Dennis O’Keefe
Dennis knew what he wanted to do with his life from junior year in high school. His desire to become a financial planner led him to a Finance degree from Bentley University. For the last 30 years, he has worked with individuals preparing for retirement. He has taught thousands and held the hands of literally hundreds during the often-difficult process of retiring. Dennis holds his CFP(r) designation and has been seen in publications such as The Boston Globe, Yahoo Finance and Business Insider. Learn more here .
Articles by Dennis O’Keefe
- Money & Life
Financial Advice Sounds Simple Until It Costs You
Give us a clean explanation, a confident voice, and a little urgency, and most of us are at least tempted to believe it.
- Money & Life
College Planning Has Changed and Many Families Are Still Stuck in Old Assumptions
What it does mean is that parents shouldn’t automatically assume they will be paying full price.
- Money & Life
What Future Changes Could Mean for Your Social Security Benefits
How policy changes like tax increases or benefit adjustments may shape the future, helping listeners better understand their options and expectations.
- Money & Life
What You Need to Know Before Filing Your 2026 Taxes
Taking a strategic approach to tax planning throughout the year can save you money and eliminate unpleasant surprises when April rolls around.
- Money & Life
Modern Scams, Timeless Tricks: How To Spot Fraud Before It Costs You
They change their shape, but not their essence. Here’s how to recognize the patterns before they get to your wallet or to someone you love.
- Retirement & Income Planning
Voluntary Retirement Offers Explained: How To Decide if It’s the Right Move
How companies carefully craft these packages to achieve specific workforce reductions and shares insights from HR professionals
- Retirement & Income Planning
Severance Now or Separation Later: Making the Call Before the Window Closes
Unfortunately, firms don’t always share their facts and figures with us – making this decision even more difficult.
- Money & Life
The One Simple Tech Change That Can Cut Fraud Risk by 95%
Breaks down how con artists prey on emotion, urgency, and trust and how you can protect yourself and the people you love.
- Money & Life
Why Long-Term Care Is the Most Misunderstood Risk in Financial Planning
Planning for long-term care is one of the hardest and most personal financial challenges families face.
- Money & Life
Laid off or Offered Early Retirement? Here’s the First Thing You Must Do
How prepared you are for this qualifying life event, it can be stressful. Here are a few key areas to concentrate on when crafting your own plan.
- Money & Life
Retirement Offer on the Table? The Hidden Tax Traps and Timing Decisions You Can’t Afford To Miss
What to consider before signing a severance agreement, the hidden tax implications many overlook, and why COBRA coverage may not be your best option.
- Money & Life
The Roth Conversion Mistake That Could Cost Your Heirs Hundreds of Thousands
It might be the wrong move entirely or the right move for the wrong reasons. It all depends on your situation and your goals.
- Money & Life
Beyond Nursing Homes: Understanding the 4 Levels of Modern Elder Care
Four levels of elder care today: home care, senior living, assisted living, and nursing homes, and explains what each one actually means
- Money & Life
Planning for Your Future (And Your Parents’): Understanding Today’s Long-Term Care Landscape
If you’re helping aging parents or thinking about your own future even if you’re only in your 50s, this is for you.
- Retirement & Income Planning
Healthcare Inflation Is Coming for Your Retirement—Here’s How To Fight Back
One of the most confusing and emotionally charged questions in retirement planning: Why is healthcare so expensive, and where is all that money going?
- Money & Life
Why Is U.S. Healthcare So Expensive? Start by Looking in the Mirror
How can the medical industry being facing financial crisis when our costs continue to rise? Where is the money going?
- Money & Life
Beyond Retirement: How To Prepare Now for Care, Housing, and Dignity Later
Why thinking conceptually about your future needs before jumping into legal documents or strategies lays the foundation for confident, compassionate
- Money & Life
Hard Choices Ahead: How To Talk to Your Kids About the Future They’re Walking Into
Not only will this change our children’s spending habits, it might change the face of America in years to come.
- Retirement & Income Planning
Why Debt Could Be the Biggest Threat to Your Retirement Dreams
What if the greatest threat to your retirement isn’t your income, savings, or investments, but your debt?
- Money & Life
Greed and Fear: The Two Emotions That Can Wreck Your Portfolio
Retirement planning can often feel like navigating a complex maze, especially in the face of unpredictable financial markets.
- Retirement & Income Planning
Retirement Anxiety Is Real—Here’s How to Beat It for Good
Many other life events, retirement is a one-time decision that’s often irreversible, making thoughtful planning absolutely essential. #Retirement
- Retirement & Income Planning
The Power of Living Trusts: Protect Your Assets and Your Legacy
Sheds light on the intricacies of living trusts and how they can become a vital component of your retirement planning strategy. #Retirement
- Money & Life
From Paycheck to Prosperity: Unlock the Secrets of Effective Financial Planning
Been retired for years or on the verge of retirement, or are wondering how to plan for your someday retirement, this podcast is your go-to guide.
- Future of Advice
Automated Investing: Is It Right for You? The Pros & Cons
The world of automated investment management and the critical differences between computer and personal touch in retirement planning.
