Early Retirement Roadmap

2026 401(k) & IRA Limits Are Up—But Maxing Out Can Backfire (3 Rules)

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:
When maxing your 401(k) does make sense (and when it doesn’t)
The best “order of operations” for early retirees (401(k), IRA, Roth, Health Savings Account, taxable brokerage)
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.
 
 

Monthly Dividend ETFs: The Paycheck Illusion (3 Tests to Avoid a Costly Mistake)

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.

6 Levels of Retirement Wealth – Which Level Are You?

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 Lazy Retirement: My 9 Habits of Thriving Retirees

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.
 
 
 
 

My Lazy Retirement Investing Plan

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 this episode titles I mentioned in this podcast and some others that are related/may be of interest: 
How a Mutual Index Fund Cost Me $17K in Taxes (And How to Avoid This Mistake)
🚨No Subsidies in 2026? Plan A vs Plan B (DO THIS)
How I Retired at 55: Do These 5 Things
ACA MAGI: How to Calculate & Manage It for Big Savings!
Roth Conversions or ACA Subsidies? The Early Retirement Dilemma No One Talks About
Will ACA Subsidies Disappear After 2025? What You NEED to Know!
How Early Retirees Can Pay WAY Less for Health Insurance!
The $12,900 Health Insurance Loophole for Early Retirees!
Health Insurance Options for Early Retirement: What You NEED to Know
💼 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.

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.
 

7 Signs You Should Retire Earlier Than You Think

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.
 
 

🚨No Subsidies in 2026? Plan A vs Plan B (DO THIS)

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 ChecklistWhether 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/IBj3qI 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.

5 Things to Sell BEFORE You Retire

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.
 

7 “Assets” Rich Retirees Avoid

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.