Episode
The Top Retirement Questions You Should Be Asking (But Might Be Missing), Ep #203
- Podcast
- RETIREMENT MADE EASY
- Published
- Jan 31, 2026
- Duration seconds
- 2325
- Processing state
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Summary
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 meltdowns for those suffering from "2008 PTSD" and why we've decided to keep this podcast 100% ad-free and sponsor-free to maintain our integrity. Whether you are five years out from retirement or already there, this Q&A session is designed to help you stress-test your own plan against the questions you should be asking. You will want to hear this episode if you are interested in... (05:26) Can You Save "Too Much" for Retirement? (09:06) Social Security and Spousal Benefits. (12:41) Maximizing HSAs for the Long Term. (15:27) Handling the Long-Term Care Question. (16:47) The Best Withdrawal Strategies. (20:17) The Truth About Roth Conversions. (24:40) The Retire Strong Bucket Strategy. (27:19) Protecting Against Economic Meltdowns. (32:16) Do I Need a Trust? The Balance Between Saving and Living One of the first questions I tackled was, "Am I saving too much?". It sounds counterintuitive, but I believe the answer can be yes. If saving for retirement is impacting your current lifestyle to the point where you are putting off vacations or postponing joy, you might be overdoing it. While retirement is a priority, you have to live today, too. On the flip side, we discussed the "when can…