Many people dream of retiring as soon as possible, but rarely stop to ask if they’re truly ready. It’s easy to assume you’ll figure things out when you get there, but this episode challenges that thinking by revealing 10 overlooked signs you may not be ready to retire yet. Even if you’re eager to leave the 9-to-5 behind, there are critical financial, emotional, and lifestyle factors you might not have fully considered, ones that can derail your dream if ignored.

We’ll explore issues like carrying too much debt, lacking a solid income plan, underestimating healthcare costs, or not having a clear picture of what you’ll actually do all day. For many, these topics can be uncomfortable because they reveal blind spots that feel hard to fix. But in walking through them one by one, we highlight how acknowledging these signs isn’t about delaying your freedom, it’s about ensuring you can sustain it joyfully and securely. You’ll discover practical ways to reduce financial risks, anticipate new expenses, and plan the life you actually want once work ends.

By the end of this episode, you’ll not only recognize the hidden gaps in your own plan but also see the value of taking action now. Whether that means rethinking your budget, getting strategic about Social Security, or simply having more honest conversations with your partner, you’ll leave with a clearer idea of how to transition from working years to retirement with confidence. Instead of winging it, you’ll be ready to retire on purpose, with eyes wide open.

• (00:00) Intro.
• (00:27) YouTube channel and free resources plug.
• (03:13) 10 signs overview and Sign 1: Carrying significant debt.
• (05:07) Sign 2: No retirement income plan.
• (06:17) Sign 3 and 4: Missing budget and healthcare costs.
• (09:43) Signs 5 - 7: Social Security, long-term care, RMD planning.
• (13:05) Signs 8 - 10: Emotional readiness, spousal coordination, investment repositioning.

• 3 Steps to Retirement Planning
• https://www.youtube.com/@RetirementMadeEasy
• https://retirestrongfa.com/resources
• https://retirementmadeeasypodcast.com

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
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Most 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.

• (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.

• 3 Steps to Retirement Planning
• https://www.retirestrongfa.com
• https://www.ssa.gov

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
• Follow Gregg on LinkedIn
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Most people nearing retirement aren’t thinking about tax legislation; they’re focused on their savings, Social Security timing, or making sure their lifestyle doesn’t outlive their money. But what if a single bill quietly reshapes the rules you’ve been planning around? In this episode, I break down a new piece of legislation that’s generating significant political buzz but concealing some far-reaching implications for retirees and pre-retirees alike. If you’ve heard soundbites about “the biggest tax cut in history,” you might assume you’re in for a windfall. The truth? It’s a lot more nuanced and more temporary than headlines let on.

I walk you through what’s actually in the bill, what got stripped out (spoiler: Social Security tax relief didn’t make the cut), and how all this might hit people aged 55 to 70. Then, in classic Retirement Made Easy fashion, I pivot to listener questions on how to tap your accounts in the smartest order, why RMD math isn’t as harsh as people think, and whether borrowing against your house in a downturn is ever a good idea. I close with a sobering but motivating list of what can go wrong in retirement planning and how to think more clearly and conservatively about your future.

• (00:00) Intro
• (04:19) Key changes in the bill that might affect retirees
• (13:08) Listener Q1: Which retirement accounts to tap first?
• (19:58) Listener Q2: Clearing up RMD confusion
• (23:03) Listener Q3: Is using home equity a good backup plan?
• (27:06) Listener Q4: What could blow up your retirement plan?

• 3 Steps to Retirement Planning
• https://www.retirestrongfa.com
• “The One, Big, Beautiful Bill…” https://www.whitehouse.gov/articles/2025/05/one-big-beautiful-bill-is-a-once-in-a-generation-chance/
• IRS RMD table https://www.irs.gov/retirement-plans/plan-participant-employee/retirement-topics-required-minimum-distributions-rmds

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
• Follow Gregg on LinkedIn
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Most people heading into retirement think they’ve got it covered: a pension, some savings, maybe Social Security. But what if the things they’re counting on are either misunderstood or dangerously overestimated? This episode sheds light on a few hard-hitting truths that most folks never hear until it’s too late. Retirement income isn’t just about how much you have, it’s about how that income behaves over time, and how taxes, inflation, and planning gaps quietly erode the security you thought you had.

As I walk through the mechanics of Social Security, from its inflation adjustments to its unique tax advantages, you’ll begin to see why it’s not just another income stream. It’s one of the only sources designed to rise with the cost of living. Contrast that with private pensions, which often never grow a penny, and you’ve got a ticking time bomb if you’re relying too heavily on the wrong source. And then there’s the planning itself: too many households have just one person steering the ship. That “key man risk” can leave the entire plan vulnerable.

Whether you’re married, single, or retired, this episode pushes you to ask the uncomfortable but necessary questions: Who’s my co-pilot? Am I building a plan around stable, tax-smart income? And have I surrounded myself with people who will actually support the goals I’ve set? Because retirement isn’t just about having a plan, it’s about having the right one, built on the right truths.

• (00:00) The overlooked truths about your retirement.
• (01:30) Social Security as the foundation of most people's retirement income.
• (03:00) What most people miss about Social Security’s inflation adjustments.
• (06:00) Why Social Security's tax treatment beats other income sources.
• (08:59) The overlooked downside of fixed pensions in a rising-cost world.
• (14:25) The real risk of planning retirement without a financial “co-pilot.”
• (19:10) Why you should only share retirement goals with supportive people.

• 3 Steps to Retirement Planning
• https://www.ssa.gov
• https://www.irs.gov/retirement-plans/roth-iras 

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
• Follow Gregg on LinkedIn
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Most people who are gearing up for retirement are heads-down focused on building savings. But there’s one important thing they don’t consider: what happens to your money once it’s “locked away” in certain retirement products. In this episode, Gregg Gonzalez digs into annuities - what they are, why they’re sometimes pitched so hard, and how they can quietly trap your savings if you're not careful. If you’re just assuming a big 401(k) or IRA balance will mean total freedom in retirement, it’s time for a closer look.

He breaks down the four types of annuities, the fine print you need to watch for, and the difference between a tool that fits your goals and one that could slow you down. He shares real-world examples of how well-meaning people end up in bad products, and why working with someone who’s truly on your side (not just selling something) can make all the difference.

By the end, you’ll not only be able to spot the traps, you’ll know exactly what questions to ask, what options to consider, and how to move forward with a retirement strategy that matches your life, not just a sales pitch.

• (00:00) Why some retirement products can trap your savings.
• (03:24) Announcement of upcoming Social Security seminars and webinar idea.
• (05:24) Setting up today’s focus: common misconceptions about annuities.
• (6:00) Breakdown of the 4 main types of annuities and when they might fit.
• (19:20) Listener Q&A: Social Security spousal benefits and retirement savings questions.
• (31:30) Closing thoughts on aligning retirement goals with financial behavior.

• 3 Steps to Retirement Planning
• Fidelity Retirement Savings Study

• Email at: [email protected]
• Podcast: https://RetireStrongFA.com/Podcast
• Website: https://RetireStrongFA.com
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Retirement doesn’t come with a universal playbook, but you can learn a lot from people who’ve already been through it. Gregg shares stories from real clients that reveal what quietly sets the most successful retirees apart. These aren’t surface-level tips, they’re patterns that show up again and again in the lives of people who’ve built the kind of retirement others only hope for.

The episode highlights three strategies that create a strong foundation: keeping cash accessible for both the unexpected and the inevitable, setting personal goals that matter to you (not just sound impressive), and staying regularly engaged with your financial picture over time. Together, they foster a sense of stability, clarity, and confidence that goes way beyond the numbers.

• (00:00) Why retirement advice needs real stories.
• (05:10) Why your emergency fund isn't enough.
• (10:40) The power of specific retirement goals.
• (15:00) Staying financially engaged without obsessing.
• (16:40) Social Security clawbacks & tax law shifts.

• 3 Steps to Retirement Planning
• Social Security Trustees Report

• Email at: [email protected]
• Podcast: https://RetireStrongFA.com/Podcast
• Website: https://RetireStrongFA.com
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You may believe your retirement is all set, with savings secured and timelines mapped out, but then the questions start flooding in, shaking that sense of certainty. This episode reveals the questions people start asking as retirement gets closer, from Roth conversions and Social Security to how inherited money works..

Gregg walks through questions from listeners and clients that reveal the lesser-known stuff, like why turning 73 or 75 matters way more than you’d expect, what changes if you’re still working, or how one checkbox on a beneficiary form can shift who ends up with your money. There’s also a closer look at long-term care insurance and why the math on it surprises most people.

This episode will make you stop and rethink your assumptions so that it doesn’t cost you dearly in the future.

• (0:00) The real retirement questions you should ask sooner rather than later.
• (03:45) Listener question #1 - Roth conversions and the five-year rule.
• (05:04) Listener question #2 - Roth IRA vs. Roth 401(k) contribution limits.
• (07:44) Listener question #3 - Beneficiary designations: pro rata vs. per stirpes.
• (10:38) Listener question #4 - Social Security growth after full retirement age.
• (14:37) Listener question #5 - What if Social Security income becomes tax-free?
• (14:41) Listener question #6 - Required minimum distributions and age updates.
• (19:28) Listener question #7 - Why long-term care insurance costs as much as it does.
• (24:18) Listener question #8 - When retirement income and market dips collide.

• 3 Steps to Retirement Planning
• Ed Slott - America’s IRA Experts - https://irahelp.com/

• Email at: [email protected]
• Podcast: https://RetireStrongFA.com/Podcast
• Website: https://RetireStrongFA.com
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Retirees usually think the tax decisions are done once they stop working. But the truth is, many are sitting on large pre-tax balances that can quietly lead to bigger tax bills later—especially when required minimum distributions kick in or a spouse passes away. It's not just about saving money, it's about how that money is taxed when you actually need to use it.

Roth conversions offer a way to shift those tax liabilities earlier, on your terms. I explain when that tradeoff makes sense and when it doesn’t, using clear, real-world examples. You’ll hear how a couple with zero current tax liability converted money without paying a dime, and why converting in a year with lower income or a temporarily down market might open the door to big savings. I’ll also break down why legacy plans, filing status changes, and Social Security taxation are key pieces of the puzzle.

• (0:00) The ins & outs of Roth conversions
• (1:55) The three tax buckets that shape retirement
• (6:32) When conversions are a no-brainer (and when they’re not)
• (9:54) How your tax bracket—and filing status—change the math
• (17:05) Roths as a better inheritance for your kids
• (24:57) Clearing up common Roth misconceptions

• 3 Steps to Retirement Planning

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
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Most people don’t think about market swings until their retirement accounts take a hit. If your 401(k) balance is dropping or you’re feeling uneasy, you’re not alone. Recent shifts, fueled by tariff changes and global uncertainty, have left many wondering what to do next. But you don’t have to ride this out blindly.

We break down why this is happening, how it impacts your savings, and what you can do to stay on track. Some investors take on more risk than they realize, and waiting too long to adjust can cost them. Knowing how to match your investments with your comfort level can make all the difference.

By the end, you’ll have a clearer picture of what’s happening, how past downturns compare, and ways to protect your retirement without panic moves. Because the best way forward is always preparation—not fear.

• (0:00) Why retirement savings feel unstable
• (6:40) Listeners’ concerns about retirement savings
• (9:30) The risk of being too aggressive with investments
• (11:40) The danger of over-concentration in a single stock
• (13:30) Social Security misunderstandings and key takeaways

• 3 Steps to Retirement Planning
• Visit Yahoo Finance to explore past market trends

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
• Follow Gregg on LinkedIn
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Most people heading into retirement focus on the numbers—savings, pensions, Social Security, and investments. But the biggest risk isn’t always financial. The way you think about retirement can shape your entire experience, and too often, blind spots get in the way of a smooth transition. Conversations with pre-retirees show just how much mindset influences confidence, decision-making, and even long-term security.

Common concerns like running out of money, healthcare costs, and inflation are valid, but they’re not always the biggest threats. Shifting focus can reveal risks that were never even on the radar. With the right adjustments, retirement can feel less like a leap into the unknown and more like a plan coming together. Plus, some important listener questions get answered, covering pensions, taxes, and financial planning decisions that can make all the difference.

• 3 Steps to Retirement Planning
• Pension Benefit Guaranty Corporation (PBGC) Information – pbgc.gov

• Email at: [email protected]
• Podcast: https://RetirementMadeEasyPodcast.com
• Website: https://StLouisFinancialAdvisor.com
• Follow Gregg on LinkedIn
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Subscribe to Retirement Made EasyOn Apple Podcasts, Spotify, Google Podcasts