Retiring soon? In this episode, I cover the biggest retirement planning mistake people make before retirement and the 7 things to figure out now, including spending, taxes, health insurance before Medicare, withdrawal strategy, and cash runway.

A lot of people do a good job saving for retirement, but they wait too long to plan the actual transition into retirement.

That’s the mistake.

In this episode, I walk through 7 key areas to get clear on before you retire so you’re not scrambling late in the game:

What retirement will actually cost
Where your retirement income will come from
Your withdrawal strategy
Health insurance before Medicare
Major financial loose ends to clean up
The mental side of retirement
Why a cash runway matters so much

If you’re planning for retirement or early retirement, this episode will help you think through the practical side of retirement planning, including retirement spending, taxes, Modified Adjusted Gross Income (MAGI), Affordable Care Act health insurance, and sequence of returns risk.

✅Free Resources available on my Patreon!:

📊Free MAGI calculator Excel template

📊Free 12-Step Early Retirement Planning Checklist

📊Free eBook: ACA Premium Shock Fix, 10 Ways to Pay Less for Marketplace Coverage All Year Long

👉To get these free downloads, go to my Patreon, click Join for Free, then click on the Tools collection, and you can download any of them from there. While you're there, check out my different membership levels too! There is sure to be a level that fits your needs and budget.Join any paid tier level to get access to my entire tools collection, including my Early Retirement 5 Numbers Excel Worksheet, Cash Runway Calculator Worksheet, Treasury Bill and CD Ladder Guides I mentioned in this episode. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

📊ACA Cost Estimator Link mentioned in this episode: https://www.healthcare.gov/see-plans/#/

📊2025 FPL Tables - ACA Uses This for 2026: https://aspe.hhs.gov/sites/default/files/documents/dd73d4f00d8a819d10b2fdb70d254f7b/detailed-guidelines-2025.pdf

🎧Listen next to my recent podcast episode The Cash Runway Plan: Build It, Store It, Refill It mentioned it in this episode & the episode titled ACA MAGI: How to Calculate & Manage It for Big Savings!

💼 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!

🌐 Visit my website for all my media, including my blog or to contact me about sponsorship or other business opportunities: https://mikeupland.com/

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DISCLAIMER: This episode 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.

Retiring Soon? Don’t Make this Mistake