I Retired at 55: 7 Early Retirement Mistakes I Missed

Early retirement planning tips from someone who actually did it: I retired at 55, and in this episode, I share 7 early retirement mistakes I missed so you can retire early with fewer surprises and avoid costly retirement planning mistakes.

If you’re searching for early retirement planning tips, retirement planning advice, and early retirement mistakes to avoid, this video walks through what caught me off guard after retiring at 55. I cover how a bad day at work can push you toward early retirement before the plan is ready, why you should not assume you can easily go back to work, how a spouse can be on a different retirement timeline, why spending in retirement can feel harder than expected, how big surprise expenses still sting, why you should test-drive retirement before you quit, and why retirement planning does not end once you retire.

I also share my personal experience with retiring at 55, adjusting to life after full-time work, shifting from saving to spending, and dealing with the real-world side of early retirement planning. That includes health insurance planning, withdrawal strategy, modified adjusted gross income management, Roth conversions, and long-term tax planning.

✅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. Here is the link to my Patreon: https://www.patreon.com/cw/earlyretirementroadmap

💼 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/

☕ Support: [Buy me a coffee](https://buymeacoffee.com/mikeupland.com)

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.

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(73)

I'm 57 Now. Here's What I'd Tell My 40-Year-Old Self.

After retiring at 55, I discovered that early retirement is about more than money. Here are the retirement lessons I wish I knew at 40 about time, health, work, freedom, and family. When I was 40, I t...

17 Aug 23min

I Retired at 55—5 Problems My 401(k) Couldn’t Solve

I retired at 55, and I learned that a large 401(k) alone doesn’t solve every early retirement problem—especially access, ACA health insurance, taxes, and market downturns. In this episode, I walk thro...

10 Aug 17min

I Retired at 55 — Here’s the Risk Nobody Warns You About

The big question that's always asked when it comes to retirement planning is do you have enough money? But the risk nobody warns you about is retiring too late. After retiring at 55, I’ve learned that...

3 Aug 11min

I Retired at 55. My Retirement Plan Is Intentionally Dumb.

I retired at 55 with an intentionally dumb retirement plan—simple retirement planning built around low-cost index funds, cash reserves, flexible spending, and fewer moving parts. In this episode, I sh...

27 Jul 15min

I Retired at 55—6 Signs Work Was Taking Too Much From Me

Working too much can quietly drain your time, energy, health, and relationships. After retiring at 55, I saw how burnout, work-life balance, and early retirement are more connected than I realized. In...

20 Jul 17min

I’m 57. I Retired at 55. Why Am I Still Afraid to Spend Money?

Retirement spending, early retirement, and the fear of spending money can feel strange after decades of saving. I retired at 55, and even with a solid plan, spending from the pile was harder than I ex...

13 Jul 12min

I Retired at 55: My 7 Budget Rules That Survived Real Life

Retirement budget rules matter even more when you retire early. I retired at 55, and in this episode I’m sharing the 7 budget rules that helped my retirement plan survive real life. Before I retired, ...

6 Jul 17min

I Retired at 55: Don't Let a Calculator Keep You Working

Retirement calculators, Monte Carlo simulations, and probability of success can be useful—but they can also keep you working one more year. I retired at 55, and here’s what I think calculators often m...

29 Jun 16min