Is Financial Software Giving You False Retirement Confidence? - 548

Joe Anderson, CFP® and Big Al Clopine, CPA tackle one of the trickiest timing questions in retirement planning, today on Your Money, Your Wealth podcast number 553: when should you convert to Roth, while you're still earning, or after retirement? First, James from Texas wonders if it's worth maxing out his high-fee 457 plan, or if he's better off investing in a low-cost brokerage account. Full-time travelers "Lois and Clark" want to know how much they should keep converting to Roth now that they're on Medicare. Ray Charles in Chicago is burned out on corporate life and plans to quit at 55. Is that the perfect time for him to start Roth conversions? And finally, Gun and Rose from Louisiana ask if borrowing again from their 401(k) is a smart move. Free Financial Resources in This Episode: https://bit.ly/ymyw-553 (full show notes & episode transcript) Retirement Lifestyles Guide - free download Ultimate Guide to Roth IRAs - free download Will Your Money Last Through Retirement? - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings   Chapters: 00:00 - Intro: This Week on the YMYW Podcast 00:56 - 457(b) vs. Brokerage: Are High Fees Worth the Tax Break? (James, TX) 06:43 - Roth Conversions in Retirement: Hitting the Road and the 12% Bracket ("Lois & Clark", FL) 19:54 - Early Retirement Pivot: Quit at 55 and Convert to Roth? ("Ray Charles", Chicago, IL) 33:28 - Should We Borrow From 401(k) For Home Repairs? (Gun & Rose, LA) 38:54 - Outro: Next Week on the YMYW Podcast  

Joe Anderson, CFP® and Big Al Clopine, CPA tackle the fears that mess with even the best-laid financial plans, today on Your Money, Your Wealth® podcast 552. Big Wallet Barbie and Ken from the Midwest have saved millions, but Barbie's still worried about retiring early, buying a new house, and converting to Roth. Is she second-guessing her plans? The fellas spitball for Dan from Florida, who's flying high in the 35% tax bracket and trying to decide between Roth 401(k) contributions and future Roth conversions. They also float a surprising idea - one that's rare on YMYW - for a listener from Chicago who is FIRE'd Up about Roth vs. pre-tax and making a tax-smart wealth transfer. We'll wrap up with a couple of your comments. Free Financial Resources in This Episode: https://bit.ly/ymyw-552 (full show notes & episode transcript) Emotionless Investing Guide The Truth About Your Love/Hate Relationship With Money - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings   Chapters:  00:00 - Intro: This Week on the YMYW Podcast 00:49 - Big Wallet Barbie and Ken's Roth Conversion, Retirement, and Home Purchase Strategy (Barbie Mattel, Midwest) 08:58 - Roth 401(k) Contributions or Roth Conversions? Flying High in the 35% Tax Bracket (Dan, FL) 17:23 - High-Earners Planning FIRE and Wealth Transfer: Roth, Pre-Tax… Life Insurance? (FIRE'd Up, Chicago) 29:56 - Correction on Spousal Social Security Benefits After the Fairness Act (Cindy) 33:37 - Follow Up: The Kids Are Pretty Alright (Lucas, MN) 34:44 - Outro: Next Week on the YMYW Podcast

We're playing "which comes first" today on Your Money, Your Wealth® podcast number 551 with Joe Anderson, CFP® and Big Al Clopine, CPA. "Retired G-Man and Nurse Ratched" from Pennsylvania have saved $2 million. Should they withdraw money first from their IRA or their taxable accounts in retirement? "Mike and Carol in Florida" want to know when and how much to convert to Roth, but they're also sitting on a mountain of company stock. Should they deal with that first? Mackey in Florida is 55 and wonders if he can retire now with $2.6 million and some lingering debt - but there's an important first he's missing too! Plus, Mike in Utah asks Joe and Big Al to spitball on a plan for his 90-year-old mom's $1.9 million annuity, and Doc McMuffin in Minnesota asks for the fellas' take on her plan to gift appreciated assets to her parents. Free Financial Resources in This Episode: https://bit.ly/ymyw-551 (full show notes & episode transcript) YourMoneyYourWealth.com - all our financial resources! Ask Joe and Big Al, blogs, workshops, financial guides, and 11 seasons of YMYW TV! 10 Big Retirement Regrets to Avoid (Before It's Too Late) - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings   Chapters:  00:00 - Intro: This Week on the YMYW Podcast 00:53 - How to Retire at 55 With $2.6M and Debt? First, How to Write a Good Spitball Request (Mackey, FL) 03:46 - Sequence of Retirement Withdrawals: IRA First or Taxable First? (G-Man and Nurse Ratched, PA) 12:10 - Roth Conversions vs Concentrated Stock: Which Comes First? (Mike & Carol, FL) 29:27 - What to Do With 90-Year-Old Mom's $1.9M Annuity? (Mike, UT) 40:59 - Is Gifting Appreciated Assets to Parents Tax-Smart or Risky? (Doc McMuffin, MN) 48:27 - Outro: Next Week on the YMYW Podcast

Joe and Big Al spitball on how to avoid screwing up the timing of your Roth conversions, today on Your Money, Your Wealth® podcast number 550. Barrie from New York is 62 and single, and she's been diligently converting pre-tax money each year for lifetime tax-free Roth growth. Should she continue after she retires next year?  "Jerry and Elaine" want to retire in the next six years and still leave the kids an inheritance. When should they start Roth conversions? Alex in Pennsylvania is a 31-year-old software engineer. Should he convert his IRA to Roth all at once? Plus, how can he transition into a career as a financial planner? A clarification on the age plus 20 rule of thumb for retirement contributions from one of our YouTube viewers is very un-clarified for Joe, and the fellas let Lisa in San Diego know whether she can use her rental real estate income to fund a Roth 401(k). Free Financial Resources in This Episode: https://bit.ly/ymyw-550 (full show notes & episode transcript) Ultimate Guide to Roth IRAs 6 Signs You Truly Have "Enough" for Retirement - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings Chapters: 00:00 - Intro: This Week on the YMYW Podcast 00:55 - Should I Keep Converting $20K a Year in Retirement? (Barrie, NY) 07:17 - Can We Retire at 62 and Still Leave an Inheritance? Roth Conversion Strategies for Big Accounts (Jerry & Elaine, KS) 17:05 - I'm 31. Should I Convert $57K Now or Spread It Out? (Alex, PA) 29:12 - Roth Conversion Timing Before Retirement (Mike, Philly Suburbs) 36:49 - Confused About Roth Withdrawal Rules at 60 (Lisa, Omaha NE) 40:05 - Clarification on the Age + 20 Rule of Thumb for Contributions (Matt, YouTube) 45:40 - Can Rental Property Income Fund a Roth 401(k)? (Lisa, San Diego) 47:24 - Outro: Next Week on the YMYW Podcast

Today on Your Money, Your Wealth® podcast number 549 with Joe Anderson, CFP® and Big Al Clopine, CPA, a comment on one of our YouTube videos sparks a dialogue between Joe and Big Al on the 4% rule vs. the "guardrails" withdrawal strategy. Joe at the Beach is managing his ~$6M portfolio on his own, but wants the fellas' take on his upper limit for yearly spending, so he can keep drinking his old-fashioneds. Can Joe Ko in Virginia afford to bridge the gap between retiring at 67 and taking Social Security at 70? Plus, "Harold and Maude" have nearly $7M saved. Should they accelerate Roth conversions into high-tax brackets before moving from low-tax Colorado to high-tax California? And how much more than their current annual spend can they afford for family vacations and travel? Free Financial Resources in This Episode:  https://bit.ly/ymyw-549 (full show notes & episode transcript) Withdrawal Strategy Guide Cruising Into Retirement Checklist and Guide (limited time offer, download by this Friday!) How to Cruise Into Your Retirement - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings   Chapters: 00:00 - Intro: This Week on the YMYW Podcast 00:50 - What About the Guardrails Withdrawal Strategy? (Bill, YouTube) 04:13 - I'm 69 with $5.7 Million Saved. What's the Max I Can Spend in Retirement? (Joe at the Beach) 15:12 - 63 and 58 With $1.85M Saved. How Much Can We Spend from 67 Until Social Security at 70? (Joe Ko, VA) 21:30 - We're 61 and 69 with $7.6 million. Can We Increase Our Retirement Spending? How Should We Do Roth Conversions? ("Harold and Maude", Durango, CO) 33:49 - Outro: Next Week on the YMYW Podcast

Wendy and Joe in Colorado ran the numbers, and their financial planning software says they'll have over $10 million when they pass. Wendy's wondering if they should continue converting to Roth while working, despite their high tax bracket. But has the software lulled them into a false sense of security? That's today on Your Money, Your Wealth® podcast number 548 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, which is smarter for "Kurt and Courtney" in New York: aggressively paying down their mortgage, or putting their extra money to work in the market before Kurt retires early in 20 years? Finally, when does it stop making sense for high-earners "Tim and Faith" in Boston to contribute to their Roth? The fellas duke it out on this one (and we figure out, based on our earliest musical interests, which era we're each children of.) Free Financial Resources in This Episode: https://bit.ly/ymyw-548  (full show notes & episode transcript) Pay Off the Mortgage? - YouTube playlist - Spotify playlist DOWNLOAD The Retirement Readiness Guide WATCH 4 Hard Truths About Retirement You Need to Face on YMYW TV Financial Blueprint (free, self-guided) Financial Assessment (free, meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings   Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:11 - Financial Software Says We'll Have $10M. Should We Continue Converting to Roth While Working, Despite Our High Tax Bracket? (Wendy, Loveland, CO) 16:35 - Watch 4 Hard Truths About Retirement You Need to Face on YMYW TV, Download the Retirement Readiness Guide 17:37 - What Are the Pros and Cons of Paying Off Our Home Before I Retire Early? (Kurt & Courtney, NY) 31:54 - Pay Off the Mortgage: YMYW Podcast Playlists on YouTube and Spotify, Calculate your free Financial Blueprint 32:51 - We're Late 40s With $3M + $2M RSUs. Continue Contributing to Tax-Deferred? Are We On Track for Retirement at 55 or 60? (Tim & Faith, MA) 46:15 - Next Week on the YMYW Podcast 46:37 - YMYW Podcast Outro

A YMYW listener from Missouri and his wife are retired at 69 and 67, with less than $2 million dollars. Should they continue converting retirement savings to Roth for the tax-free growth? What should they do about long term care insurance? More importantly, is our listener's name (Cousy) pronounced "Cuzzy" or "Koozy"? Speaking of Roth conversions, must "Peggy Hill" wait five years to withdraw her conversion money, or only its earnings? That's today on Your Money, Your Wealth® podcast number 547 with Joe Anderson, CFP® and Big Al Clopine, CPA. Plus, is Skipper's retirement payout plan the killer deal he thinks it is? How can Jeff in Dallas pay less capital gains tax on his 3 million dollar single stock, million dollar 401(k), and potential eBay income? Is selling on eBay still a thing? Does Dolly in Tennessee need to empty her inherited IRA within the next 10 years due to the SECURE Act? And finally, HSA vs. HRA: how should Larry in Rhode Island navigate switching from his current employer's health savings account to his future employer's health reimbursement arrangement? Free Financial Resources in This Episode:  https://bit.ly/ymyw-547 (full show notes & episode transcript) 5 Year Rules for Roth IRA Withdrawals 2025 Key Financial Data Guide (newly updated with One Big Beautiful Bill changes) 10 Steps to Improve Investing Success What to Do When the Stock Market Gets Crazy - YMYW TV Financial Blueprint (self-guided) Financial Assessment (Meet with an experienced professional) REQUEST your Retirement Spitball Analysis DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter   Connect With Us: YouTube: Subscribe and join the conversation in the comments Podcast apps: subscribe or follow YMYW in your favorite Apple Podcasts: leave your honest reviews and ratings   Chapters: 00:00 - Intro: This Week on the YMYW Podcast 01:11 - Should We Continue Roth Conversions in Retirement? What About Long-Term Care? (Cousy, MO) 13:03 - Must I Wait 5 Years to Withdraw My Roth Conversion, Or Only Its Earnings? ("Peggy Hill", MN) 21:50 - Is My Retirement Plan Payout the Killer Deal I Think It Is? (Skipper) 28:07 - How to Minimize My Capital Gains Tax? (Jeff, Dallas, TX) 33:37 - Must I Empty My Inherited IRA Within 10 Years With The SECURE Act? (Dolly, Bristol, TN) 37:50 - HSA and HRA: Health Savings Account vs. Health Reimbursement Arrangement (Larry, RI) 40:48 - Outro: Next Week on the YMYW Podcast

We heard your feedback, and today on Your Money, Your Wealth® podcast number 546, Joe Anderson, CFP® and Big Al Clopine, CPA are spitballing retirement for the not-so-fat wallets: Joe and Masako in Washington state and Reid in Indiana have less than a million saved. Can they still accomplish their retirement goals in their 60s? Mr Buckeye in Ohio and Old Macdonald in Maine have less than a million saved, and Curt in Pennsylvania has less than $1.5 million saved. Can they retire early - in their 40s and 50s?    Free financial resources & episode transcript: https://bit.ly/ymyw-546 DOWNLOAD The Going Solo Guide WATCH Going Solo: Navigating Your Financial Future Single on YMYW TV CALCULATE your free Financial Blueprint SCHEDULE your Free Financial Assessment ASK Joe & Big Al for your Retirement Spitball Analysis LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast 00:36 - We're 59 and 65 with Less than $1M. Can We Still Accomplish Our Retirement Goals? (Joe and Masako, WA state) 08:18 - We're 33 with $200K. Can We Retire at 65 and Spend $159K/Year? (Reid, IN) 15:58 - Calculate your Free Financial Blueprint 16:32 - We're Early 40s With $795K. Can We Retire at 55? (Mr Buckeye, OH) 28:38 - Watch Going Solo: Navigating Your Financial Future Single YMYW TV, Download the Going Solo Guide 29:25 - I'm 43 With $50K and a Paid Off House. Can I Retire ASAP? (Old MacDonald, Limington, Maine) 37:35 - I'm 35 With $1.4M. Can I Retire at 45 and Spend $75K/year? (Conshohocken Curt, PA) 49:04 - Next Week on the YMYW Podcast 49:23 - YMYW Podcast Outro

One Big Beautiful Bill is now law. How does it impact your Roth conversion strategies and other financial decisions? Plus, you may have seen or heard other advisors talking about their strategies for getting your retirement savings into tax-free Roth accounts. How are these different from a good ol' Roth conversion, and what do Joe and Big Al think of them? Find out today on Your Money, Your Wealth® podcast number 545 with Joe Anderson, CFP® and Big Al Clopine, CPA. Also, why is Ed Slott, CPA, the man known to many as "the IRA guru," such a fan of permanent cash value life insurance? Finally, an attempted correction from a YMYW YouTube viewer turns into a rousing game of death trivia, and we'll share some of your opinions from the 8th Annual YMYW Podcast Survey, which just closed. (Congratulations Larry, for being the randomly-chosen winner of the $100 Amazon e-gift card, just for completing the survey!) Free financial resources & episode transcript: https://bit.ly/ymyw-545 DOWNLOAD The Ultimate Guide to Roth IRAs WATCH Your 11 Step Path to Financial Freedom on YMYW TV CALCULATE your free Financial Blueprint SCHEDULE your Free Financial Assessment ASK Joe & Big Al for your Retirement Spitball Analysis LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter

You've heard Joe and Big Al talk about the benefits of tax diversification in retirement. That is, having money in tax-deferred, tax-free, and taxable accounts. But what should you do if this tax triangle of yours is lopsided? Joe and our special guest co-host, Marc Horner, CFP®, spitball on this quandary for Rae and Roy in Central California, today on Your Money, Your Wealth® podcast number 544. Plus, do Rae or Roy need to get a part-time job? Also, "Elwood Blues" in Illinois would like to retire in two years, but is willing to go for 3 more to make his retirement plan work. Joe and Marc spitball on when "Elwood" can really put down that harmonica. Free financial resources & episode transcript: https://bit.ly/ymyw-544 Complete the 8th Annual YMYW Podcast Survey by 5pm Pacific on August 31, 2025, for your chance at a $100 Amazon e-gift card! (secret password: ymyw) WATCH 15 Maneuvers to Duck an Unplanned Early Retirement Knockout on YMYW TV CALCULATE your free Financial Blueprint ASK Joe & Big Al for your Retirement Spitball Analysis SCHEDULE your Free Financial Assessment LEAVE YOUR HONEST RATINGS AND REVIEWS on Apple Podcasts SUBSCRIBE or FOLLOW on your favorite podcast app JOIN THE CONVERSATION on YouTube DOWNLOAD more free guides READ financial blogs WATCH educational videos SUBSCRIBE to the YMYW Newsletter Timestamps: 00:00 - Intro: This Week on the YMYW Podcast with Joe Anderson, CFP® and Marc Horner, CFP® 00:49 - Our Tax Triangle is Lopsided. Should One of Us Get a Part-Time Job? (Rae and Roy, Central CA) 12:03 - Watch 15 Maneuvers to Duck an Unplanned Early Retirement Knockout, Calculate your Financial Blueprint, Schedule a Financial Assessment 13:11 - I'd Like to Retire in 2 Years. Willing to Work 3 More to Make it Work (Elwood Blues, IL) 27:10 - Next Week on YMYW Podcast: The One Big Beautiful Bill + More 27:40 - YMYW Podcast Outro