March 11, 2026

Retire Now If You Can Answer Yes to These 6 Questions

18 minutes

Early retirement + retirement planning made simple: Can you retire now?

In this episode, I share 6 questions to test your financial independence and retirement readiness—before you make the leap. If you can honestly answer YES to all six, you may be closer to retirement than you think:

The 6-question retirement test:

1. Are you postponing the life you actually want?

2. Is your job taking a real toll on your health?

3. Have you outgrown this stage of your career?

4. Do you want more time with the people you love—while you can still enjoy it?

5. Do you know what you’re retiring to?

6. Have you run the numbers well enough to trust the decision?

✅ Want the companion tool for this video? I created a Retirement Readiness Scorecard (based on these 6 questions) so you can work through them for yourself and see where you stand.

🎯 Get it inside my Patreon Tools Library (I usually make at least one tool for every major video/podcast topic).

⭐ Join my Patreon (3 levels)

• Tools Library access (including this Scorecard)

• Tools + ad-free, early-access podcast episodes

• Top tier: ask me your early retirement questions directly

👉 Patreon link: https://www.patreon.com/cw/earlyretirementroadmap

✅Get these Free Resources available too 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 video! 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 video 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.

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By Mike Upland

99 ratings