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You can do everything right and still feel stuck. Save aggressively. Max out your 401k. Build a large portfolio. And then one day realize you can’t actually use it when you want to. In this episode, J...
As you get close to retirement, something unexpected starts to happen. The math looks good. The plan works. And yet, you hesitate. In this episode, James Conole explores the quiet mental traps that sh...
One of the biggest fears people carry into retirement is running out of money. But for many retirees, the greater risk is something else entirely. Running out of time. In this episode, James Conole, C...
What if the strategy you trust most for retirement income is quietly costing you hundreds of thousands of dollars? Topics covered in this episode: The real driver behind outperformance Sequence of ret...
Roger Whitney breaks down how to create a diversified portfolio by explaining the core principles of diversification and asset allocation, then answers listener questions on topics like using allocati...
"Chase and Ryder" are 56 and 55 with $5 million saved and huge pensions the day they retire. So why are they so nervous about pulling the trigger? That's today on Your Money, Your Wealth® podcast numb...
Football can teach retirement investors a lot about managing risk. And if predictions of a markets slump are accurate, one strategy will be particularly useful.
When I was younger, I had a simple budgeting strategy for making decisions. I called it my trifecta theory. If something checked three boxes… Financially smart, Personally beneficial, and Efficient […...
Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether a popular early retirement strategy could actually blow up your financial plan, today on Your Money, Your Wealth® podcast number 577. Red...
Too rich for basic financial advice but not rich enough for private client services? What's the best way to plug the "middle wealthy" retirement planning gap?
Planning to live to 95? Why your retirement strategy needs a 'healthspan' reset.
Oil and gas investments can play a lasting role in a diversified portfolio, but be sure to consider how they fit into your broader strategy and estate plan.
In this episode of the Retirement Answer Man, Roger Whitney explores the critical decision of when to claim Social Security benefits, weighing the pros and cons of taking them early versus delaying. T...
Are Roth conversions worth it? We'll find out, today on Your Money, Your Wealth® podcast number 576. TJ in PA is gonna have huge capital gains. Joe and Big Al spitball on whether it's worth it for him...
Brigadier General Michael Meese details the critical decisions military families must make before retirement. Transitioning into retirement is a major life change for anyone. But for military families...
Most people think retirement begins the day they turn in their notice. In reality, retirement begins much earlier than that. It begins the moment you stop depending on your employer for everything. In...
“Only live off the dividends. Never touch the principal.” It sounds responsible. It feels safe. It may be one of the riskiest retirement strategies out there. In this episode, James breaks down why bu...
Everyone thinks retirement is a permanent vacation. For the first few months, it might feel that way. Then something shifts. The novelty fades. Tuesdays start to feel like Saturdays. The structure tha...
Outliving your money is the real risk. Learn how longevity can quietly derail even the most well planned retirement strategy.
What are Passive Income Generators (PIGs) and Passive Activity Losses (PALs), and how do they interact with each other on your tax bill? The post Using Passive Income Generators (PIGs) to Offset Passi...
Women should personalize their Social Security claiming strategy and run the numbers after considering life expectancy, tax situation and existing assets.
Leslie and Thomas Martin stress-tested their portfolio and gained the confidence to retire with a personalized financial strategy. The post ‘Do We Have Enough?’ How This Couple Knew When to Retire app...
Jeremy Keil explains how putting your cash in the wrong spot could prevent you from earning thousands in interest during your retirement. Many retirees spend a lot of time thinking about how to get be...
Author Ethan Lohr shares how the four buckets retirement income strategy helps retirees behavior-proof their retirement. Many retirees face one similar problem that they struggle to name: the emotiona...
If you convert to a Roth today, could Congress change the rules tomorrow — and should that fear stop you from taking action? In this episode, you'll learn: The truth about retroactive Roth taxation Wh...
Earlier this month, my article The 60/40 Portfolio vs. The Bucket Strategy compared the two approaches since my retirement and generated a LOT of discussion. The Bucket Strategy outperformed by $241k,...
Choosing the best way to withdraw retirement funds depends on which paycheck system aligns with your lifestyle, tax plan and shifts in spending as you age.
Don't just set and forget your 401(k). Creating a plan for investments, income and health care ensures your balance translates into lifelong financial security.
? Show Notes Wade Pfau, author of The Retirement Planning Guidebook and creator of the Retirement Income Style Awareness (RISA®) assessment joins Roger for a wide-ranging conversation on the big quest...
We all know we need to have an emergency fund, mine is around 6-8 months of expenses, but what's your strategy for if and when you dip into it, how do you go about replenishing it when you're on a tig...
Jeremy Keil explains 3 smart ways to help your kids with money while avoiding IRS paperwork Early in the year, I received an email from a couple asking a question I hear all the time: “What’s the maxi...
"Carl and Jane" have eight million bucks, and their advisor is suggesting a 130/30 long-short investing strategy. Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether this is a smart tax mov...
More than half of recent retirees say they regret how they saved, and only 2 in 5 feel on track with their original retirement plan. See what the data reveals and how to stress-test your 401(k) strate...
In this episode, James walks through four of the most common income strategies retirees consider today and why many people are still using outdated math for a 2026 retirement. The question is not just...
When I retired in 2018, I implemented the Bucket Strategy. What would have happened if I had used the 60/40 Portfolio instead? I decided to find out. For today’s post, […] The post The 60/40 Portfolio...
The retirement mindset mentor George Jerjian explains how a second chance at life inspires him to help coach people into retirement. When George Jerjian was 52 years old, he was diagnosed with a bone ...
If you plan to punch the clock for the final time decades before "standard" retirement age, you need a financial strategy that goes beyond just saving. Joe Anderson, CFP® and Big Al Clopine, CPA spitb...
Retiring at 55 is not just retiring ten years earlier. It changes the entire math of your life. From 55 to 65, expenses are often at their highest. You are covering healthcare before Medicare, traveli...
Your spouse wants to remodel your kitchen and several bathrooms in your house. You’ve received a quote for the work for about $100,000. Using a strategic withdrawal approach and a Monte Carlo modeling...
Once you're retired, your focus should shift from maximum growth to strategic preservation and purposeful planning to help safeguard your wealth.
This post is a follow-up to our post of August 23, 2025 where we encouraged financial advisors and DIYers to ditch Monte Carlo modeling and its probability of success metric and adopt the Actuarial Ap...
Roger Whitney wraps up the four-part series on navigating health care before Medicare by introducing a practical decision-making framework using the OODA Loop—observe, orient, decide, act—to help you ...
Jeremy Keil explains the 5 RMD (Required Minimum Distribution) mistakes in Retirement and how to avoid them. A retiree recently called for help. It was their first year taking Required Minimum Distrib...
The first quarter of the year is when most doctors are flush with bonus checks and maybe even a little ... Read more
The final five years before retirement are not maintenance mode. They are leverage years. Small decisions made here can outweigh the previous twenty years of saving and investing. In this episode, Jam...
Happiness expert Monique Rhodes explains why retirement often feels disorienting at first — and how creating a personal retirement roadmap can turn this transition into one of the most fulfilling stag...
Gary Zimmerman of Max® explains how to utilize your cash asset in retirement. Cash is one of the most overlooked assets in retirement. Here’s how retirees can earn thousands more in interest while kee...
Millions of people over 65 care for grandkids, adult kids or aging parents and will also need care themselves. Building a caregiving strategy is crucial.
Most retirees who make this mistake aren’t reckless. They’re careful. They’re doing what they believe is responsible, and that’s what makes it so painful to see when it backfires. James explains why t...
A $10 million retirement is often imagined as the finish line — complete freedom, unlimited spending, and no financial stress. The reality is more complex. James walks through what an eight-figure ret...