Retirement SimpliFied with Eric Sigdestad CFP®

About Retirement SimpliFied with Eric Sigdestad CFP®

Retirement planning made simple. Every episode takes one real decision, pulled from an actual client conversation, and walks you through it in plain English: retirement withdrawals, Roth conversions, taxes, Medicare, Social Security, required minimum distributions, and more. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, with more than 10,000 client conversations about retirement behind me. Whether you're nearing retirement, already in it, or helping a parent through it, this show is for you. Subscribe on your favorite podcast app for a new episode every week and find us at https://RetireMeASAP.com. Produced by Eric Sigdestad, an investment adviser representative of SimpliFi, Inc., an SEC-registered investment adviser. Educational only, not individualized investment, tax, or legal advice; no advisory relationship. Client examples are anonymized, not testimonials. Consult a professional. www.adviserinfo.sec.gov

Publisher

Eric Sigdestad

Category

business · education

Language

en

Explicit

No

First episode

21 Jul 2026

Latest episode

19 Oct 2026

Latest episodes

16 episodes in the feed.

1. 

   19 Oct 2026

   Retiring at 62? The Three Years Before Medicare Cost More Than You Think

   Retiring at 62 leaves you with three years of health insurance to pay for before Medicare kicks in, and for a lot of people it's the biggest expense that never made it into their plan. In this episode, I walk through four ways to bridge that gap, the one number that decides what you'll pay, and why the bill can follow you well past 65. Watch this before you pick your retirement date. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. IRMAA - Why One Withdrawal Can Raise Medicare Costs Later: https://youtu.be/ClkV9Di7SE4 QCD's - Give the Exact Same Amount to Charity Without the Tax Bill: https://www.youtube.com/watch?v=CfwX909qnlk&t=1s ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here.

2. 

   12 Oct 2026

   Most Retirees Are Taking More Risk Than They Realize

   The decade around your retirement date is when your investment risk matters most, and most people go through it holding a mix set for a life they lived years ago. In this episode, I walk through 4 ways retirees end up carrying more risk than they realize, plus a hypothetical example where the timing of just two bad years leaves one retiree hundreds of thousands of dollars behind. Stick around for a 3-step homework assignment you can finish this week. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. Any tax-savings figures shown are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. All investing involves risk, including possible loss of principal.

3. 

   5 Oct 2026

   Give the Exact Same Amount to Charity Without the Tax Bill

   If you give to charity every year, you could be handing thousands of dollars to the IRS that you never had to pay. The charity gets every dollar either way, and the difference comes down to one choice most givers over 70½ never think to make. In this episode, I walk through a hypothetical example and the five mistakes that can wipe out the savings, including one that can cost you the entire benefit. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. The projected tax-savings figures shown in this episode are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. Individual results depend on your tax bracket, RMD amount, and gift size. All investing involves risk, including possible loss of principal.

4. 

   28 Sept 2026

   Don't Make Your 'Responsible' Kid the Only Heir

   Leaving everything to your "responsible" kid and asking them to look after their sibling feels like the choice that holds your family together, yet it can end up costing that child more than you'd ever expect. In this episode, I walk through a hypothetical $1,000,000 IRA left to one child, the two costs that come with that plan, and the one change that gets you what you wanted in the first place. If you have one child who has it together and one who doesn't, watch this before you update your beneficiary forms. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here.

5. 

   21 Sept 2026

   The Roth Conversion Golden Years

   Somewhere in retirement, there's a stretch of years when your income drops, maybe to the lowest point of your adult life, and nobody sends you a notice when it opens or when it closes. While it's open, moving money out of your IRA can cost you less than it ever will again. In this episode, I show you the three events that set your window, how to count the years you actually have, and the four ceilings that decide how much you can put through it before a conversion starts costing more than it saves. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- Timestamps: 0:00 There Is No Right Age 0:42 How a Roth Conversion Works 1:04 What Opens and Closes the Window 2:37 Counting Your Years 3:44 Three Reasons to Bother 4:56 The Four Ceilings 7:24 A Hypothetical: Jack and Diane, $1.8 Million 9:31 The Catch: You Can't Undo It 9:47 Three Questions Before You Convert 10:29 Bottom Line ------------------------------- This content does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. The figures and example shown are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. All investing involves risk, including possible loss of principal.

6. 

   14 Sept 2026

   RMDs Are Not The Monster You Think They Are

   The RMD warning you've heard for years is running on rules Congress rewrote five separate times since 2019, and the warning never caught up. Every one of those five changes worked in your favor, except for one group of retirees, where the same changes raised the stakes. In this episode, I show you exactly which side of that line you land on. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary — please consult with your adviser before acting on any information discussed here.

7. 

   7 Sept 2026

   The Real Cost of Pulling $25,000 Out of Your IRA This Year

   Ask five people what a $25,000 IRA withdrawal costs in taxes and you will get five different answers. In this episode, I do the actual math. I explain how the income tax staircase works, and why your tax bracket is a poor stand-in for what a withdrawal really costs. Then I show you the one number to pull off your tax return before you request a dollar, and I compare the two ways people get $25,000 into their checking account. Same money in your pocket, meaningfully different outcomes by the end of the year. If you are planning a withdrawal this year, for a new roof, a trip, or anything else, watch this before you fill out the form. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary — please consult with your adviser before acting on any information discussed here.

8. 

   31 Aug 2026

   The One Test That Answers "How Much Do I Need in Retirement?"

   Ask most people what they spend each month, and you get a confident answer. Ask them to prove it, and the number comes apart, spread across three or four credit cards, a checking account, and a couple of recurring charges nobody remembers starting. Your whole retirement plan rests on that one figure, and there is a simple test that settles it to the dollar. The window to run this test closes the day you retire. In this episode, I lay out what the test is and how long it takes. Watch this before you build a retirement around a number you guessed at. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary — please consult with your adviser before acting on any information discussed here.

9. 

   24 Aug 2026

   The $0 Financial Tool Nobody Talks About (But Everyone Needs)

   In most households, one person handles the money. They pay the bills, know the passwords, and know which account covers what. It all works right up until that person isn't there anymore. In this episode, I walk through a tool that gets your whole financial life into one place, so the people you leave behind can pick up where you left off. It costs nothing, it takes about an afternoon, and almost no one has one. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary — please consult with your adviser before acting on any information discussed here.

10. 

    17 Aug 2026

    Beneficiary or Trust? How to Choose the Right Path for Each Asset

    There is a form sitting at your bank or your brokerage right now that can override your will. Most people have no idea it is there, and if the name on it is out of date, the money in that account may end up somewhere you never intended. In this episode, I walk through the two main ways an account can pass to the people you love: a beneficiary designation right on the account, sometimes called TOD or POD depending on the account type, or ownership inside a living trust. Both paths can keep your family out of probate court. The difference shows up later, in what your family actually has to do after you are gone, and for certain assets one path is far simpler than the other. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary — please consult with your adviser before acting on any information discussed here.

11. 

    10 Aug 2026

    NEW Backdoor Roth For Kids! (No Job Required)

    There is now a backdoor Roth for kids. No job required. It launched on July 4th, and buried inside it is something the tax code has never allowed before: a way to get Roth money working for a child who has never earned a dollar. No income limits on you, no income limits on the child. The version you have seen in the headlines is a mediocre deal, and I explain why. But there is a second move almost nobody is talking about, and for a narrow group of families it changes the math completely. In this episode I walk through both, run a hypothetical example, and lay out the three filters that decide whether this belongs anywhere near your plan. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- Timestamps: 0:00 Brand New Account 1:03 How Trump Accounts Work 2:25 The Catch 3:51 How It Compares to a 529/Custodial Roth 4:25 The Second Move: Converting to a Roth at 18 6:27 A Hypothetical: $5,000 a Year From Age 2 7:16 Rule of 72 8:03 Who This Strategy is Actually For 10:38 Three Cautions 12:11 Bottom Line ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary — please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. The figures and example shown are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. All investing involves risk, including possible loss of principal. Trump Accounts are a newly enacted program and the rules, including the conversion mechanics discussed here, may be clarified or changed by future guidance. Nothing here is a recommendation to open or fund any specific account.

12. 

    3 Aug 2026

    The Inherited IRA Mistake That Builds a Huge Tax Bill

    An inheritance should make your life easier, but one wrong move with an inherited IRA can hand a big chunk of it back in taxes, and most of that is avoidable. In this episode, I break down the 10-year rule for inherited traditional IRAs: what it actually requires, who it applies to, and the trap that catches many people who assume there's nothing to do until year 10. Using a hypothetical example, I walk through two siblings who inherit the same amount and follow the same rule, yet end up with completely different tax bills because of the one thing they each control, their timing. If you've inherited an IRA, or you know you will someday, this is the video I'd want you to watch before you touch the account. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here.

13. 

    27 Jul 2026

    6 Things to Get in Order Before You File for Social Security

    6 Things to Get in Order Before You File for Social Security You sit down to file for Social Security, hit a wall on something you didn't know you needed, and now you're either putting it off for two more weeks or pushing through a decision you might regret. It happens constantly, and almost all of it is avoidable with a little prep. In this episode, I walk through the six things to get in order before you start your application, the same ones that trip people up again and again in the enrollment meetings I sit through with clients. We cover testing your ssa.gov login before the day you need it, gathering everything the application will ask for, picking your start month, understanding how still working can reduce your benefit, getting your direct deposit details ready, and choosing your tax withholding. Do the prep first, and the application itself is the easy part. You walk in knowing what you're choosing instead of guessing. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. The figures and example shown are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. All investing involves risk, including possible loss of principal.

14. 

    21 Jul 2026

    Why One Withdrawal Can Raise Medicare Costs Later

    You take one larger withdrawal from your retirement account, maybe for a new roof, a trip, or to help one of your kids, and two years later, your Medicare premium goes up and you have no idea why. In this episode, I explain IRMAA, the income-related surcharge that raises Medicare costs for higher-income retirees, and why the two-year delay makes it so easy to get caught off guard. Using a hypothetical example, I walk through a retired couple who take an extra withdrawal, cross the income threshold by just a couple thousand dollars, and end up paying a surcharge for a full year without ever connecting it back to that one decision. Then I share three questions worth sitting with before you take a big withdrawal, and why the only good place to handle this is on the front end, before the money comes out. This isn't about talking you out of spending your money. It's about knowing the full price tag before you decide, including the part that doesn't show up for two years. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- SSA-44 (Medicare IRMAA appeal form): https://www.ssa.gov/forms/ssa-44.pdf ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. The figures and example shown are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. All investing involves risk, including possible loss of principal.

15. 

    21 Jul 2026

    The Roth Conversion Decision You Don't Know About

    A Roth conversion isn't one decision; it's two, and most people only ever make the first one. The question everyone asks is whether to convert and how much. The question almost nobody asks is where the money to pay the tax comes from, and that second choice quietly determines how much of your conversion actually ends up working tax-free for the rest of your life. In this episode, I break down what a conversion really is, then walk through a hypothetical example comparing the two ways to pay the tax: withholding it from the conversion itself, or paying it from cash you already have outside your IRA. Both produce the same tax return, but they leave very different amounts inside your Roth. I also cover an important caution for anyone under 59½, and I finish with five questions worth asking yourself before you convert this year. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and your favorite podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary, please consult with your adviser before acting on any information discussed here. Past performance is not indicative of future results. The figures and example shown are hypothetical, are for illustrative purposes only, and do not guarantee any specific outcome. All investing involves risk, including possible loss of principal.

16. 

    21 Jul 2026

    Welcome to Retirement SimpliFied

    Retirement is the first time in your financial life where the big decisions are actually yours to make, and I've found most of the "help" out there is either too complicated to use or too generic to apply to your life. I created this channel to change that: to take the real decisions people face in retirement and walk through them one at a time, in plain terms. Everything we cover comes from a real question a real client has asked. No apps, no dashboards, just the conversations that actually matter. I'm Eric Sigdestad, a CERTIFIED FINANCIAL PLANNER™ professional and tax preparer in San Diego, and over my career, I've had more than 10,000 conversations with people about retirement. I post a new episode every week on YouTube and podcast platforms. ------------------------------- Subscribe for a new episode every week 🔔 Ready to build a plan that fits your life? Start here → https://www.retiremeasap.com/contact ------------------------------- This content is provided for general educational purposes only and does not constitute personalized investment, tax, or legal advice. SimpliFi, Inc. is an SEC-registered investment adviser (CRD No. 3140614); registration does not imply a certain level of skill or training. Individual circumstances vary; please consult with your adviser before acting on any information discussed here.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

3 ratings

Spotify

5.0 / 5

5 ratings

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Guest appearances

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