Medicare open enrollment is almost here, and this year it’s shaping up to be one of the most dramatic seasons ever. Millions of retirees are about to lose their Advantage plans or face major changes, while even those with traditional Medicare supplements could see higher costs ahead. In this episode, Don breaks down the why, what, when, and how of the Medicare shakeup.

Here’s some of what we discuss in this episode:

🍂 Medicare open enrollment runs Oct 15 – Dec 7

⚖️ Understanding Medicare Advantage vs. Supplement

🚨 2 million people losing Advantage coverage this year

💊 Rising medical & prescription costs driving plan changes

📝 Don’s “3 M’s”: Mail, Map, and Math

Get in touch with Don and learn more: https://doncashpodcast.com/

Planning for retirement comes with a flood of questions, some about taxes, others about investments, and often about protecting your family. Today, Don breaks down New Jersey’s new property tax relief program, explains how it bundles multiple programs into one, and shares what you need to know before the October 31st deadline. Don also weighs in on life insurance, when it’s a useful tool for family protection and estate planning, and when it’s just another aggressive sales pitch.

Tune in to hear Don's insights on these topics and more in this week's listener question episode!

Here’s some of what we discuss in this episode:

🏠 Decoding NJ property tax relief programs

💡 Smart questions to ask before buying life insurance

📈 Turning decades of savings into a retirement strategy

🔑 Why discipline and purpose matter more than timing the market

Get in touch with Don and learn more: https://doncashpodcast.com/

Feeling the squeeze of inflation? Even as headlines say it’s “cooling,” prices at the grocery store, restaurants, and on vacation aren’t letting up. In this episode, Don breaks down the paradox retirees face today: interest rates may be dropping, but the cost of living isn’t.

Here’s some of what we discuss in this episode:

💸 Why inflation still feels “sticky” even when the government says it’s easing

🏥 How inflation impacts healthcare, drug costs and Medicare premiums

🏠 How the generational divide impacts finances differently for millennials vs. retirees

📉 What lower interest rates mean for your savings and CDs

📊 How diversification, tax planning, and estate strategies can protect your future

Get in touch with Don and learn more: https://doncashpodcast.com/

Estate planning rules can be complex and costly if you miss a key step. In this episode, Don explains how recent changes to the estate tax exemption could impact your legacy, and why the term “permanent” in Washington rarely means forever. You’ll learn about the important concept of portability (preserving your late spouse’s unused estate tax exemption) and why filing the right form, even when no tax is owed, can save you millions.

Here’s some of what we discuss in this episode:

💰 Understand new estate tax exemption limits

🔄 Learn how portability works (and why deadlines matter)

🏦 Avoid costly filing mistakes that can erase tax savings

📉 Real case: $1.5M lost due to one oversight

📝 Key documents every 18+ year-old should have

The pros and cons of portability –

https://taxschool.illinois.edu/post/pros-and-cons-of-portability/

The Wall Street Journal Article - $1.5 million portability mistake

https://www.wsj.com/personal-finance/taxes/estate-taxes-portability-planning-mistakes-26111632?st=AbePZ6&reflink=desktopwebshare_permalink

Get in touch with Don and learn more: https://doncashpodcast.com/

This week, we’re back to take a deeper dive into the One Big Beautiful Bill (OBBB). Don breaks down how this sweeping legislation impacts standard deductions, estate taxes, Roth conversions, charitable giving, and more. Tune in to learn why the years 2025–2028 might be your “golden window” for smart, tax-efficient planning, and how to take full advantage of it.

Here’s some of what we discuss in this episode:

💸 Extra deduction opportunities after age 65

🏡 Estate tax changes that benefit most retirees

🔁 Strategic Roth conversion window until 2028

💰 Avoiding costly Medicare surcharges

🧾 The hidden costs of becoming a single filer

Get in touch with Don and learn more: https://doncashpodcast.com/

A new tax bill has officially passed (you’ve probably heard it mentioned as the “Big Beautiful Bill”). In this episode, Don breaks down what the newly signed bill actually means for retirees, pre-retirees, and anyone planning for their financial future. While the bill made headlines for its timing and optics, the real story lies in the planning opportunities it creates. Don walks through key updates, including the extension of current tax brackets, a higher SALT deduction cap, a new senior bonus deduction, and strategic opportunities for Roth conversions.

Here’s some of what we discuss in this episode:

🧾 What “permanent” really means in Washington tax law

📊 Extended tax brackets offer a rare window for low-tax Roth conversions

🧾 SALT deduction cap raised from $10K to $40K

💸 The new $12K “senior deduction” and its impact on Social Security taxes

💰 Estate tax exemption raised to $15M

⏳ Why 2028 could be a critical planning deadline

Get in touch with Don and learn more: https://doncashpodcast.com/

There’s a lot happening in the world right now- but quietly moving through Congress and the Senate is a major new tax bill. If passed, it could have a significant impact on retirees, investors, and families with larger estates. In this episode of Your Money and Your Life, Don breaks down the key provisions you need to know.

Here’s some of what we discuss in this episode:

📉 Proposed tax breaks for retirees over 65

🧾 Why Social Security is still taxable under the new bill

🏥 Medicaid changes and how they may (or may not) affect long-term care

🏛️ Clearing up confusion on potential estate tax updates

💡Cash Corner: planning moves to protect what you love

Resources for this episode:

New Jersey’s Estate and Inheritance Tax Episode:

https://yourmoneyyourlife.podbean.com/e/the-2025-social-security-increase-new-jersey-triple-tax-benefit/

Get in touch with Don and learn more: https://doncashpodcast.com/

We’ve all heard of FOMO: fear of missing out. But in 2025, a new investor emotion is taking center stage: FOGI, the fear of getting in. After watching market volatility, political headlines, and wild swings in interest rates, many investors are stuck sitting on the sidelines, afraid to buy back in, afraid to buy too late, and most of all, afraid of looking foolish. It’s not just about risk anymore. It’s about regret.

In this episode, Don discusses the emotional roadblocks keeping investors frozen, including timing fatigue and media panic cycles.

Here’s some of what we discuss in this episode:

🌀 What is FOGI and how it’s different from FOMO

💣 Why timing the market is so tempting… and so damaging

📢 The impact of media noise and headlines

🎯 What smart investors do instead of chasing or fleeing

🔄 Real strategies for getting back in without regret

Get in touch with Don and learn more: https://doncashpodcast.com/