January 31, 2026

The Top Retirement Questions You Should Be Asking (But Might Be Missing), Ep #203

38 minutes

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 I retire?" question. I argue that a better question is "when do I want to retire?" because for many, work provides identity and purpose that shouldn't be discarded just because you hit a financial number.

The "Gas Guzzler" Portfolio: A Lesson in Tax Efficiency

We also dove into investment strategies that minimize tax burdens. I use the analogy of a vehicle: you might have a hybrid getting 50 miles to the gallon, or a massive truck getting 11 miles to the gallon. When your account is small, you might not notice the "fuel inefficiency" of high taxes, but as your portfolio grows, those inefficiencies magnify.

This ties directly into withdrawal strategies. I shared a story about someone who planned to drain their 401(k), then their brokerage, then their Roth, completely missing the boat on tax planning. You need a coordinated strategy to lower your lifetime tax bill, not just pay it as you go.

Planning for the "What Ifs"

Finally, we addressed the question, "Are we missing anything?". It's easy to plan for the monthly bills, but people often forget to factor in massive one-time expenses like weddings for their children or the fact that healthcare inflation historically outpaces standard inflation.

We also touched on the fear of another 2008-style crash. If you are losing sleep over a potential economic meltdown, it's a sign to re-evaluate your risk exposure. You might be willing to trade some potential high returns for the peace of mind that comes with a more conservative approach.

Resources & People Mentioned