I retired at 55. How did I know I had enough to retire early? I looked at whether our retirement plan could pay for the life we wanted, bridge the years before Medicare, and hold up in a bad market.

I started with the retirement we actually wanted, including travel and the things we enjoy—not a budget stripped down to the bills. Then I had to work out where our spending money would come from in the early years. I explain why the Rule of 55 wasn't my bridge, how our taxable brokerage account helped, and why the accounts you draw from can affect ACA health insurance subsidies.

I also share why I built a cash runway of about four years, what an expensive A/C repair taught me in my first year of retirement, and how I decided whether working one more year would meaningfully improve our plan.

There was no magic account balance that made the future certain. I needed a plan that could support the life we wanted and give us choices when things didn't go as expected.

✅ Free resources available on my Patreon:

All of my Roadmap tools, checklists, worksheets, downloads, and resources are now free to members who join for free. That includes things like my ACA MAGI Estimator, retirement readiness scorecard, cash runway worksheet, 10 Ways to lower your ACA premiums ebook, Treasury bill ladder guide, CD ladder guide, quarterly retirement review worksheet, and more. To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space.

💼 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!

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

I retired at 55, and I’m thinking about the retirement regrets I want to avoid by 80. These 8 early retirement lessons cover spending, taxes, cash, health, travel, marriage, and changing the plan as life changes.

I could make sound financial decisions and still regret how my wife and I used our years. After hearing about regrets people shared in their 80s, I asked myself which ones could become mine—and what I can do about them now.

In this episode, I talk about eight regrets I’m working to avoid:

1. Saving the best years for later
2. Making a permanent move too soon
3. Planning taxes one year at a time
4. Following someone else’s retirement plan
5. Confusing cash with complete safety
6. Taking health for granted
7. Assuming my wife and I want the same retirement
8. Treating the retirement plan as finished

Some of these choices involve money. Others involve how we spend our time, protect our health, and build a retirement that works for both of us. I’m sharing my approach as someone living through early retirement, not a plan for everyone to copy.

✅ Free resources available on my Patreon:

All of my Roadmap tools, checklists, worksheets, downloads, and resources are now free to members who join for free. That includes things like my ACA MAGI Estimator, retirement readiness scorecard, cash runway worksheet, 10 Ways to lower your ACA premiums ebook, Treasury bill ladder guide, CD ladder guide, quarterly retirement review worksheet, and more. To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space.

💼 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!

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

Gen X was told to work hard, be loyal, save for retirement, and follow the rules. But somewhere along the way, the rules changed. In this interview, I talk with author Mark Ross about work, retirement, time, success, and the Gen X experience.

Mark is the author of Generation X and the Life Nobody Explained, a book that really resonated with me because so much of it reflects what I’ve experienced — and what I’ve been talking about recently on this channel.

We discuss how the relationship between employees and employers changed, why so many Gen Xers stopped trusting the old career model, what happened to retirement parties, why the 401(k) shifted so much responsibility onto individuals, how technology consumed more of our time, and why hobbies, craftsmanship, and even our definition of success changed along the way. We also talk about what comes next.

For many of us in Generation X, the second half of life is becoming less about chasing titles, promotions, and money — and more about freedom, time, health, curiosity, relationships, and deciding what we actually want the rest of our lives to look like. In this conversation, we cover: • Why Gen X entered adulthood with one “map” and ended up living by another • How employment shifted from a relationship to a transaction • Why work began consuming more of our time — even outside work • What happened to hobbies and unstructured time • Why retirement became less certain • How the 401(k) changed the responsibility for retirement • Why Gen X is redefining success • Why the second half of life may be the most important chapter yet 📘 Click here for Mark Ross’s book: Generation X and the Life Nobody Explained Disclosure: This is an affiliate link - I earn a small commission if you purchase the kindle or paperback version of Mark's book. This link doesn’t cost you anything extra and helps to support the content I create. Thank you!

✅ Free resources available on my Patreon:

All of my Roadmap tools, checklists, worksheets, downloads, and resources are now free to members who join for free. That includes things like my ACA MAGI Estimator, retirement readiness scorecard, cash runway worksheet, 10 Ways to lower your ACA premiums ebook, Treasury bill ladder guide, CD ladder guide, quarterly retirement review worksheet, and more. To get the free downloads, go to my Patreon here: https://www.patreon.com/cw/earlyretirementroadmap

Click **Join for Free**, then go to the **Tools** collection. You can download any of the free tools and resources there.

If you’d like to go a step further, the $5/month Roadmap Member tier includes early access to podcast episodes, ad-free podcast episodes, and access to the private Roadmap Member community discussion space.

💼 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!

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