Planning for Retirement with Kevin Lao

Kevin Lao
  • 4.9 (28)
  • INVESTING
  • UPDATED BIWEEKLY

After more than 17 years serving retirees, I’ve seen the same pattern: people spend 30–40 years building wealth, but the biggest financial decisions happen right before and after retirement. I’m Kevin Lao, a fiduciary financial advisor specializing in retirement income planning, Roth conversions, Social Security, tax strategies, RMDs, and smart investing for those with $1M+ saved. If you’re within 10 years of retirement or already retired and want clarity, confidence, and tax-efficient income, this podcast is for you. Bonus points if you love golf!

  1. MAR 24

    121: 5 Tax Planning Strategies When You’re High Net Worth, but Poor on Paper

    After you retire, you might find your net worth continuing to grow, but your 'taxable income' drops significantly. That can create major tax planning opportunities. Hence, 'High net worth, poor on paper.' I’ll explain how that period of time can open thedoor to smarter planning around ACA subsidies, Roth conversions, Social Security taxation, and 0% capital gains harvesting. Remember, these strategies should not be looked at in asilo. A move that helps in one area can easily impact another if it isn’t coordinated with your full retirement plan. What you’ll learn in this episode: What “high net worth, poor on paper” actually means Why low-income years in retirement can be powerful planning years How ACA premium tax credits work for early retirees The tradeoff between ACA subsidies and Roth conversions How the Roth conversion window can reduce future RMD problems How Social Security taxation can potentially be reduced with proper timing When 0% capital gains harvesting may make sense Why these strategies must be coordinated, not implemented one by one Why retirement tax planning is about timing taxes wisely, not just avoiding them If you want help building a retirement plan thatcoordinates investments, taxes, income, and leaving a legacy, you can learnmore at www.imaginefinancialsecurity.com Or, start with requesting a Mutual Fit Meeting by filling out this shortquestionnaire: https://form.jotform.com/250847998463173   Resources / related episodes:ACA Tax Credits:  The Cliff is Back in 2026:  https://youtu.be/iZcF5IuH1Bg?si=x5l4SnH2nl3wnYS1 $3m Net Worth, Free Healthcare(case study): https://youtu.be/iZcF5IuH1Bg?si=x5l4SnH2nl3wnYS1 Aggressive Conversions to makeSocial Security Tax Free: https://youtu.be/oeo3jT5iUbQ If you enjoyed this episode Please leave a 5-star review, follow the show, and shareit with someone who is close to retirement or recently retired. Thank you! -Kevin

    44 min

  2. MAR 17

    120: 5 Retirement Strategies to Protect Your Portfolio During the Iran Oil Crisis

    Are you retiring soon or recently retired and worried about market volatility, sequence of returns risk, and what the Iran conflict could mean for your plans? In this episode, I'm diving into what retirees should be considering as we head into potential prolonged volatility. I'll discuss the short term market impact of the conflict. Then, I'll touch on what I think might be an underlying long-term goal for the US getting involved. And most importantly, we'll touch on 5 strategies to help you prepare for and execute a successful retirement, despite this new wave of uncertainty. I hope it helps! -Kevin Request A “Mutual Fit Meeting” here ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multipleseven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place. ***This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    35 min

  3. MAR 10

    119: Social Security for Married Couples: The Survivor Benefit Mistake

    If you're married, your Social Security claiming strategy is not just about your benefit — it's about protecting your spouse’s income for life. In this video, I'll explain the most overlooked Social Security rule for married couples and how it can dramatically affect the surviving spouse’s financial security. Many retirees don’t realize that when one spouse passes away, one Social Security check disappears. The surviving spouse only keeps the larger of the two benefits, which means the higher earner’s claiming decision may be the most important Social Security decision you make. Using a real-life style example, Kevin walks through how delaying Social Security can significantly increase the survivor benefit, potentially adding thousands of dollars per month for the spouse who lives the longest. He also explains why couples who claim too early may unintentionally reduce the surviving spouse’s income during the most financially vulnerable years of retirement. However, this strategy doesn’t apply to everyone. I'll also share three situations where it may actually make sense to ignore the typical advice to delay Social Security, including health considerations, investment strategies, and withdrawal rate concerns. If you are within 5–10 years of retirement, married, and have saved $1M or more, this Social Security strategy could have a major impact on your long-term retirement income plan. ⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place. This is for general education purposes only and should not be considered as tax, legal or investment advice.

    8 min

  4. MAR 3

    118: Should You Annuitize in Retirement? 4 Surprising Benefits

    Are annuities really that bad? I’ve spent most of my career skeptical of annuities.  Especially the expensive, complicatedproducts often sold to retirees. I don’t sell annuities. I don’t earn commissions from them. And in most cases, I still am skeptical of how they are ‘sold’and not planned for. In this episode, I break down four surprising benefits ofannuitizing part of your fixed income, especially if you’re approaching retirement with $1M+ saved and want a smarter retirement income strategy. We’ll cover: • Why everyone is a bull… until the market drops 10% • How annuitization can reduce sequence of returns risk • Why payout rates (like 6%–8%+) is hard to replicate with a ‘safe withdrawalrate’ • How annuities can actually improve legacy outcomes in certain scenarios • The math behind lowering withdrawal pressure on your equity portfolio • How to evaluate TIAA Traditional payout options and vintages Retirement isn’t just about asset allocation. It’s about income design. And if you’re over 55, retiring soon, or already retired,understanding annuitization could materially impact your retirement income,stress level, and long-term legacy. Hope you find this useful. -Kevin ⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multipleseven figures), love golf and travel, and you want to make work optional whileminimizing taxes… welcome to the right place.   This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    14 min

  5. FEB 24

    117: TIAA Traditional Explained: How Much to Keep, When to Use It, and What to Do at Retirement

    If you’re a TIAA participant, there’s a good chance you own TIAA Traditional—and it may be one of the most misunderstood “investments” in retirement plans. In this episode, I’m breaking down TIAA Traditional, TIAA Real Estate and answering the biggest questions I hear from TIAA participants: ✅ Should I own TIAA Traditional? ✅ If so, how much should I keep there? ✅ Should I use the TIAA Real Estate Account? ✅ What should I do with TIAA Traditional after I retire? ✅ Bonus: How do I compare to other retirement savers? We’ll talk about the real issue most people miss—liquidity and contract type—and how TIAA Traditional can be used as a bond alternative or even as a retirement income floor depending on your plan. Resources mentioned: TIAA Real Estate Account Video, How to get money OUT of TIAA (contract breakdown) Video, Retirement Savings Relative to Peers ⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place. 💬 Comment Below What is your biggest TIAA question!?   This is for general education purposes only and should not be considered as tax, legal or investment advice.

    22 min

  6. FEB 17

    116: Are You Stuck in “One More Year Syndrome”?

    Lately, I’ve been seeing a TON of retirement planning content telling people: "Don’t work another year. Retire now. You’re wasting time." And honestly… as a retirement-focused financial planner, that message kind of rubs me the wrong way. Not because it’s always wrong… but because I think there’s an angle behind it. In today’s episode, we break down what One More Year Syndrome really is, why it’s become such a popular retirement planning trend on YouTube and podcasts, and why you may want to take this advice seriously… but also why you might need to take it with a grain of salt. Because retirement isn’t just about sitting on the beach 7 days a week. Retirement should be about purpose, meaning, freedom, and using your time, talents, and treasure in the way that matters most. I also share a powerful story from a recent conversation with a prospective client who reached out after losing three of his closest friends last year, and how that kind of wake-up call can completely change the way you think about retirement timing. At the end of this episode, I give you 3 questions to ask yourself to determine whether you’re truly delaying retirement for financial reasons… or if you’re simply afraid of stepping into the unknown. If you're in your 50s or early 60s, have saved $1M+ for retirement, and you're wondering whether you should retire now or work longer, this episode is for you. ✅ Questions Covered In This Episode: Should I retire now or work one more year?Is One More Year Syndrome real?How do I know if I’m financially ready to retire?How do I find purpose after retirement?What if I retire too early?What if I wait too long and regret it? ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place. 💬 Comment Below: Are you stuck in “one more year syndrome”? What’s holding you back from retiring today — taxes, market uncertainty, healthcare, or fear of the unknown? I’d love to hear from real retirees and pre-retirees. Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Connect with me here: ​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Join My Company Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ This is for general education purposes only and should not be considered as tax, legal or investment advice.

    15 min

  7. FEB 10

    115: “The 40-Year Retirement Test: Why the 4% Rule Might Be Making You Work Too Long”

    Is the 4% rule actually causing people to work 5 to 10 years longer than they need to? In this episode of The Planning for Retirement Podcast, Kevin Lao breaks down a series of real historical 40 year retirement backtests using withdrawal rates of 4%, 5%, 6%, and even 7%, and the results are shocking. Using Portfolio Visualizer, Kevin tests how different withdrawal rates would have performed starting in 1986 through 2025, and then compares those results to what happens when you retire into a tougher market environment like the lost decade (starting in 2000). This episode is all about the real retirement planning lesson most people miss: 👉 The market you retire into matters more than the rule you follow. And having a flexible withdrawal strategy beats blindly following any one “safe withdrawal rate.” In this episode, you’ll learn: • Why the 4% rule was never meant to be personalized • How a higher withdrawal rate can work in some retirement scenarios • Why sequence of returns risk can destroy even a “safe” retirement plan • How Social Security timing can reduce long-term portfolio risk • Why spending often declines in retirement (go-go, slow-go, no-go years) • How taxes and account types (taxable vs IRA vs Roth) impact retirement withdrawals • Why guardrails and flexible income planning are the key to retiring confidently If you're approaching retirement and trying to determine your safe withdrawal rate, this episode will help you understand what really matters, and why retirement planning isn’t about following one rule of thumb, it’s about building a plan that adapts. Resources: Guardrails, 4 Decision Rules Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Connect with me here: ​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Join My Company Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ This is for general education purposes only and should not be considered as tax, legal or investment advice.

    24 min

  8. FEB 3

    114: Retirement Planning If You Live to 100: 5 Moves You Can't Ignore

    What if you live to be 100 years old? A lot of retirement plans assume your portfolio needs to last 15–25 years… maybe 30 if you’re being conservative. But if you retire at 60 (or earlier) and live to 100, that’s a 40-year time horizon in retirement — and it changes everything. In this episode, I walk through five retirement planning considerations to address longevity risk for retirees in 2026 and beyond, including: • How to build paychecks in retirement (not just a portfolio) • Why getting too conservative can quietly increase risk over a long retirement • How to think about Social Security, pensions, and annuities as guaranteed income tools • Why long-term care planning is a logistics problem (that can become a money problem) • Spending phases: go-go, slow-go, no-go • And a legacy concept I love: giving with a warm hand instead of a cold one 📌 Free resource: I’m including a PDF in the show notes on the Guyton-Klinger “guardrails” decision rules (inflation rule, prosperity rule, portfolio rescue rule, portfolio management rule). Guyton and Klinger Decision Rules 👍 If this was helpful, subscribe and leave a 5-star review on Spotify/Apple Podcasts — it helps us reach and impact more people. Kevin Lao Links: Guyton and Klinger Decision Rules ⁠⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Connect with me here: ​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Join My Company Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ This is for general education purposes only and should not be considered as tax, legal or investment advice.

    31 min
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About

After more than 17 years serving retirees, I’ve seen the same pattern: people spend 30–40 years building wealth, but the biggest financial decisions happen right before and after retirement. I’m Kevin Lao, a fiduciary financial advisor specializing in retirement income planning, Roth conversions, Social Security, tax strategies, RMDs, and smart investing for those with $1M+ saved. If you’re within 10 years of retirement or already retired and want clarity, confidence, and tax-efficient income, this podcast is for you. Bonus points if you love golf!

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