
Sign up to save your podcasts
Or


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 share the seven parts of my early retirement plan that I deliberately keep simple. That includes how I invest, why I use a small number of investments with clear jobs, how I avoid trying to predict the market, and why I treat retirement calculators and Monte Carlo simulations as tools—not guarantees.
I also explain why I don’t try to optimize every tax year, how I built flexibility into my retirement spending plan, and why every retirement strategy should pass the “spouse test.” A retirement plan shouldn’t require perfect forecasts, constant monitoring, or dozens of complicated decisions to keep working.
My goal is not to have the smartest-looking retirement plan. It is to have a resilient retirement plan that is easy to understand, hard to break, and flexible enough to handle market downturns, unexpected expenses, changing tax rules, and real life.
In this episode, we’ll cover:
✅ 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.
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.
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.
By Mike Upland5
99 ratings
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 share the seven parts of my early retirement plan that I deliberately keep simple. That includes how I invest, why I use a small number of investments with clear jobs, how I avoid trying to predict the market, and why I treat retirement calculators and Monte Carlo simulations as tools—not guarantees.
I also explain why I don’t try to optimize every tax year, how I built flexibility into my retirement spending plan, and why every retirement strategy should pass the “spouse test.” A retirement plan shouldn’t require perfect forecasts, constant monitoring, or dozens of complicated decisions to keep working.
My goal is not to have the smartest-looking retirement plan. It is to have a resilient retirement plan that is easy to understand, hard to break, and flexible enough to handle market downturns, unexpected expenses, changing tax rules, and real life.
In this episode, we’ll cover:
✅ 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.
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.
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.

444 Listeners

810 Listeners

1,333 Listeners

455 Listeners

536 Listeners

750 Listeners

548 Listeners

700 Listeners

582 Listeners

833 Listeners

204 Listeners

584 Listeners

1,069 Listeners

101 Listeners

19 Listeners