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Early Retirement Roadmap

Early Retirement Roadmap

Written by: Mike Upland
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About this listen

Welcome to the Early Retirement Roadmap podcast, your audio guide to preparing for and thriving in early retirement! If you’re dreaming of retiring early but feeling overwhelmed about where to start, or if you’re already retired and looking to make the most of your freedom, you’re in the right place. I’m your host Mike Upland, and I successfully retired at 55. Through this podcast, I share my personal early retirement journey—the victories, the challenges, and all the essential lessons I’ve learned along the way. Each episode delivers practical strategies and real-world insights on crucial topics like financial planning, developing the right mindset, and finding purpose in retirement. You’ll hear candid discussions about the realities of early retirement, actionable tips for building wealth, and inspiring stories to help you navigate your own path to early retirement. Whether you’re just starting to explore early retirement or fine-tuning your existing plans, this podcast provides the roadmap you need to build a financially secure and fulfilling post-career life. For visual guides and additional content, be sure to check out the Early Retirement Roadmap YouTube channel, where I share complementary videos and resources to support your early retirement journey. Your early retirement journey starts here—subscribe now to ensure you never miss an episode!Copyright 2025 All rights reserved. Economics Personal Finance Self-Help Success
Episodes
  • ACA Premium Shock: 10 Ways to Pay Less All Year
    Jan 12 2026

    ACA premium shock for 2026? If your Marketplace/Obamacare health insurance premium jumped, this video shows 10 practical ways to pay less all year by controlling MAGI (modified adjusted gross income) and avoiding costly income mistakes.

    Health insurance is the #1 “elephant in the room” for early retirement. With enhanced ACA subsidies ending after 2025, many early retirees are seeing big premium increases — but the ACA is still income-based, not asset-based, which means you may have more control than you think.

    In this episode, I break down: ✅ Why many early retirees still choose ACA/Marketplace plans ✅ How the 400% Federal Poverty Level (FPL) line affects premium tax credits ✅ Why 250% FPL matters for cost-sharing reductions (Silver plans) ✅ 10 specific levers you can use to manage MAGI and pay less — including capital gains control, Roth strategy, cash runway, HSAs, dividend/interest “silent MAGI,” Roth conversion timing, and updating your income during the year

    Important: Even after you enroll, you can update your Marketplace income estimate during the year — this can help prevent overpaying (or owing money back at tax time).

    ❤️ 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 in this episode: - Click here for 2025 FPL Tables - ACA Uses the 2025 tables for 2026. - Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans. - Click here for the free early retirement checklist, 12 Must-Do Steps to Retire Sonner and Smarter

    🎧 My Podcast episodes mentioned in this episode to listen to next: - Season 1, Episode 4: Health Insurance Options for Early Retirement: What You NEED to Know - goes over the pros and cons of health insurance options for early retirement, including and beyond the ACA - Season 2, Episode 14: ACA MAGI: How to Calculate & Manage It for Big Savings! - goes over exactly how to calculate your Modified Adjusted Gross Income (MAGI)

    🌐 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.

    Show More Show Less
    19 mins
  • 2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)
    Jan 5 2026

    2026 401(k) and IRA contribution limits are rising from 2025—but maxing out can backfire if you’re planning early retirement. In this episode I break down 3 rules to fund the right accounts in the right order.

    If you’re aiming to retire before 59½, the “max everything” advice can accidentally:

    • lock up money when you need flexibility
    • increase taxes later (required distributions and tax brackets)
    • make health insurance more expensive by pushing up income (Affordable Care Act subsidies)

    In this episode you’ll learn:

    1. When maxing your 401(k) does make sense (and when it doesn’t)
    2. The best “order of operations” for early retirees (401(k), IRA, Roth, Health Savings Account, taxable brokerage)
    3. How to balance tax savings today vs. flexibility and taxes later

    ❤️ Depending on the platform you're listening on, please Like, Subscribe, Follow & Share, and leave a positive review if you found this episode helpful!

    👉Additional Info beyond this episode: If you retire before 59½ and don’t have enough in a taxable brokerage “bridge,” there is another tool called IRS Rule 72(t) (also called SEPP — Substantially Equal Periodic Payments). It can be a legit way to access IRA money early without the 10% penalty, but it comes with some important strings attached (it’s rigid, and mistakes can be costly). Fore more information on this, listen to my podcast episode devoted to this, titled How to Tap Your IRA or 401(k) Early —NO IRS PENALTY! | Rule 72(t) Explained, it's Season 2, Episode 9.

    👉 Free Resource 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

    📺 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.

    Show More Show Less
    10 mins
  • Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)
    Dec 15 2025

    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.

    Show More Show Less
    12 mins
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