Think You’re Ready to Retire? 10 Overlooked Signs You’re Not, Ep 191
Release Date: 07/15/2025
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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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,...
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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 &...
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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...
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Retirement planning isn’t just about crunching numbers and sticking to a tight budget—it’s about envisioning what’s truly possible for your future. These hypothetical scenarios, often overlooked by retirees, can do more than just safeguard your financial well-being; they can enhance your happiness and help you discover opportunities you never thought attainable. You will want to hear this episode if you are interested in... 05:16 Encouraging Big Thinking in Retirement 10:15 Planning for Early or Delayed Retirement 11:50 Philanthropy and Charitable Giving in Retirement ...
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In this episode, I decided to do something a little different. Over the last two weeks, my team and I compiled a list of questions submitted by listeners and clients, some common, some obscure, and some that people simply don't know how to ask. I’ve got a legal pad in front of me with over 30 questions, ranging from "Am I saving too much?" to "Do I really need a trust?". We cover a lot of ground today, including the nuances of Roth conversions, the often-overlooked power of HSAs, and the "gas guzzler" analogy I use to explain tax-inefficient investing. I also address the fear of economic...
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Welcome to 2026! A new year brings a fresh set of rules for your retirement savings, and not all of them are straightforward. With the turning of the calendar comes changes to contribution limits, Social Security adjustments, and new tax mandates that could catch you off guard if you aren't paying attention. In this first episode of the year, I break down exactly what is changing for 2026, from the "good news" of higher contribution limits to the "bad news" of Medicare premium hikes that might eat up your entire Social Security cost-of-living adjustment. I also dive into a controversial new...
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How do you take the savings you’ve built over a lifetime and turn it into reliable income you can count on year after year? That’s a question I’ve been hearing more and more, and it makes sense, without a clear withdrawal strategy, retirees can unintentionally drain their accounts too quickly, trigger unnecessary taxes, or simply feel unsure about whether they’re doing things the right way. Making the shift from accumulating money to actually using it can feel uncomfortable, and my goal is to help people approach that transition with clarity and confidence. In this episode, I break the...
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In this 200th episode, I focus on the real pain points retirees face and the importance of planning ahead. Drawing from years of conversations with clients and listeners, today's discussion highlights how assumptions about retirement often don’t match reality, especially when it comes to taxes, lifestyle choices, and healthcare. Taxes remain one of the biggest surprises, as many retirees discover they’re not in a lower bracket after all. Withdrawals from 401ks, IRAs, and pensions are taxed as ordinary income, and Social Security can also be partially taxable. At the same time, couples must...
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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_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
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