Early Retirement Roadmap

Monthly Dividend ETFs for retirement income can look like a paycheck—but it’s often an illusion. In this episode, I share 3 tests to avoid costly mistakes and keep Affordable Care Act (ACA) taxes in mind. You’ll learn: • The 4 main types of monthly income ETFs (covered-call, high-dividend stock, preferred stock, bond funds) • Why yield can mislead if you ignore total return • Test #1: What the distribution is made of (dividends, interest, option premium, return of capital) • Test #2: Whether monthly payouts increase your control—or reduce it • Test #3: How monthly distributions can raise modified adjusted gross income (MAGI) and affect tax planning Examples include JEPI/JEPQ/QYLD/XYLD/RYLD, SPHD/DIV/SDIV, PFF/PGX/PFFD, and BND/AGG/LQD. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 👉 Free Resources Mentioned: ✅ 12 Must-Do Steps to Retire Sooner and Smarter (Checklist) A simple, practical roadmap to help you get retirement-ready faster. 🔗 Download it here  ✅ Free MAGI & Tax Estimator Spreadsheet (for ACA + taxes) Estimate your Modified Adjusted Gross Income (MAGI), keep an eye on ACA subsidy eligibility, and get a rough tax estimate as you go through the year. 🔗 Get the spreadsheet here  📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 More from me: All my videos, podcast episodes, and freebies: https://mikeupland.com 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

Wondering if you really have enough to retire? In this early retirement planning episode, I break down 6 levels of retirement wealth—from Survival to Fulfillment—so you can see which level you’re at and what it takes to move up. Too many people only ask, “Do I have enough to retire?” when the better question is, “Enough for what level of retirement?” In this episode, I walk through my framework of Survival, Stability, Comfort, Security, Freedom, and Fulfillment Wealth so you can stress-test your plan, avoid white-knuckle retirement, and aim for a life that actually feels secure, free, and meaningful. We’ll also look at a real-world example couple who wants about $75,000/year in retirement spending and how different portfolio sizes can land them at very different levels. You’ll learn: Why “just covering the bills” can trap you in Survival or Stability Wealth What Comfort Wealth feels like—and why it can still be fragile Why I see Security Wealth (Level 4) as a strong target before you retire How Freedom and Fulfillment Wealth shift your focus from “Can we afford this?” to “Does this fit the life we want?” How your withdrawal rate, cash buffer, debt, housing, and health insurance all affect your level How to use this framework as a targeting system, not a report card I’ll also share why, for many people, retiring a bit earlier at Level 4 with more healthy years can be more valuable than grinding your way to Level 6 but having less time and energy to enjoy it. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 👉 Free Resources Mentioned: ✅ 12 Must-Do Steps to Retire Sooner and Smarter (Checklist) A simple, practical roadmap to help you get retirement-ready faster. 🔗 Download it here  ✅ Free MAGI & Tax Estimator Spreadsheet (for ACA + taxes) Estimate your Modified Adjusted Gross Income (MAGI), keep an eye on ACA subsidy eligibility, and get a rough tax estimate as you go through the year. 🔗 Get the spreadsheet here   📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 More from me: All my videos, podcast episodes, and freebies: https://mikeupland.com 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.  

Future-proof your retirement with habits of thriving retirees, early retirement planning tips, and simple retirement investing strategies to help you feel confident about the decades ahead. In this episode, I break down 9 practical habits I myself do and see over and over again in retirees who are not just “getting by,” but actually thriving—financially, emotionally, and health-wise. We’ll talk about how to spend intentionally instead of fearfully, why a 2–4 year “sleep at night” cash buffer can keep you calm during market downturns, and how to treat your health like a core investment, not an afterthought. We’ll also cover purpose, simplicity, and risk management—so your retirement isn’t wiped out by one bad market, one bad policy change, or one bad life event. What you’ll learn: • How to future-proof your retirement with flexible spending “guardrails” • Why thriving retirees protect their sleep-at-night money   • The key health habits that support a long, active retirement • How to retire to something, not just from your job • Why you don’t need a complex portfolio—just a simple, understandable system • Overlooked risks (insurance, documents, fraud) that can derail retirement • How to set up regular financial check-ins without obsessing over the market If you’re planning to retire early—or you’re already retired and want a calmer, more confident path forward—this episode will help you put simple habits in place so you can enjoy your money and your life. Lazy retirement investing made simple: early retirement, index funds (VTI, VOO, VUG, VIG, VYM), withdrawal rate guardrails, 2–4 year cash liquidity runway, Roth conversions, MAGI/ACA & IRMAA tax strategy. Ready for a “do less, retire better” portfolio? In this episode, I walk through my lazy retirement investing plan—built for early retirees and anyone who wants a low-maintenance, rules-based retirement approach that’s diversified, tax-smart, and actually livable. We’ll set up a 3-category index portfolio, place assets for taxes, build a 2–4 year cash runway for bear markets, and use flexible withdrawal guardrails so you can sleep at night and still enjoy life. What you’ll learn: The “lazy” portfolio (Foundational, Growth, Income) and why boring wins long-term Examples to research: VTI/VOO (core), VUG (growth), VIG/VYM (dividends) How to set your mix and rebalance (±5% bands / annual check-in) Smart tax placement: ETFs in taxable, bonds/REITs in tax-advantaged, avoid surprise cap gains from index mutual funds in taxable Building a 2–4 year liquidity runway (cash, CDs, short-duration TIPS) Choosing a starting withdrawal rate (e.g., ~3% for longer retirements) + ±20% guardrails Practical withdrawal order (taxable → traditional → Roth) Roth conversions: when they can make sense and how to manage MAGI for ACA subsidies pre-65 and IRMAA after 65 The annual tune-up: rebalance, refill runway, run a tax/MAGI check, adjust withdrawals, and basic account hygiene Free resources mentioned in this episode: 🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.  🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. 🎧Listen to these episode titles I mentioned in this podcast:  - My Lazy Retirement Investing Plan (Season 3, Episode 1) - ACA MAGI: How to Calculate & Manage It for Big Savings! (Season 2, Episode 14)   💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you!   ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!   📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1   🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/   ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)   DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.        

Does retiring early reduce Social Security? The truth—how benefits are really calculated: the 35-year rule, Average Indexed Monthly Earnings (AIME), bend points, indexing only through age 59, and why “zeros” hurt. In this episode, I break down: Why Social Security is based on your highest 35 indexed years—not your last job. How indexing stops after age 59, so skipping some early-60s work years often matters less than headlines suggest. Why zeros are the enemy—and simple ways part-time income can replace them. A clear Path A vs. Path B example (keep working vs. hang it up) to show how the impact often lands in the couple-hundred-per-month ballpark in my scenario. The crucial difference between retiring and claiming (FRA reductions vs. delayed credits). Quick checklist to get clarity: Download your earnings record at SSA.gov and fix any errors. Count your credited years—if you’re under 35, plan to replace zeros (even modest earnings help). Compare two scenarios: keep working a bit vs. retire earlier; check benefits at Full Retirement Age and at your actual claim age. Decide based on dollars and lifestyle, not fear headlines. Free resources mentioned in this episode: 🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.  🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. 🎧Listen to these episode titles next that I mentioned in this podcast:  How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! ACA MAGI: How to Calculate & Manage It for Big Savings! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.  

Retirement planning, early retirement, 7 signs you’re ready to retire, retire earlier than you think, retire in your 50s, how to retire early—here’s how to know if the numbers and lifestyle say YES. If you’re wondering “Am I actually ready to retire sooner?”, this episode walks through 7 clear signs—financial, lifestyle, and mindset—that indicate you can retire earlier than you think. We’ll cover bridging to age 59½, penalty-free access options (Rule of 55 and Substantially Equal Periodic Payments under IRS Rule 72(t)), income diversification, healthcare planning, Monte Carlo stress tests, and a low-risk way to “test-drive” retirement before you leap. What you’ll learn: • Why 59½ is a key milestone—and smart ways to bridge those years • Penalty-free access paths: Rule of 55 and 72(t) SEPPs (complex, not for everyone) • How diversified income (cash, taxable brokerage, dividends/cap gains, Roth basis) boosts flexibility • Stress-testing your plan with Monte Carlo simulations to validate your withdrawal rate • Housing decisions (right-sizing or staying put) and their impact on cash flow • Healthcare budgeting before Medicare and how to plan for premiums/out-of-pocket costs • A simple “retirement test-drive” to build confidence before you quit Free resources mentioned in this episode: 🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.  🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. 🎧Listen to these episode titles next that I mentioned in this podcast:  How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! ACA MAGI: How to Calculate & Manage It for Big Savings! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.    

2026 health insurance: If Affordable Care Act (ACA) subsidies end, Plan A vs Plan B. Open Enrollment Nov 1; enroll by Dec 15 for Jan 1. MAGI targets, 400% FPL, on-exchange vs off-exchange. In this video,“No Subsidies in 2026? Plan A vs Plan B (Do This)”— I provide two pathways   so you’re ready to enroll by Dec 15 for a Jan 1 health insurance start,  and why I’m building both plans now given the uncertainty around enhanced ACA subsidies. Plan A (assume no enhanced subsidies): A1: On-exchange, ACA-compliant coverage even without credits (keeps ACA protections). A2: Off-exchange, ACA-compliant quotes (compare carefully; note that off-exchange doesn’t receive credits if they return mid-year). A3: “Alternatives” with caution (e.g., short-term, cost-sharing, memberships/DPC): understand pre-existing condition limits, exclusions, and red flags. Only as a time-boxed fallback. Plan B (if enhanced subsidies continue): Manage MAGI like a pro: right-size year-end Roth conversions, time capital gains, and use taxable brokerage for spending to avoid accidental income spikes. If working: lean on pre-tax payroll options and an HSA (with an eligible HDHP) to help control MAGI. If retired: be deliberate with pre-tax withdrawals—they raise MAGI and can shrink credits, also contribute to an HSA. 📊Free resources mentioned in this episode: 🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. 🔗ACA Cost Estimator 🔗2025 Federal Poverty Level Guidelines 🔗Goto healthcare.gov or your state exchange to enroll in a 2026 ACA plan - open enrollment begins Nov 1.   🎧Listen to these podcasts of mine next for more info on the topics covered in this episode: ACA MAGI: How to Calculate & Manage It for Big Savings! Will ACA Subsidies Disappear After 2025? What You NEED to Know! The $12,900 Health Insurance Loophole for Early Retirees! Health Insurance Options for Early Retirement: What You NEED to Know How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake) 🔔 If you found this helpful, please subscribe & leave a review, or support me with a cup of coffee here.  💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin.  It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 🎥 When you’re not on the go, check out Mike’s Early Retirement Roadmap YouTube channel for more insights and inspiration.   🌐  Visit MikeUpland.com – Connect with Mike & explore retirement resources.

Retirement planning: 5 things to sell before you retire—downsize the house, cut support for adult children, ditch RV/boat “toys,” drop the second car, and release your work identity with my Keep-Sell-Swap test. If you want a calmer, freer retirement, subtraction beats addition. In this video I walk through five high-impact things to sell (or stop funding) to lower ongoing costs, reduce stress, and buy back time for what matters most—travel, family, health, and fun. What you’ll learn: • How to decide if your house is sized for your next chapter • A smart boundary for funding independent adult children without hurting your plan • Cheaper alternatives to ownership (boat clubs, rentals, peer-to-peer) • A simple test to see if you still need a second car • Why letting go of your old work identity creates real freedom My 3-step Keep, Sell, or Swap framework: Does this serve my next chapter—or my last one? What’s the real all-in cost (cash, time, stress, space, opportunity)? What becomes possible if I release it? Try the 60-Day Swap: live exactly as if the item is gone (park the RV, ignore the second car, use rentals). Track real inconveniences vs. habit itches. Decide with data, not guilt. 🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.  🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.  

Retirement planning, early retirement, money traps: timeshares, vacation homes, high-fee annuities, whole life insurance, long-term care insurance, high-yield bonds, high-fee active funds, cash flow, withdrawal rate. In this episode, we break down 7 “assets” rich retirees avoid—and why skipping them protects your cash flow and flexibility before and after you retire. You’ll learn how these purchases can raise ongoing costs, lock up money, or add risk at the worst time—and what simpler choices to use instead. What you’ll learn: Timeshares & vacation homes: exchange fees, rising dues/carrying costs, weak resale; why renting keeps flexibility High-fee annuities: layers of fees, surrender schedules, complex crediting; why simple, low-cost portfolios + a cash buffer win Whole life insurance (late start): high premiums, slow cash value; why separating insurance from investing helps cash flow Long-term care insurance: premium hikes, ADL triggers, fine print; when a dedicated LTC bucket (cash/short-term bonds/TIPS) can be a cleaner path High-yield corporate bonds: higher default risk right when stability matters; use high-quality bonds for ballast instead High-fee active funds: expense ratios and taxes drag; low-cost index funds tend to outperform over time 🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.  🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.

I retired early at 55. In this episode I show exactly how to retire early with 5 proven keys to early retirement: the mindset that powers compounding, how to raise your savings rate, the income multiplier, simple investing with low-cost index funds, and retirement planning that avoids sequence-of-returns risk. If you want to retire early—or just build a larger retirement nest egg—this step-by-step guide covers the Rule of 72, defense vs. offense budgeting, lifestyle-creep control, rental real estate and REITs, cash reserves, and the 4% rule vs. updated safe withdrawal rates and more! These early retirement strategies, investing basics, and financial independence tactics will help you retire early, invest smarter, and create reliable retirement income. What you’ll learn: • Key #1: Mindset and the power of compounding (Rule of 72) • Key #2: Defense + offense budgeting to boost your savings rate • Key #3: The income multiplier—raises, promotions, and skill stacking • Key #4: How to invest for retirement (index funds, value funds, real estate, REITs. etc) • Key #5: Know your number (4% rule, Bengen update, guardrails, cash buffer) 🔗Click here for my free checklist 12 Must – Do Steps to Retire Sooner and Smarter.  🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.   ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.  

ACA MAGI explained: how to calculate and manage Modified Adjusted Gross Income (MAGI) for Affordable Care Act (ACA) subsidies—step-by-step, with a free MAGI calculator to lower premiums and maximize premium tax credits/subsidies. In this episode, we calculate ACA MAGI step-by-step using a real early-retiree scenario and show you how to keep ACA premiums low by hitting your MAGI “sweet spot.” You’ll learn: • What counts in MAGI vs. what doesn’t. • How to add back non-taxable Social Security benefits, tax-exempt interest, and excluded foreign income. • How Roth conversions, IRA withdrawals, dividends, interest, and capital gains flow into AGI and then ACA MAGI. • Form 8962 (reconciling with 1095-A) essentials. • How to plan for the 2026 subsidy cliff as the 400% FPL cap returns. 🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. 📊 Resources mentioned in this episode:  More information on Traditional IRA contribution limits and the ability to deduct them: Traditional IRA Contribution Limits for 2025 - NerdWallet IRS Publication 501: 2024 Publication 501 2025 FPL Levels based on household size: detailed-guidelines-2025.pdf Click here for the ACA Cost Estimator 🎧 Podcast episodes mentioned:  This podcast episode where I talk about about using the ACA cost estimator and saw amazing results, including cost sharing reductions by controlling MAGI, titled: How Early Retirees Can Pay WAY Less for Health Insurance! This podcast episode on how a taxable brokerage account can be a superhero in reducing MAGI for ACA, titled: The $12,900 Health Insurance Loophole for Early Retirees! This podcast episode that goes into detail about the enhanced ACA subsidies likely expiring at the end of 2025, and the 400%FPL cliff returning in 2026, titled: Will ACA Subsidies Disappear After 2025? What You NEED to Know! ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.    

Roth conversions vs. ACA subsidies is the early retirement dilemma no one talks about. If you’re planning for early retirement, you need to know how Roth IRA conversions can raise your MAGI and cost you ACA health insurance subsidies before Medicare. In this episode, I’ll break down the trade-off, show you real examples, and share strategies to balance Roth conversions and Affordable Care Act subsidies. Retiring before 65 means health insurance is one of your biggest expenses. Should you save thousands on ACA subsidies today, or avoid massive RMD taxes later with Roth conversions? I’ll cover how subsidies work, how Roth accounts impact your Modified Adjusted Gross Income (MAGI), and what happens if enhanced subsidies expire after 2025. What you’ll learn: • Why Roth conversions are so popular in retirement planning • How ACA subsidies are calculated and why MAGI matters • Real-world examples of couples facing this Roth vs. ACA trade-off • Strategies like partial Roth conversions to protect subsidies • What changes when enhanced ACA subsidies end in 2026 This is one of the most important — and overlooked — retirement planning dilemmas. Listen to see if protecting ACA subsidies or prioritizing Roth conversions is smarter for your retirement strategy. 🎧 Listen to the following episodes mentioned in this podcast for more info that you'll find as show episodes:  - Health Insurance Options for Early Retirement: What You NEED to Know - How Early Retirees Can Pay WAY Less for Health Insurance! 🎧 And listen to these other episodes about health insurance in early retirement that are full of great information you can't miss!:  - The $12,900 Health Insurance Loophole for Early Retirees! -  Will ACA Subsidies Disappear After 2025? What You NEED to Know!   📊 Here is the link to the ACA cost estimator tool mentioned : https://www.healthcare.gov/see-plans/#/ 📊2025 Federal Poverty Level Guidelines: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #RothIRA #ACASubsidies #EarlyRetirement    

Early retirement at 55 comes with financial and lifestyle challenges most people don’t expect. In this video, I share 5 things I wish I knew before retiring early, including lessons on retirement planning, healthcare costs, spending habits, and mindset shifts that can make or break your retirement years. Retiring early isn’t just about saving enough money — it’s about knowing how to spend wisely, manage healthcare, and protect your peace of mind. If you’re planning for early retirement (or thinking about retiring at 55 like I did), these insights will help you avoid regrets and set realistic expectations for the journey ahead. What you’ll learn in this video: • Why retiring early feels different than expected • The financial and emotional lessons I wish I knew before retiring • How healthcare, spending habits, and mindset can shape your retirement • Tips for avoiding common regrets in early retirement ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #retiringearly #earlyretirement #retirementplanning

Working past 60 might seem smart, but it could be the biggest retirement mistake you make. In this video, we reveal the hidden costs of working past 60 — from lost health years to missed financial opportunities — and how to find your perfect retirement timing. You’ll learn why the payoff for working longer can shrink after age 60, how taxes and Medicare premiums eat into those extra earnings, and why your healthiest years may be slipping away. Plus, I’ll share real-life examples, surprising data, and a practical framework for deciding when it’s truly time to retire. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! Resources Mentioned: 📊 New York Life Study: https://time.com/3821757/this-is-the-retirement-regret-nobody-talks-about/ 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #WorkingPast60 #RetirementPlanning #EarlyRetirement

Wondering how the 2025 tax law changes affect your retirement strategy? This video breaks down the One Big Beautiful Bill Act, a landmark tax bill signed into law by President Trump — and its HUGE implications for retirees, early retirees, and anyone planning for financial independence. 📌 Here’s what you’ll learn: 🏦 2025 retirement tax changes that lock in the 2017 Tax Cuts and Jobs Act (TCJA) permanently 💰 Extended income tax brackets, standard deduction increases, and the brand-new senior tax deduction 🧾 Detailed breakdown of Child Tax Credit enhancements, AMT exemption, SALT cap increase, and capital gains tax stability 🚗 New 2025-2028 deductions for auto loan interest, tip income, and overtime pay 🏥 What the bill didn’t do: the ACA subsidy cliff and how it could affect early retirees in 2026 💼 How to optimize Roth conversions, HSA contributions, and long-term retirement planning This is the 2025 retirement tax update you can’t afford to miss — I did all the research so you don’t have to! If you’re nearing retirement or in early retirement, these tax changes for retirees in 2025 could seriously impact your strategy. Make smarter money moves with clarity and confidence. ✅ ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #RetirementTaxChanges #2025TaxUpdate  #EarlyRetirementPlanning, #SeniorTaxDeduction #OneBigBeautifulBill

Want early access to your 401(k) or IRA before age 59½ without getting slammed by the IRS 10% penalty? In this episode, I’ll walk you through the IRS Rule 72(t)—a little-known but completely legal loophole that allows penalty-free early withdrawals through SEPP (Substantially Equal Periodic Payments). This strategy could unlock your early retirement plans—but beware, the rules are strict and the risks are serious. ✅ We’ll cover: How IRS Rule 72(t) works with IRAs and 401(k)s Eligibility requirements and account types How long you must commit to fixed withdrawals Major risks including sequence-of-returns and tax traps When Rule 72(t) makes sense—and when it absolutely doesn’t If you're aiming for early retirement and don’t qualify for the Rule of 55 or have limited brokerage/Roth options, Rule 72(t) could be your lifeline. But it can also backfire if you’re not careful. ⚠️ Don’t attempt this without consulting a tax pro or retirement planner—this is one of the most complex strategies out there. 🎁 Download my free guide: 12 Must-Do Steps to Retire Sooner and Smarter. Whether you're just getting started or refining your plan, this free guide will help you take the next step! It's a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q  I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.   #EarlyRetirement #401kWithdrawal #IRSRule72t #RetirementPlanning #FinancialFreedom

Are you really ready for retirement? As your retirement countdown begins, I reveal the critical steps you must take to ensure you're fully prepared to retire confidently and securely. From defining your retirement vision to setting a realistic retirement age, I cover everything you need to know for effective retirement planning. In this retirement planning video, you’ll discover: How to pick the ideal retirement age (55, 59½, or 62) to maximize your retirement savings and avoid penalties. Essential budgeting strategies for retirement, including accurately planning for healthcare expenses before Medicare. Proven methods to calculate your FIRE number, going beyond the standard 4% rule for early retirement success. Powerful risk-management techniques to protect your nest egg from sequence of returns risk and market volatility. Crucial insights about when to claim Social Security, and how avoiding a common trap could save you thousands. Get started with my free checklist, "12 Must-Do Steps to Retire Sooner and Smarter," to ensure you don't miss a thing as you prepare to retire: 👉 https://payhip.com/b/IBj3q Stress-test your retirement plan using the highly recommended retirement planning software (Boldin) mentioned in the video: Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! 📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.  #CountdownToRetirement #RetirementPlanning #EarlyRetirement #RetirementChecklist #SocialSecurityTips

Thinking about early retirement? Here are 6 powerful reasons to retire early—covering retirement planning, financial freedom, health, and why waiting longer could cost more than money. Whether you're close to retiring or just exploring the idea, these insights might change how you think about work, money, and time. Inspired by the popular topic “5 reasons to retire early,” this episode takes it further—showing why waiting even one more year could cost you more than just money. We’ll explore the opportunity cost of continued work, how your health and freedom are affected, and why arbitrary retirement goals may be holding you back from the financial independence you’ve already earned. I retired early at 55, and in this episode, I’ll share the reasons that finally made me take the leap—and how it’s changed my life, and that you should consider too. 👉 If you’re ready to rethink your retirement timeline, this video is for you.  ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful! 💼 My Favorite Retirement Planning Tool, and that I mentioned in this episode! If you’re serious about planning for retirement, you’ve got to check out Boldin. It’s a powerful tool that helps you map out your financial future—whether you’re a DIY planner or just want to stress-test your retirement strategy. 👉 Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I earn a small commission if you decide to go on the paid plan after a free 2-week trial, or you can remain on the free plan, but I highly recommend the paid plan to use all its robust features! I personally use it for my retirement planning and love it! This link doesn’t cost you anything extra and helps to support the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺 When you're not on the go, check out my Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #earlyretirement #retireearly #financialfreedom #retirementplanning #retirement

🚨 Roth Conversion Warning: Miss This 2025 Window, Regret It FOREVER! In this episode, I break down why Roth conversions in 2025 are more important than ever—and how early retirees, those already retired, or those thinking about retirement could face massive tax regret if they don’t act soon. Whether you're already in early retirement or planning to retire soon, you'll learn: ✅ Why the 2025 Roth conversion deadline is a critical tax planning window ✅ How losing ACA subsidies in 2026 could spike your health insurance costs ✅ What triggers Medicare IRMAA penalties—and how to avoid them ✅ How to run your Roth conversion numbers the smart way - all the things you need to be aware of to avoid potential pitfalls ✅ Estate planning, tax brackets, and how strategic Roth conversions can save you six figures 🔥 Don’t miss this Roth conversion opportunity—use it before it disappears. Resources mentioned or for more information: 📊 Department of Treasury, U.S. National Debt: https://fiscaldata.treasury.gov/americas-finance-guide/national-debt/ 📊 Charles Scwaab Conversion Calculator: https://www.schwab.com/ira/ira-calculators/roth-ira-conversion 📊Boldin Conversion Calculator: https://www.boldin.com/retirement/roth-conversion-calculator/ 📊Bloomberg Government: 2025 Tax Policy Crossroads—What Will Happen When the TCJA Expires?: https://about.bgov.com/insights/elections/2025-tax-policy-crossroads-what-will-happen-when-the-tcja-expires/ 📊Thomson Reuters: What to know about TCJA expiration: https://tax.thomsonreuters.com/blog/what-to-know-about-tcja-expiration/ 📊Mariner Wealth Advisors: Early Retirement and Roth Conversions: https://www.marinerwealthadvisors.com/insights/early-retirement-should-you-consider-a-roth-conversion/ 📊Kiplinger: Benefits of Roth IRA Conversions Early in Retirement: https://www.kiplinger.com/retirement/benefits-of-roth-ira-conversions-early-in-retirement 📊Investopedia: How Much Tax Do You Pay on a Roth IRA Conversion?: https://www.investopedia.com/articles/retirement/08/roth-conversion-2010.asp 📊Wells Fargo: Roth IRA Conversion Rules and FAQ: https://www.wellsfargo.com/investing/retirement/ira/roth-ira-conversion/ 📊Money With Katie: The Roth Conversion Ladder: https://moneywithkatie.com/blog/how-to-use-your-401k-in-early-retirement-without-a-10-penalty ❤️ Like, Subscribe, Follow, Share and leave a review if this helped! 💼My Favorite Retirement Planning Tool. If you're serious about planning for early retirement, you've got to check out Boldin.  It's a powerful tool that helps you map out your financial future -- whether you're a DIY planner or just want to stress-test your retirement strategy.  I personally use it and highly recommend!  Try Boldin here: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It's a simple way to support this podcast and the content I create. Thank you! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: Buy me a coffee: https://buymeacoffee.com/mikeupland.com   DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information.  #rothconversion #retireearly #retirementplanning #taxplanning #taxesinretirement #earlyretirement

Are you constantly worried about running out of money in retirement? You’re not alone—and the good news is, the truth might surprise you! In this podcast, I reveal what most people get wrong about retirement spending, how rare it actually is to run out of money, and the real strategies that work—especially if you're retiring early. We’ll break down the 4% rule, portfolio withdrawal strategies, the guardrails approach, and real-world data that shows how most retirees end up with more money than they started with. Whether you're planning for early retirement or already living it, this episode will help you stop worrying and start living! Learn how to make your money last, without the stress. 🔍 Topics covered: ✅ How to stop worrying about running out of money in retirement ✅What the 4% rule really means (and its limitations) ✅The truth about retirement portfolio longevity ✅How guardrails can give you more flexibility and confidence ✅Common mistakes retirees make with money Resources Mentioned: 📊 Michael Kitces article on why most retirees will never spend their entire retirement portfolio: https://www.kitces.com/blog/consumption-gap-in-retirement-why-most-retirees-will-never-spend-down-their-portfolio/ 📊Michael Kitches article regarding implementing retirement income guardrails: https://www.kitces.com/blog/implementing-retirement-income-guardrails-to-facilitate-the-right-spending-raises-and-spending-cuts/ 📊Retirment Planning Tool I Use, Boldin.com: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you!   ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast.   ❤️ Like, Subscribe, Follow, Share and leave a review if this helped! 📺 When you're not on the go, watch the Early Retirement Roadmap YouTube Channel: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This podcast is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #retireearly #earlyretirement #retirementplanning #financialfreedom #financialindependence

Want to retire on $10K a month? This episode shows exactly how much you need saved in 2025 and beyond—factoring in taxes, healthcare, inflation, Social Security, and investment risk. We’ll break down what it really takes to sustain $10,000 in monthly retirement income spending —whether you're aiming for early retirement, following the 4% rule (and why the 4% rule should really be used only as a very rough ballpark estimate), or just want a comfortable, worry-free lifestyle. You’ll also learn how to reduce your savings target without sacrificing your standard of living. You’ll learn: ✅ How much you need to retire with $10K/month in spending ✅ Why withdrawal rate and account types can make or break your plan ✅ How Social Security and other income reduce your savings target ✅ What risks like sequence of returns and inflation really mean ✅ Strategies to optimize taxes and healthcare before Medicare 🔧 Tools Mentioned: Boldin.com: https://go.boldin.com/earlyretirementroadmap Disclosure: This is an affiliate link, which means I may earn a small commission at no extra cost to you. It’s a simple way to support the channel and the content I create. Thank you! Resources: 📊 Morningstar, 3.7% Starting Withdrawal Rate: https://www.morningstar.com/business/insights/research/the-state-of-retirement-income 📊 Morningstar: Re-evaluating the 4% Withdrawal Rule: https://www.morningstar.com/retirement/morningstars-retirement-income-research-reevaluating-4-withdrawal-rule 📊Charles Scwaab – How Many Years of Cash Reserve: https://www.schwab.com/learn/story/market-volatility-retirement-what-if-you-havent-prepared 📊 More about bond tents: https://www.thegoodlifejourney.com/home/bond-tent-early-retirement-strategy? & https://www.kitces.com/blog/managing-portfolio-size-effect-with-bond-tent-in-retirement-red-zone/ ❤️ Like, Subscribe, Follow, Leave a Review, and Share if this helped! ✅ FREE Early Retirement Planning Checklist Whether you're just getting started or refining your plan, this free guide will help you take the next step! Download my free 12-step early retirement planning checklist—a practical, easy-to-follow guide that walks you through everything from calculating your FIRE number to building a tax-efficient withdrawal strategy. 👉 Get your free checklist here: https://payhip.com/b/IBj3q I created this to help others like you pursue financial independence and retire on your own terms and as a thank you to my viewers. Whether you are years away or almost ready, this checklist will help you retire smarter and sooner and is the perfect companion to everything I share on this podcast. 📺When you're not on the go, watch the Early Retirement Roadmap channel on YouTube: https://youtube.com/@EarlyRetirementRoadmap?sub_confirmation=1 🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/ ☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com) DISCLAIMER: This video is for educational purposes only and reflects my personal experience and research. It is not financial, tax, legal, or investment advice. Always consult with qualified professionals before making major retirement or financial decisions. I am not responsible for any loss or damages resulting from reliance on this information. #retireearly #earlyretirement #retirementplanning #financialplanning #retirement