Your Successful Retirement
Discover the secrets to a successful retirement with Dennis O’Keefe, a seasoned CERTIFIED FINANCIAL PLANNER™ with over 30 years of expertise. Whether you’ve been retired for years, are on the verge of retirement, or are wondering how to plan for your “some-day” retirement – this podcast is your go-to guide. Gain exclusive strategies tailored to optimizing your retirement benefits, hear real-life stories from retirees, and absorb invaluable wisdom from our guest leaders.
Episodes
Should you convert your traditional IRA to a Roth IRA? In this YSR FAQ episode, Dennis O’Keefe breaks down the pros and cons of Roth conversions and explains why the answer depends heavily on your tax situation.
Dennis discusses how Roth conversions are taxed, the importance of understanding tax brackets, and why many investors benefit from a multi-year co...
How closely should you monitor your retirement accounts?
In this YSR FAQ episode, Dennis O’Keefe explains why both neglecting your 401(k) and obsessively checking it can create problems.
Using examples from his own experience and lessons from past market cycles, Dennis discusses the importance of reviewing accou...
Thinking about buying a car? It can feel overwhelming, especially when prices, financing, trade-offs, and dealership tactics all compete for your attention.
How do you know you’re paying a fair price, and what steps can help you avoid expensive mistakes before you sign?
In this episode, Dennis O’Keefe shar...
A Roth 401(k) can be a powerful retirement savings tool, but is it the right choice for everyone?
In this YSR FAQ episode, Dennis O’Keefe discusses how Roth 401(k) contributions work and the factors that determine whether they make sense for your situation.
The conversation explores current versus future tax bra...
One of the most common retirement questions is also one of the hardest to answer: How much money is enough?
In this YSR FAQ episode, Dennis O’Keefe explains why there is no universal retirement savings target and why your spending habits matter far more than a simple rule of thumb.
Dennis shares a real-life exam...
Trying to predict the market can feel overwhelming when headlines, opinions, and daily volatility are everywhere.
How do you separate meaningful economic signals from distractions? What information actually helps you make better financial decisions over the long term?
In this episode, Dennis O’Keefe shares why market ...
What is a trust, and why do so many families use them in estate planning? In this YSR FAQ episode, Dennis explains the basics of revocable living trusts and how they help simplify estate settlement while avoiding probate.
This conversation covers how trusts are structured, how assets are transferred into a trust, and why many people use trusts to help manage pro...
Should you place your house into an irrevocable trust? In this YSR FAQ episode, Dennis explains why irrevocable trusts can become far more complicated than many people expect.
This conversation covers why families consider irrevocable trusts for nursing home or Medicaid planning, along with the long-term tradeoffs that come with giving up control of property. De...
Estate planning is easy to delay until the people you love are left sorting through the fallout.
What happens when missing documents, wrong beneficiaries, or an unfunded trust create delays, costs, and family stress?
In this episode, Dennis O’Keefe shares hard-earned lessons about estate planning mistakes that can bur...
What exactly is probate, and why do so many families want to avoid it? In this YSR FAQ episode, Dennis explains how the probate process works, where it originated, and why having a will does not automatically keep your estate out of probate court.
Using stories from English history to modern-day estate settlement examples, this episode breaks down why probate ca...
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