Retirement is one of the most talked about financial milestones, but the concept of retirement itself, what it looks like, how it feels, and how to actually envision it, often goes unexplored. Melissa Joy, CFP® sits down with Jamie Hopkins, CEO of Bryn Mawr Trust, and Bonnie Treichel, CEO of Endeavor Retirement, to talk about their new book, Your Retirement Sketchbook. Equal parts workbook, coffee table book, and retirement roadmap, it covers 125 snackable concepts designed to help readers think about retirement in a whole new way.

From vision boards to estate planning, adaptive spending strategies to the emotional side of leaving a career behind, Jamie and Bonnie bring both the technical and the human side of retirement planning into focus. This is a conversation for anyone who wants to move beyond the spreadsheet and actually picture what retirement can look like for them.

What You'll Learn

• Why most people build their retirement vision from someone else's experience and why that creates problems
• How planning toward averages, including average life expectancy, can lead you astray
• What adaptive retirement planning is and why it better reflects how people actually live
• Why many retirees with significant savings actually underspend and how to give yourself permission to enjoy what you have built
• How retirement vision boards work and why putting yourself on the board changes everything
• Why your relationship with money follows you into retirement and how the book addresses that head on
• What the sketchbook concept means and how the book invites you to evolve your plan over time
• Why end of life planning remains the most overlooked piece of retirement and what to do about it
• How Jamie and Bonnie each updated their own estate plans while writing the book

Connect with Jamie: www.bmt.com

https://www.linkedin.com/in/jamiehopkinsfinancialservices

Connect with Bonnie: www.endeavor-retirement.com

IG: @retirementrisks

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...

Teaching kids about money is one of the most important things we can do as parents, but it's also one of the most overlooked. Melissa Joy, CFP® sits down with returning guest Charlotte Geletka, CFP® and owner of Silver Penny Financial Planning, to talk financial literacy at every age and the charming children's book she co-authored with her 12 year old son, Battery, the Bulldog and the Funny Money Tree, released on March 17th.

From tooth fairy moments to teenager debit cards to the real cost of college debt, Charlotte breaks down how money conversations can and should evolve as children grow. She and Melissa explore the dangers of TikTok financial advice, the gamification of investing, and why conscious spending beats the YOLO mentality every time.

What You'll Learn

• How children begin forming money concepts earlier than most parents realize
• Why giving small kids cash to spend at the store is one of the best financial literacy tools around
• How kid friendly debit cards like Greenlight are teaching real world money management in middle and high school
• Why TikTok financial advice and gamified investing apps are a growing concern for parents
• How to have honest conversations with your kids about income, debt, and what things actually cost
• Why the financial decisions made in your early twenties have an outsized impact on the rest of your life
• The difference between payment focused thinking and understanding the true cost of credit
• How Charlotte and her son Andrew created Battery, the Bulldog and the Funny Money Tree together and what it took to get it published

Connect with Charlotte: Instagram: @silverpennyfinancial

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

Book: Battery, the Bulldog and the Funny Money Tree: https://littleripples.media/books/battery-the-bulldog-and-the-funny-money-tree

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 does it look like when financial planning meets love, courage, and intentional family leadership? Melissa Joy, CFP® sits down with Shelby Nicholl, founder of Muriel Consulting, to share the story of her father-in-law's remarkable family meeting, held just weeks before his passing. From a handout at the table to a hug at the end, this episode is a powerful reminder that clarity is one of the greatest gifts we can give the people we love.

Papa Harry didn't wait for the hard conversations to find him. When he learned his illness was terminal, he went into action. A new roof, a clean garage, and a carefully prepared Sunday evening meeting with handouts and pens. What unfolded was one of the most organized, loving, and generous acts a parent can offer their family, and a masterclass in what it looks like to lead with both heart and intention.

What You'll Learn

• Why family meetings matter and how to structure one before a crisis hits
• How one family organized passwords, daily bills, and account access in a single sitting
• What medical directives really mean and the nuanced questions families often miss
• How to talk about wealth, legacy, and inheritance in a way that feels natural and generous
• Why beneficiary designations deserve a second look, especially for DIY investors
• How to think about bringing in a financial advisor during a transition of responsibility
• What family governance can look like beyond dollars and cents
• How one family meeting set the tone for values, communication, and stewardship across generations

Connect with Shelby:

www.murielconsulting.com

https://www.linkedin.com/in/shelbynicholl/

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...

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...