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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...
Retiring after age 65 changes the math and the priorities. You have fewer high-energy years, shorter tax planning windows, and RMDs much closer than most people realize. But you also often have higher...
Christian thought he was ready for retirement. He just didn’t realize how heavy the weight had been until he finally set it down. After more than 30 years in a high-stress, always-on role at a global ...
What can our top five Retire With Purpose Podcast episodes of 2025 teach you about avoiding regrets, spending confidently, and living with purpose as you head into 2026? In this episode, we discuss: T...
An "all-asset" strategy would integrate housing wealth and annuities with traditional investments to generate more income and liquid savings for retirees.
Did you know you could triple your 401(k) contributions with a mega backdoor Roth tax planning strategy? We share how to maximize your tax free retirement income.
If your house is too cluttered, it's probably time to do something about it. Decluttering will save you time; space; and, yes, money. The post Decluttering as a Financial Strategy appeared first on Th...
Jeremy Keil explains the 5 steps you can take if you are planning to retire in 2026 or 2027. If you’ve been planning to retire in 2026 or 2027, it might feel like you still have plenty of time. But in...
Jeremy Keil weighs the opportunities and risks associated with giving your money away to your kids and charity. Most retirees I talk with don’t worry about whether they can give money away. They worry...
In this Christmas Eve episode, Roger Whitney explores the basics of charitable giving as part of an intentional retirement plan, with a timely focus on year-end decisions. He explains how charitable d...
Jeremy Keil explains the top 3 tax efficient strategies for charitable giving in 2025. Most people give to charity because it’s meaningful to them — not because of the tax break. And that’s the right ...
Roth conversions can save thousands in taxes, but they can also trigger Medicare IRMAA surcharges that quietly add up to more than $5,000 a year. Most retirees never see it coming, because the rules f...
Today, I'm thrilled to welcome Fritz Gilbert back for his second appearance on the podcast. Fritz is an award-winning blogger and author of The Retirement Manifesto, one of the most influential retire...
Jeremy Keil explores 7 money moves you can consider before the new year to lower your taxes and keep more of your money in retirement. Every December, people scramble to finish holiday shopping, trave...
In this episode, Roger Whitney, a retirement planner with 30 years of experience, breaks down annual gifting limits and year-end planning. He shares practical strategies for giving that make a real im...
Steve spent more than two decades building video games, working with a team that felt more like family than coworkers. By all measures, he loved his work. But a heart attack in 2021 changed everything...
Most retirement advice quietly assumes you have a partner: two incomes, two Social Security checks, someone to split expenses with, someone to catch the slack if something goes wrong. But for singles,...
Retiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this conversati...