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:

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 this episode titles I mentioned in this podcast and some others that are related/may be of interest: 

💼 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)

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:

Quick checklist to get clarity:

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: 

💼 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)

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:

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: 

💼 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)

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):

Plan B (if enhanced subsidies continue):

📊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:

🔔 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

🎥 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:

My 3-step Keep, Sell, or Swap framework:

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!

👉 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!

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:

🔗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!

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:

🔗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!

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:

🔗 Click here for the free MAGI Calculator Template (Microsoft Excel download). Use it to estimate your MAGI for ACA plans.

🎧 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!

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:

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:

❤️ 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