If you’ve been hearing more talk about health insurance costs lately — you’re not alone. From higher renewal premiums to open enrollment decisions, healthcare has become one of the biggest line items in many household budgets.

In this episode, Melissa Joy, CFP®, talks with Cole Craven, co-founder of Move Health, about what’s really happening with health insurance in 2025 and how to make confident decisions for your family or your retirement.

Cole works closely with financial planners to help clients understand their options, and he shares practical insights you can use right now — whether you’re choosing coverage through your employer, the marketplace, or looking ahead to early retirement.

You’ll learn:

• What’s driving healthcare costs higher in 2025
• How the Affordable Care Act (ACA) marketplace actually works
• The difference between COBRA, private plans, and marketplace coverage
• What to know about tax credits (and what might change next year)
• Why planning for healthcare is essential if you’re retiring before 65
• How to find the right help during open enrollment

If you’ve ever said “I’d retire early if it weren’t for health insurance,” this conversation is for you.

Resources:

• Learn more about Move Health: advisors.movehealth.io
• Connect with Cole: https://www.linkedin.com/in/cole-craven/,
• Follow Move Health https://www.linkedin.com/company/move-health-partners

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 if you could give your kids a real head start—not just for college, but for life?

Melissa Joy, CFP®, sits down with fintech founder Philip Barrar to talk about building generational wealth the modern way—through financial literacy, access, and the right tools.

Philip shares how his company, Future Money, is helping families create a foundation for financial security—no trust fund required. From innovative accounts like the Junior Roth IRA™ (a 529-to-Roth pathway) to new “Trump Accounts” launching under the SECURE 2.0 Act, they explore how technology is democratizing wealth-building for everyday families.

Melissa and Philip also dig into:

• 💬 Why conversations about money at home matter more than ever
• 💸 How to make financial tools accessible without needing a million dollars first
• 🧠 Lessons in financial confidence for parents and kids
• 📈 New, tax-advantaged ways to invest for your child’s future

Together, they reframe generational wealth as something inclusive, intentional, and deeply personal—a legacy built not only on dollars, but on knowledge and confidence.

Connect with Philip:

https://www.futuremoney.co/

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

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 if your money mindset mattered as much as your money habits? 💭

This week, Melissa sits down with Aja Evans, licensed mental health professional, president of the Financial Therapy Association, and author of Feel Good Finance, to explore how emotions, upbringing, and self-worth shape the way we earn, spend, and save.

Together, they unpack how to identify your money story, recognize emotional spending triggers, and find balance between saving, spending, and satisfaction. From “Target trips gone wild” to understanding the dopamine behind shopping, Aja explains why awareness—not shame—is the first step toward financial peace.

You’ll learn how to:
💡 Uncover emotional roots behind your money habits
💡 Reframe guilt or scarcity into confidence and clarity
💡 Recognize when spending is self-care vs. self-sabotage
💡 Build a “feel-good” financial plan rooted in contentment, not comparison

Whether you overspend, underspend, or just want a healthier money mindset, this episode will help you bring a little more feel-good into your finances.

📘 Learn more about Aja’s work:

Connect on IG: @ajaetherapy

Connect on LinkedIn: https://www.linkedin.com/in/ajaevans/

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 money dynamics shift inside a relationship—and how do couples find fairness when life, careers, and income change?

In this episode, Melissa Joy, CFP® sits down with Heather and Douglas Boneparth, the powerhouse couple behind Money Together: How to Find Fairness in Your Relationship and Become an Unstoppable Financial Team.

Heather, a former corporate lawyer, and Douglas, founder of Bonafide Wealth in New York City, open up about how their own experiences as partners, parents, and business owners inspired the book—and why talking about money as a team is harder (and more important) than ever.

Together, they explore:

• ⚖️ How power dynamics around money evolve over time—and what couples can do to keep conversations fair and balanced
• 💬 Why curiosity and communication are the foundation of financial teamwork
• 💡 The “aha” moments from interviewing 75+ couples about love, money, and identity
• ❤️ Why fairness doesn’t always mean 50/50—and how to navigate changing roles without resentment
• 🧩 The link between our upbringing, money habits, and emotional reactions in financial conversations
• 📖 What they learned from writing the book together—and how it reshaped their own partnership

Melissa and her guests also discuss what advisors can take away from Money Together: how to see both partners equally, ask better questions, and help clients build stronger financial relationships—not just portfolios.

✨ Whether you’re managing finances solo or as part of a couple, this conversation reminds us that money isn’t just math—it’s meaning, emotion, and teamwork.

📚 Learn more:
Money Together: How to Find Fairness in Your Relationship and Become an Unstoppable Financial Team
👉 www.domoneytogether.com
👉 www.readthejointaccount.com

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:...

How do you help your kids get into the right college—without sacrificing your financial future?

Melissa Joy, CFP®, sits down with Shellee Howard, Founder and CEO of College Ready, to talk about smart, stress-free strategies for college admissions and funding.

A certified college admissions strategist, Shellee turned her own experience guiding four very different kids through the college process into a mission: helping families nationwide find the best academic, social, and financial fit. From creating a standout student profile to uncovering hidden scholarship opportunities, Shellee shares how to approach college planning with clarity, confidence, and strategy.

💡 Key Takeaways:

• Why college admissions should be approached like a business decision.
• The three funding mindsets: writing the check, earning scholarships, or finding schools that pay for your student.
• What FAFSA actually looks at—and why timing matters.
• How to find real, essay-based scholarships (and avoid scams).
• The “Millionaire Game” exercise to help your teen discover what drives them.
• Why the right fit school is more valuable than a “dream” school with a big price tag.

Shellee’s insights from College Ready help parents and students reduce stress, minimize debt, and make informed, values-based decisions about higher education.

🔗 Resources Mentioned:

• College Ready — Learn more about services, free consultations, and resources.
• Podcast: Parents, Is Your Teen College Ready?
• Books by Shellee Howard, 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:...

What if knowing your worth became the engine of your wealth?

Strategist and former credit-union executive Bryn Conway joins Melissa Joy, CFP® for a candid, practical conversation about women, wealth, and worth—why the gaps persist and how to close them with informed choices, confident negotiation, and everyday money moves.

Bryn breaks down the landscape—pay, advancement, earnings, and wealth—and how culture, career paths, and compensation structures (including equity) shape outcomes. She shares simple, repeatable actions: normalize money conversations, apply before you feel “100% ready,” negotiate every offer, and “pay future-you first.” Melissa adds planner-level insights on using a financial plan to manage your human capital—from asking for more to aligning your role with your goals.

Together, Bryn and Melissa reframe the path forward: turn passive awareness into active steps that compound over time, build resilience, and help women advance—at work and in wealth.

This episode is a reminder that your value isn’t just recognized—it’s negotiated, nurtured, and compounded.

💡 Key Themes Covered:

• The four gaps women face: pay, advancement/opportunity, lifetime earnings, and wealth
• Why roles, sectors, and equity compensation widen outcomes—and how to navigate them
• “Apply anyway”: closing the confidence gap and raising your hand before you feel ready
• Negotiation playbook: know the comps, make a specific ask, and revisit review/raise cadence
• “Pay future-you first”: enroll in the match and send half of every raise to long-term savings
• Normalize money talks: mentors, sponsors, and transparent check-ins that build confidence and change results

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 if planning now could be the greatest act of care?

Journalist and MarketWatch columnist Beth Pinsker joins Melissa Joy, CFP® for a compassionate, practical conversation on financial caregiving—the real work we do for the people we love (and our future selves). Beth opens up about the whirlwind that followed her mom’s surgery: hospital stays, paperwork marathons, and a long-term care scare that nearly derailed benefits. Through her new book, My Mother’s Money: A Guide to Financial Caregiving, she lays out a simple roadmap—documents to have before a crisis, a one-page medical “cheat sheet,” and why simplifying accounts and beneficiaries might be the most loving step you take this year.

Together, Beth and Melissa unpack how to connect the legal, medical, and financial lanes so caregivers can act quickly (and confidently). From the $100 POA that can save $18,000+ and a year of guardianship hassles, to making sure trusted contacts and online access are current, this episode turns overwhelm into a plan.

This is your nudge: fear and uncertainty are inevitable—but you can still take control of the plan.

💡 Key Themes Covered

• How a simple medical + contacts cheat sheet can save precious time in emergencies
• The “$100 vs. $18,000” reality: POA/healthcare proxy/HIPAA before a crisis vs. guardianship later
• Why women often shoulder caregiving—and how to prepare even if you’re not the household “money person”
• Long-term care pitfalls (missed paperwork, past-due notices) and how to prevent coverage lapses
• Simplify to protect: consolidate old 401(k)s, confirm beneficiaries/TODs, set legacy/phone access
• The caregiver wallet: cash-flowing expenses, reimbursement timelines, and organizing receipts
• Conversation starters with parents, partners, and siblings to align on roles and next steps

Connect with Beth Pinsker

🔗 LinkedIn: linkedin.com/in/bpinsker

🌐 Bluesky: bsky.app/profile/bethpinsker.bsky.social

📸 Instagram: @bethpinsker_ny

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:...

Fall isn’t just for cider mills, football games, and cozy sweaters—it’s also the perfect season to reset your financial life. In this solo episode, Melissa Joy shares seven practical tips to help you take advantage of seasonal opportunities and set yourself up for success before the year ends.

From open enrollment decisions and maximizing workplace benefits to planning for holiday spending, reviewing your investments, and checking in on your estate plan—Melissa walks through the steps that can help you move forward with clarity and confidence.

You’ll learn how to:

• Make the most of your employer benefits and avoid last-minute enrollment stress
• Use remaining 2025 benefits wisely, from FSA dollars to legal perks
• Take proactive steps on taxes before December 31
• Plan and budget for the holidays to avoid year-end financial regret
• Rebalance your portfolio and revisit investment opportunities
• Update beneficiaries, life insurance, and estate planning documents
• Conduct a fall financial health check and set goals for the new year

As Melissa reminds us, progress is always more important than perfection. Pick one or two of these seasonal money tasks, get them done, and set the tone for a stronger financial future.

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:...