The Ultimate 401(k) Guide Planning, Pitfalls, and Power Moves, Ep 198
Release Date: 11/01/2025
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_outlineRETIREMENT 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_outlineRETIREMENT 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_outlineRETIREMENT MADE EASY
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 ...
info_outlineRETIREMENT MADE EASY
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...
info_outlineRETIREMENT MADE EASY
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...
info_outlineRETIREMENT MADE EASY
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...
info_outlineRETIREMENT MADE EASY
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...
info_outlineRETIREMENT 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_outlineIn 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 might be worth considering. My goal is to help you take control of your financial future with clarity and confidence.
You will want to hear this episode if you are interested in....
- (00:00) Intro.
- (00:27) Overview of 401(k) Plans.
- (01:40) Resources and Services Offered.
- (02:48) Deep Dive into 401(k) Plans.
- (05:13) 401(k) Rollovers and Conversions.
- (10:53) Employer Contributions and Vesting.
- (19:52) 401(k) Loans and Company Stock.
- (22:58) Mega Backdoor Roth and Final Tips.
Smart 401(k) Moves: What to Know About Matching, Vesting, and Rollovers
I will explain how Roth conversions can be done while you're still working or after retirement, depending on your 401(k) plan’s rules. Not all plans allow them, and some require a hefty 20% tax withholding, which could be a drawback. I also break down how employer matching works (some companies offer generous matches, others offer none, and vesting schedules determine how much of that match you actually get to keep).
I stress the importance of checking your vesting status before leaving a job. Then I dive into profit-sharing, which can be even more valuable than matching, but it’s never guaranteed. I clarify a common misconception: rolling over funds from an old 401(k) or IRA into your current 401(k) won’t earn you a match. Finally, I talk about the pros and cons of rolling old 401(k)s into either your current plan or a rollover IRA. Personally, I favor rollover IRAs for their flexibility, investment freedom, and ease of Roth conversions.
Unlocking 401(k) Opportunities and Avoiding Pitfalls
I caution listeners about 401(k) loans. If you retire or get laid off, that loan must be repaid quickly, or it becomes taxable. Once you leave your employer, you can’t take out new loans from your 401(k) or IRA. I also touch on company stock in your 401(k); if you have a large concentration, talk to your financial planner about a tax strategy called net unrealized appreciation (NUA), which could work in your favor. Additionally, I introduce the “mega backdoor Roth,” another beneficial strategy that allows high earners to contribute beyond the standard limits if their plan permits it (up to $70,000 annually). Not all plans allow this, but it’s worth asking.
I also share my frustration that there’s no standardized way to compare 401(k) plans across companies. The best thing you can do is request your plan summary document and review it with a fiduciary advisor. Lastly, I offer a tip: some employers let you use unused vacation or PTO payouts as 401(k) contributions, which could help reduce your tax bill. It’s a smart move to look into before you retire.
Resources & People Mentioned
- 3 Steps to Retirement Planning
- FIVE 401(k) Secrets You Must Know
- Retirement Savings Lost and Found Database | Employee Benefits Security Administration
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