Choosing the Best Month to Retire, Ep#216
RETIREMENT MADE EASY
Retirement is the beginning of a new story, and the decisions you make leading up to your last working day can significantly impact your financial well-being and peace of mind. On the show this week, I focus on the importance of timing your retirement and how choosing the specific month to retire can significantly impact your finances, taxes, and benefits. There are various financial and emotional factors to weigh—ranging from optimizing pensions and bonuses to health insurance coverage and even non-financial considerations like climate and seasonality. Careful planning avoids...
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Avoiding 3 Common Financial Pitfalls After You Stop Working, Ep #215
RETIREMENT MADE EASY
In this episode, I take you through the three most common mistakes people make in retirement—and how you can avoid them to set yourself up for long-term success. From overspending in the early days of retirement to overlooking crucial tax strategies and entering retirement without a written income plan, I discuss why these pitfalls happen and what you can do differently. Later in the episode, it’s rapid fire as I answer your listener questions on topics like Social Security benefits, Roth conversions, pension payout choices, and how to invest your retirement accounts once you leave the...
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How to Adjust Your Retirement Plan for Social Security Uncertainty, Ep #214
RETIREMENT MADE EASY
This week I’m discussing the latest Social Security Trustees Report, what it means for your future benefits, what changes may be coming, and how millions of Americans are already planning ahead. I’ll dig into the psychology and strategy of spending down your savings once you retire, including how to transition from saving to spending, why an “intentional adjustment” matters, and the critical role of having a written plan. I also answer listener questions about withdrawal strategies and how to weigh the decision of working “one more year.” You will want to hear this...
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The Overlooked Essentials of a Well-Prepared Retirement Plan, Ep #213
RETIREMENT MADE EASY
Retirement is often painted as a well-earned period of leisure, adventure, and relaxation. Yet, the journey to a fulfilling retirement is rarely straightforward. On this episode of the show, I’m shining a light on the intricate realities lying beneath common assumptions—and how the right planning, rooted in your personal goals and beliefs, makes all the difference. I also share an eye-opening case study highlighting the difference between being told you’re “good to retire” and actually being prepared for retirement. You will want to hear this episode if you are...
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Breaking Down Retirement Mind Blocks, Ep #212
RETIREMENT MADE EASY
The conversation this week explores the mindset shifts required as individuals move from years of saving and accumulating wealth to the daunting prospect of spending down those savings. Emotional readiness, habits, and even arbitrary financial goals can become barriers to making the leap into retirement—even when the numbers already add up. I share practical strategies for addressing these mental roadblocks, emphasizing the importance of holistic preparation: not just being financially set, but also feeling ready psychologically, emotionally, and spiritually for the next chapter. ...
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Avoiding Tax Traps: Selling Capital Gains and Managing Company Stock, Ep #211
RETIREMENT MADE EASY
Retirement planning is about more than just saving money—it’s about making smart decisions with your finances to ensure that you keep as much of what you’ve earned as possible. On the show this week, I’m sharing essential strategies for managing your taxes in retirement—including a real-life example of a couple selling $146,000 in capital gains and paying zero taxes. I break down the benefits of non-retirement brokerage accounts, clarify the rules around capital gains and losses, and reveal a key element of the tax code that hasn’t changed in nearly 50 years. In the second half of...
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Retiring Soon? What 2026’s Economic Landscape Means for Your Plans, Ep #210
RETIREMENT MADE EASY
What does it mean to retire in 2026, and how does today’s retirement landscape differ from 10 or 20 years ago? With more retirees facing challenges such as rising healthcare costs, higher cost of living, concerns about Social Security, shifting demographics, and the impacts of national debt, this episode digs into the current risks and opportunities for those planning their golden years. I share insights from a recent Goldman Sachs retirement study and answer listener questions on retirement planning software, investment strategy before retirement, handling 401(k) and IRA loans, and Social...
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Clearing Up Roth IRA Confusion, Ep #209
RETIREMENT MADE EASY
When it comes to retirement planning, understanding tax-advantaged accounts like Roth IRAs, knowing how to select a trusted advisor, and making optimal income choices are key building blocks for long-term financial confidence. On this episode of the Retirement Made Easy podcast, I’m digging into the details of Roth IRAs, Roth conversions, navigating advisor relationships, and the complex art of Social Security timing. With tax rules, income strategies, and advisor choices constantly evolving, continuous education and proactive planning are essential. If you’re part of the 80% of...
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Protect Your Retirement and Make Smarter Decisions in Uncertain Times, Ep #208
RETIREMENT MADE EASY
When markets feel unsettled, it can be hard not to worry. Headlines about war, inflation, falling retirement balances and political uncertainty can make even experienced investors feel uneasy. But as this episode of Retirement Made Easy highlights, volatility is not unusual — it is part of investing. The key is not to avoid every downturn. It is to respond in a way that supports your long-term retirement goals. From managing market dips to understanding survivor benefits, long-term care, and retirement income decisions, this episode covers some of the most important issues retirees...
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Demystifying HSAs, FSAs, and Social Security Benefits, Ep #207
RETIREMENT MADE EASY
Retirement planning can feel overwhelming, but understanding key benefits and strategies can help you make the most of your financial future. On the show this week, I tackle listener questions on Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), and Social Security. If you’re considering an HSA, are curious about contribution limits, or want to know how HSAs can work alongside FSAs, I break it down in simple, clear language. I also answer a wide range of Social Security questions, and discuss how your benefits are calculated, timing your claim, navigating survivor benefits,...
info_outlineDo you know if you’ll retire on time? In this episode, I explore a question I often hear: Why do some people retire on time, confidently, and on track, while others keep pushing it off or feel like it will never happen?
Additionally, I examine the differences in retirement experiences between men and women. Along the way, I share personal insights, stories from clients, research findings, and practical planning tips that can help you prepare for a retirement you truly enjoy.
I share a powerful study from Harvard Business School that really stuck with me. This study shows how important it is to not only think about your goals but to write them down and make a plan to achieve them.
When it comes to retirement, I always ask people to be as specific as possible, right down to the exact month or even day they want to retire. The more detailed you are, the more likely you are to hit those targets.
I also talk about how retirement often looks different for men and women. Women frequently take on caregiving roles and are more likely to need long-term care themselves, making healthcare planning especially important.
Men typically pay more for Medicare supplements, while life insurance tends to be cheaper for women. I’ve also noticed that women often prioritize legacy goals, while men usually have pricier hobbies. Understanding these patterns can help couples build a more balanced retirement plan.
Another important topic I cover is the common belief that expenses and taxes drop significantly in retirement. I don’t buy it. Healthcare costs, insurance premiums, and daily expenses like trash service, postage, and groceries keep going up.
Plus, inflation varies by location, so where you live matters a lot in your retirement plan. It’s important to factor in local cost-of-living differences because they can impact your budget quite a bit.
You will want to hear this episode if you are interested in...
- (00:00) Intro.
- (03:30) How a specific retirement plan shows if you’re on track.
- (06:30) Insights from a Harvard study on goal setting.
- (09:40) Differences in retirement planning for men and women.
- (17:20) Will expenses be cheaper in retirement?
- (24:00) our free resources to help your planning.
Resources & People Mentioned
- Value of 2013 dollars today | Inflation Calculator
- 3 Steps to Retirement Planning
- Why Some Retirement Products Can Trap Your Savings (and What to Watch For), Ep 187
- RetireStrong Financial Advisors | Financial Planner St Louis
Connect With Gregg Gonzalez
- Email at: Gregg.gonzalez@lpl.com
- Podcast: https://RetireStrongFA.com/Podcast
- Website: https://RetireStrongFA.com/
- Follow Gregg on LinkedIn
- Follow Gregg on Facebook
- Follow Gregg on YouTube
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