In this episode of the Baird Retirement Management Show, we continue our series exploring Christine Benz's book How to Retire by focusing on her conversation with Mike Piper, CPA and author of the Oblivious Investor blog. Known for making complex financial topics simple and practical, Mike shares critical insights on how to approach tax planning before and throughout retirement. We cover: Why lifetime tax planning matters more than minimizing taxes year-by-year How to strategically use 401(k)s, IRAs, Roth accounts, HSAs, and taxable brokerage accounts The powerful but often overlooked role of HSAs in retirement and estate planning Why Roth conversions deserve careful, customized planning The best practices for sequencing withdrawals across account types to manage future tax bills How to maximize the benefits of Qualified Charitable Distributions (QCDs) starting at age 70½ Strategies for managing Social Security taxation and Medicare IRMAA surcharges The benefits of giving financial gifts to loved ones during your lifetime instead of through your estate Throughout the conversation, we highlight the balance between minimizing taxes today and avoiding bigger tax issues down the road—especially as new rules for inherited IRAs and RMDs change the retirement landscape. If you're preparing for retirement or helping clients navigate these decisions, this episode offers "terribly useful" advice you won't want to miss.

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