10 Overlooked Signs You’re Not Ready to Retire, Ep 191

Many people dream of retiring as soon as possible, but rarely stop to ask if they’re truly ready. It’s easy to assume you’ll figure things out when you get there, but this episode challenges that thinking by revealing 10 overlooked signs you may not be ready to retire yet. Even if you’re eager to leave the 9-to-5 behind, there are critical financial, emotional, and lifestyle factors you might not have fully considered, ones that can derail your dream if ignored.

We’ll explore issues like carrying too much debt, lacking a solid income plan, underestimating healthcare costs, or not having a clear picture of what you’ll actually do all day. For many, these topics can be uncomfortable because they reveal blind spots that feel hard to fix. But in walking through them one by one, we highlight how acknowledging these signs isn’t about delaying your freedom, it’s about ensuring you can sustain it joyfully and securely. You’ll discover practical ways to reduce financial risks, anticipate new expenses, and plan the life you actually want once work ends.

By the end of this episode, you’ll not only recognize the hidden gaps in your own plan but also see the value of taking action now. Whether that means rethinking your budget, getting strategic about Social Security, or simply having more honest conversations with your partner, you’ll leave with a clearer idea of how to transition from working years to retirement with confidence. Instead of winging it, you’ll be ready to retire on purpose, with eyes wide open.

You will want to hear this episode if you are interested in…

(00:00) Intro.
(00:27) YouTube channel and free resources plug.
(03:13) 10 signs overview and Sign 1: Carrying significant debt.
(05:07) Sign 2: No retirement income plan.
(06:17) Signs 3 and 4: Missing budget and healthcare costs.
(09:43) Signs 5 – 7: Social Security, long-term care, RMD planning.
(13:05) Signs 8 – 10: Emotional readiness, spousal coordination, investment repositioning.

Why retirement isn’t just about walking away from work

Retirement sounds simple: stop working and enjoy life. But I’ve seen too many people underestimate what that really takes. Debt, healthcare costs, and unplanned expenses can eat away at your security. I want listeners to see that retirement isn’t just an end to a career, it’s the start of a new stage that deserves real planning.

If you haven’t taken a hard look at your budget, your income streams, or your strategy for things like Social Security, it’s time to be honest about whether you’re truly ready.

Don’t let hidden financial traps ruin your retirement dreams

One of the biggest surprises for people nearing retirement is realizing their savings and investments might not be positioned for what comes next. It’s not enough to have a big balance; you need a plan for turning it into reliable, sustainable income. I see folks forget about taxes, required distributions, or rising healthcare costs. These aren’t abstract problems; they’re predictable challenges that can be addressed with the right strategy.

It’s also important to think about how your risk tolerance changes once you’re retired. You may need to pivot from chasing growth to prioritizing steady income and lower volatility. The more proactive you are now, the fewer unpleasant surprises you’ll face down the road. It’s about making sure your money works for you when you need it most, giving you the freedom to enjoy retirement with confidence.

Plan beyond money: create a clear vision for life in retirement

Financial readiness is just part of the equation. I want listeners to consider what they’ll actually do each day once work stops. Many don’t think about purpose, hobbies, or even coordinating plans with a partner until it becomes a problem. Retirement isn’t just about freedom from work; it’s about moving toward something meaningful.

Whether it’s volunteering, travel, part-time work, or family time, I encourage everyone to paint that picture in detail before making the leap. That clarity can mean the difference between a stagnant, frustrating retirement and one that truly fulfills you.