resources:

• Learn more about Lead Her Magazine: leadhermagazine.com 
• Connect with Veronica McGibney on LinkedIn: https://www.linkedin.com/in/veronicamcgibney
• Follow Lead Her Magazine on Instagram:  https://www.instagram.com/leadhermagazine/

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

As the new year begins, Melissa Joy, CFP®, helps listeners slow down and reset before diving into financial to-do lists.

In this solo episode, Melissa lays out seven financial planning themes to help guide decisions in 2026. After an intense year of headlines, market shifts, and economic noise, this conversation offers perspective and grounding for those navigating what she calls the “messy money middle.”

Rather than reacting to the news cycle or trying to predict the future, Melissa focuses on practical planning themes — from diversification and human capital to tax changes, estate planning, and lifestyle pressures — all designed to help listeners approach the year ahead with clarity and flexibility.

This episode is meant to level-set expectations and provide a thoughtful framework for anticipating a successful year with your money.

In this episode, Melissa explores:

• Why diversification and rebalancing matter after a strong year for markets
• How international stocks, alternatives, and AI are shaping investment conversations
• Protecting your human capital and preparing for potential job disruptions
• Evaluating the return on investment when spending on skills and career development
• Key tax law changes and what they may mean for planning in the year ahead
• Updates to retirement catch-up contributions and charitable giving rules
• Why estate planning still matters, even when estate taxes may not apply
• How declining interest rates affect cash, savings, and investment decisions
• Determining how much cash to keep versus invest
• Navigating lifestyle inflation and the financial realities of the sandwich generation

The previous presentation by PEARL PLANNING was intended for general information purposes only.  No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...