Are you actually prepared to navigate the complexities of retirement? We’re exploring Fritz Gilbert’s Six Lessons From Six Years of Retirement, shared from his blog The Retirement Manifesto.

One by one, we’ll walk through these lessons, keeping in mind that retirement is an evolving journey, not a static experience. For those who still need to optimize their post-work life, these lessons will show you a roadmap.

We then talk about a listener question about portfolio management—whether to prioritize Roth conversions or refilling cash buckets when your investments outperform expectations. We get deep into the importance of tax diversification and flexibility in retirement, especially why having options—whether it’s a Roth, brokerage, or IRA—is absolutely crucial when facing financial uncertainties.

If you’re preparing for or already navigating retirement, today is an excellent lesson from the ‘upperclassmen’—those a few years ahead of us in the retirement game.

• The Retirement Podcast Network
• Original Six Lessons article by Fritz Gilbert (and The Retirement Reality Series)
• Dan Sullivan’s The Strategic Coach program

• Fritz Gilbert’s The Retirement Manifesto

• Become a Client: www.retirementstartstoday.com/start
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• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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Retirement is not just a transition from work to leisure. It’s a continuous journey of self-discovery. We explore the story of Tom, who reflects on the emotional and financial challenges he faced after leaving a successful career. From adjusting to a fixed income to finding new ways to matter outside of his career, Tom’s experiences give us valuable lessons for those nearing retirement.

In light of Tom’s story, we talk more about Roth conversions and the evolving rules surrounding Required Minimum Distributions (RMDs). We’ll tell you how to manage Roth conversions, even after reaching RMD age, and the importance of tax planning as part of a truly comprehensive retirement strategy.

Learn how to make smarter financial decisions as you prepare for (or continue through your continuous journey of) retirement.

• [2:06] What challenges arise when going from a fulfilling career to retirement?
• [3:11] How do you cope when you’re no longer excited about retirement?
• [5:31] Can part-time work in retirement bring meaning or just fill time?
• [4:56] How do you adjust to losing status and income?
• [4:03] Why is adapting to a fixed income harder than expected in retirement?
• [9:46] How many Roth conversions can you make after turning 73?
• [10:41] Is converting IRA funds to a Roth still a good strategy after RMD age?
• [12:07] What happens if you delay your first Required Minimum Distribution (RMD)?
• [13:50] How do changes in tax laws impact retirement decisions?

• The Retirement Podcast Network
• Tom Pendergast’s Blog: Out Over My Skis (Retirement Freedom or Free Fall article)

• Tom Pendergast’s Blog

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

You know inflation is something to consider in retirement, but how much should you worry about it?

On this episode of Retirement Starts Today, we’ll explore an article from Of Dollar and Data that dives into the nitty gritty of inflation by analyzing three hypothetical retirement scenarios.

Learn how to plan for any eventuality so that you can better prepare for rising costs as you age.

• [2:02] How inflation impacts retirement
• [9:10] In conclusion
• [11:05] Do balanced funds make sense in the distribution stage of retirement?

• The Retirement Podcast Network
• Our Annual Listener Survey
• Of Dollar and Data

• Get the Retire-Ready Toolkit:http://retirementstartstodayradio.com/
• Follow Ben on Twitter:https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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In retirement, retirees make the big switch–drawing on savings rather than contributing to them. This is often when the trouble comes–the psychological hurdle comes when it’s time to start spending your hard-earned savings.

In this episode, you’ll learn how to understand the mental barrier that comes with the big switch and learn strategies to overcome it. Listen to learn how to use your retirement funds without guilt or fear of financial instability.

• [1:22] Will you need permission to spend in retirement?
• [4:06] Strategies to overcome your mental hurdle about spending
• [14:57] How do you handle the taxes from different types of income?

• The Retirement Podcast Network
• Annual Listener Survey
• Morning Star article

• Get the Retire-Ready Toolkit:http://retirementstartstodayradio.com/
• Follow Ben on Twitter:https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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Knowing when to retire is not just an economic decision; it’s highly personal. In an era where your work is with your identity, deciding when to retire can feel monumental. So how do you know when the time is right? That’s what we’ll explore in today’s episode.

In addition to discussing this retirement headline, Bret Mulvaney joins the show again to help me answer our listener question. Press play to listen.

• [1:06] Retirement Starts Today updates
• [3:48] How do you know it’s time to retire?
• [12:35] Does bank health matter if it is FDIC insured?

• The Retirement Podcast Network
• Vox article
• Dan Sullivan - The Strategic Coach

• Get the Retire-Ready Toolkit:http://retirementstartstodayradio.com/
• Follow Ben on Twitter:https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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Do you feel pain when spending money? Or perhaps it’s the opposite, and you spend a little too freely without much thought, pain, or remorse?

In this episode of Retirement Starts Today, we’ll explore an article on how to make the most out of retirement by trying to land somewhere in the middle of the spending spectrum. Whether you find yourself to be a “tightwad” or a “spendthrift” you’ll find this episode to be a helpful exploration of gaining happiness from your retirement spending plan.

• [1:22] The two types of money people
• [5:20] Pre-establish pivot points
• [11:45] How to deal with rising insurance premiums

• The Retirement Podcast Network
• The Wealth of Common Sense

• Get the Retire-Ready Toolkit:http://retirementstartstodayradio.com/
• Follow Ben on Twitter:https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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It’s easy to make mistakes in your investment portfolio, but as you get closer to retirement, it becomes more important than ever to make sure you are maximizing your financial health so that you can achieve your long-term goals.

In this episode of Retirement Starts Today, we’ll take a look at an article written by Christine Benz which highlights several common errors that investors make. Listen in to avoid these mistakes and learn the actions you can take to rectify the problems.

• [1:34] Are you making these common portfolio mistakes?
• [9:08] Does your asset allocation reflect your portfolio goals?
• [12:13] Amy is worried about staying invested, what can she do?

• The Retirement Podcast Network
• MorningStar article

• Get the Retire-Ready Toolkit:http://retirementstartstodayradio.com/
• Follow Ben on Twitter:https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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What would you say your retirement confidence level is? If you’re like many super-savers, it may be surprisingly low.

In this episode of Retirement Starts Today, we’ll explore an article from Investment News that dives into a phenomenon where wealthier Americans who are confident in their money management skills still feel shaky about retirement and transferring their wealth to their heirs.

Listen in to learn how to become more confident in your retirement plan and stick around for the listener question where we discuss just how safe annuities really are.

• [1:22] Why are supersavers not confident in their retirement plans?
• [4:18] How to become more confident in your retirement plan
• [7:56] How safe are annuities?

• The Retirement Podcast Network
• BOOK - Die with Zero by Bill Perkins
• Investment News article

• Get the Retire-Ready Toolkit:http://retirementstartstodayradio.com/
• Follow Ben on Twitter:https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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