Regarding Retirement

What can retirees learn from Warren Buffett stepping away at 95? In this episode, Neil Henry revisits the timeless investing principles behind Buffett’s success and how they apply to retirement planning today. The conversation explores why long-term ownership of quality investments often outperforms chasing trends, and how emotional decision-making can derail even the best intentions. Neil a...

What happens to your retirement plan when “we” suddenly becomes “me”? In this episode of Regarding Retirement , Neil Henry explores the growing reality of solo aging and why planning for it is no longer optional. He discusses how losing a spouse can impact income streams, Social Security, pensions, and daily decision-making—and why proactive planning matters long befo...

Is using your retirement savings to buy a home solving today’s problem or creating tomorrow’s? In this episode, Neil Henry explores a proposal allowing penalty-free 401(k) withdrawals for home purchases and what it could mean for long-term financial security. He breaks down the trade-offs between homeownership and retirement savings, including taxes, lost compounding growth, and the ri...

Should working one more year before retirement be a smart move—or a costly sacrifice of time you won’t get back? In this episode of  Regarding Retirement , financial planner Neil Henry unpacks the real‑world factors behind the “just one more year” decision. Using recent headlines and practical client examples, he explores how timing retirement impacts savings, Social S...

Even with solid savings, many retirees worry more about running out of money than enjoying what they’ve built. In this episode of  Regarding Retirement , financial planner Neil Henry tackles the fear that quietly follows many retirees into their next chapter. The conversation explores why anxiety persists regardless of net worth, how establishing clear income “knowns” can ea...

A new government‑backed savings program for kids is generating buzz—and plenty of questions from parents and grandparents. In this episode, host Neil Henry, financial planner and founder of Henry and Associates, breaks down what we currently know about the new “Trump Accounts for Kids.” He discusses who qualifies, how the accounts may be funded, how they compare to 529 plans, and...

What if a few overlooked tax details could quietly impact your retirement income this year? In this episode, host Neil Henry, financial planner and founder of Henry and Associates in Charleston, South Carolina, breaks down a practical tax‑season checklist for retirees and pre‑retirees. He discusses recent tax law changes affecting Social Security, higher standard deductions for retirees, and why t...

Annuities are widely used — yet often misunderstood. In this episode of Regarding Retirement , financial planner Neil Henry breaks down why annuities generate so much confusion and how different types serve very different purposes. The conversation explores fixed, indexed, and variable annuities, common misconceptions fueled by media coverage, and why liquidity, fees, and income structure ma...

Your retirement fears may have less to do with markets — and more to do with your past. In this episode, financial advisor Neil Henry explores how emotional “money baggage” shapes retirement decisions, from childhood beliefs to lived experiences like market downturns and income loss. The conversation looks at how fear, control, and uncertainty often surface as people transition f...

Preparing for major health and long‑term care costs becomes unavoidable as retirement approaches, and this episode digs into what those realities truly look like. Neil Henry explores the rising expenses tied to Medicare, supplements, prescriptions, and the long‑term care needs many retirees eventually encounter. He shares real‑life examples, breaks down average cost expectations, and discusses why...

Big tax shifts are landing in 2026, and they could reshape how retirees manage income, investments, and long‑term planning. In this episode, financial advisor Neil Henry breaks down the new standard deduction amounts, updated tax brackets, and what seniors should understand about RMDs as withdrawal percentages rise with age. He also sheds light on capital gains thresholds and why today’s low...

Trillions are changing hands in the greatest wealth transfer of our time, and women are set to inherit nearly 70% of it. But with new opportunities come unique challenges—especially for those suddenly thrust into financial decision-making. In this episode, financial planner Neil Henry explores how women can confidently navigate inheritance, longevity, and retirement planning. Learn why 80% o...

Ever tried to save money, only to spend more than you planned? Discover the sneaky world of “spaving”—and how these habits could quietly sabotage your retirement. Host and financial planner Neil Henry unpacks hidden fees, budgeting myths, and why relying on Uncle Ed’s advice might leave you short. Learn how a personalized financial plan can turn budgeting from a dreaded cho...

What drives a financial planner to help others live to 100? In this episode, Neil Henry shares the story behind Henry & Associates, his passion for serving Charleston’s retirees, and the wisdom gained from decades of guiding clients through life’s biggest transitions. Discover how Neil’s personal journey shapes his approach, why community matters, and the advice he wishes eve...

Are you ready to make the most of Medicare Open Enrollment? In this episode, Neil Henry shares decades of experience guiding retirees through the maze of Medicare choices, from Parts A, B, and D to Medigap and Advantage plans. Discover the most important decisions for newcomers, common mistakes to avoid, and how to review your coverage as your health needs change. Neil breaks down complex rules, o...

Neil Henry talks about long-term care and how people often underestimate its cost. He shares stats of how many people need LTC (and how this is sometimes temporary) and what the different types are. Neil also compares the rough costs of the different phases of that care and shares a story about how a person with proper coverage saved themselves tens of thousands of dollars. Neil also talks about t...

Neil Henry discusses Medicare and explains the age that most people are eligible for it and how long before then that they should apply for the coverage. He also shares what Plan A & B plans are, what Medicare Advantage is, and what other costs people need to plan for. Neil also discusses what he sees as some good political news that is also shaping the market. Schedule your complimentary cons...

Neil Henry discusses how inflation can wreck retirement income, if people are not careful. He emphasizes the importance of making a plan and how he factors in certain increases over time, so people can have a plan for money to outlive them. Neil also talks about using annuities and other tools to dispense this income and also how taxes can really bit people if they do not plan for them. Schedule a...

Neil Henry returns to talk about something that has become a bigger staple in retirement portfolios: annuities. Neil explains the different kind of annuities and how certain kinds have given all of them bad names. Neil describes how to build a retirement income plan and why annuities have gotten more popular in recent years. Schedule a complimentary consultation to work on a plan to help secure yo...

Neil Henry breaks down Medicare for listeners and talks about plans A, B, C, and D and what  Medigap and Medicare Supplement Insurance are. Neil also gives the pros and cons of the Medicare Advantage Plan and some examples of how that can work against a person's best interests. He talks about his holiday plans and if he likes to sail his boat in cold weather.  Ready to connect with Neil?...

Neil Henry discusses the results of the presidential election and how Trump's victory will affect any current or future tax cuts. Neil also talks about wonky job numbers, future government job cuts, and how all of that can affect the economy. Ready to connect with Neil? Visit his website today! See omnystudio.com/listener for privacy information.

Henry and Associates founder and financial planner Neil Henry discusses what RMDs are and how both they and their tax implications can surprise people. Neil breaks down the method he uses to prepare clients for this and which retirement accounts RMDs impact. He also describes his love for sailing and the big steps he took to protect his sailboat before Hurricane Helene struck South Carolina. Ready...

Neil shares his insights on how inflation affects retirement planning and what strategies can help retirees cope with rising prices. He explains why fixed rate annuities are an attractive option for retirees who want to lock in high interest rates and secure a steady income for life. He also discusses how annuities can diversify one's portfolio and reduce exposure to market volatility and tax liab...

The conversation discusses the impact of taxes on retirement planning and starts with a discussion about whether American athletes have to pay taxes on the medals they win at the Olympics. The conversation then delves into various forms of income that can be taxed during retirement, such as Social Security, interest-bearing accounts, sales of stocks and bonds, and withdrawals from traditional IRAs...

Everyone dreams of retirement, but all the perks and daily activities of the lifestyle still require funding, which means you’ll have to provide your own paychecks in your golden years. That’s where “Regarding Retirement” steps in. Hosted by Neil Henry of Henry and Associates, this podcast offers a steady and timely stream of advice and insight focused on how you are approaching saving for (and sp...