The Social Security Surprises That Could Cost You Thousands, Ep 190
Release Date: 06/30/2025
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...
info_outline
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...
info_outline
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. ...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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_outline
Avoiding Retirement Regrets: What Retirees Say They’d Do Differently Ep #206
RETIREMENT MADE EASY
On the show this week, I draw on real-world experiences from current retirees to uncover the surprises, challenges, and valuable lessons they wish they’d known before stepping into retirement. If you're curious about the realities of social interaction after leaving the workforce, managing rising healthcare costs, or navigating company-specific 401(k) features, this episode is for you. You will want to hear this episode if you are interested in... [00:00] Retirement lessons from retirees [08:23] Prioritizing tax planning in retirement [15:06] Retirement accounts &...
info_outline
Tax Planning Tactics and Life Insurance Questions, Ep #205
RETIREMENT MADE EASY
In today's show, I tackle two hot topics listeners have been asking about: tax planning in retirement and the role of life insurance in your golden years. Drawing from real questions and common scenarios. But that's not all: I also dig into the nuances of life insurance in retirement, explaining when it makes sense to keep or reconsider a policy, and how it can be a powerful tool for risk management, legacy planning, or supplementing income. You will want to hear this episode if you are interested in... 06:03 Tax planning vs. preparation 11:17 Optimizing Roth conversions in...
info_outlineMost people treat Social Security as a fixed outcome, just another box to check when retirement arrives. Select an age, complete the form, and proceed. But the truth is, your choices around Social Security can unlock, or quietly erase, tens of thousands of dollars over time.
The timing of your claim, whether you’re still working, your marital history, even how you coordinate with your spouse’s benefit… it all matters. And yet, plenty of financial advisors either avoid the topic or admit they don’t know how the system works. That leaves you on your own to navigate rules that weren’t designed to be intuitive, and change more often than most people realize.
We’re walking through the kinds of Social Security questions that don’t get answered anywhere else. From how remarriage changes your options, to what really happens when you claim while still working, to why your savings could shrink faster than expected, these aren’t niche hypotheticals. They’re decisions with long-term effects, and it’s time more people knew what’s really at stake.
You will want to hear this episode if you are interested in...
- (00:00) The Social Security Surprises That Could Cost You Thousands.
- (04:11) What your advisor might not know (but should) about Social Security.
- (06:25) The earnings test demystified through a real-life example.
- (09:39) Spousal, ex-spousal, and survivor benefits: who qualifies and when.
- (14:57) Major policy changes: The Fairness Act and unexpected lump sum payouts.
- (26:20) Legal custody, grandchildren, and overlooked Social Security benefits.
Resources & People Mentioned
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
Subscribe to Retirement Made Easy