Think You’re Ready to Retire? 10 Overlooked Signs You’re Not, Ep 191
Release Date: 07/15/2025
RETIREMENT MADE EASY
Today, in our 199th episode, I dive into some timely updates on Social Security and answered a batch of long-overdue listener questions. We kick things off with the newly announced 2.8% cost-of-living adjustment (COLA) for Social Security benefits starting January 2026. While that sounds like good news, I cautioned listeners not to celebrate too quickly. Medicare Part B premiums are expected to rise by 11.6%, or about $21.50 per month, which will eat into that COLA, leaving most recipients with a net increase of only around $34.50. I argue that announcing the Social Security COLA a month...
info_outlineRETIREMENT MADE EASY
In this episode of the Retirement Made Easy podcast, I delve into 401(k)s: how they work, why they matter, and how to maximize their benefits. I break down the basics in simple terms, just like I always aim to do, because retirement planning shouldn’t be confusing. I discuss the differences between good and not-so-great 401(k) plans, the pros and cons of keeping your money in a 401(k) versus rolling it into an IRA, and how changes in providers can impact your investment options. I also share a helpful government site for tracking down old retirement accounts and explain why Roth conversions...
info_outlineRETIREMENT MADE EASY
Are you confident your retirement plan covers everything, or are there blind spots that could cost you down the road? In this episode of the Retirement Made Easy podcast, I reveal six commonly overlooked areas that can quietly sabotage even the most well-intentioned retirement strategy. From inflation shocks and healthcare surprises to tax missteps and market overconfidence, I’ll walk you through the pitfalls I see time and again so you can learn how to avoid them. If you want a retirement that’s not just comfortable but resilient, this episode is a must-listen. My goal is to walk you...
info_outlineRETIREMENT MADE EASY
In this episode, I tackled some of the most common and pressing questions I’ve received from listeners, prospective clients, and current clients at . These questions are all centered around one big theme: preparing for retirement with clarity and confidence. Whether you're wondering about old 401(k)s, required minimum distributions (RMDs), or how to structure your retirement income, we covered a lot of ground. One of the first things I addressed was the new government resource for tracking down forgotten retirement accounts: . If you think you might have an old 401(k) or pension...
info_outlineRETIREMENT MADE EASY
Over the past few weeks, I’ve had several clients and prospective clients ask me the same question: “Should I keep my life insurance in retirement?” Life insurance is something we all tend to think of as essential when we’re younger (when we’ve got a mortgage, kids at home, maybe only one working spouse). But once you’re nearing or in retirement, things change. So, the question becomes: Does it still make sense to pay for life insurance? In many cases, the answer depends on your goals and financial picture. I’ve seen cases where people are paying big premiums for small death...
info_outlineRETIREMENT MADE EASY
Do 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...
info_outlineRETIREMENT MADE EASY
Are you confident your retirement plan is built to last-or could there be a trap door waiting to open beneath your feet? In this episode, I shine a light on the hidden dangers that can derail your retirement. Have you ever considered what would happen if your pension were suddenly cut in half? It has happened to retirees from major companies before, and it could happen again. I delve into real-life stories of people who thought they were financially secure, only to be blindsided by risks they hadn’t seen coming. From unexpected inflation spikes (like a 27% jump in homeowners insurance)...
info_outlineRETIREMENT MADE EASY
Retirement planning isn’t just about investments and Social Security; it’s also about how you budget and prepare for the expenses you know are coming. In this episode, I break down two essential but often misunderstood tools: sinking funds and target date funds. First, I explore how sinking funds, popularized by the likes of Dave Ramsey, can help retirees avoid high-interest debt and budget for large, irregular expenses like vacations, home improvements, or even a future wedding. I share personal examples and stories from my clients to show how setting aside money intentionally can be a...
info_outlineRETIREMENT MADE EASY
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...
info_outlineRETIREMENT MADE EASY
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...
info_outlineMany 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.
You will want to hear this episode if you are interested in...
- (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.
Resources & People Mentioned
- 3 Steps to Retirement Planning
- https://www.youtube.com/@RetirementMadeEasy
- https://retirestrongfa.com/resources
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
On Apple Podcasts, Spotify, Google Podcasts