October 13, 2025

7 “Assets” Rich Retirees Avoid

8 minutes

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.

...more

View all episodes

By Mike Upland

4.8

66 ratings