Don’t get me wrong—those are critical questions. But retirement readiness goes beyond spreadsheets and simulations. It’s not just about whether you can retire it’s about why, when, and how you want to live the next phase of your life.

In this article, I want to shift the conversation and ask you five essential questions that go deeper than financial figures. These questions are designed to help you find the right balance between security and fulfillment.

1. Am I Trading Time for Money I May Never Use?

One of the most sobering moments in my career came from a client who worked tirelessly into his late 60s. He was driven by financial perfection he wanted to hit one more milestone, boost his portfolio just a little more. He finally retired… and passed away shortly afterward.

That experience shook me. It’s a reminder that time is a nonrenewable resource. Working longer can strengthen your retirement finances but at what cost? If you’re delaying retirement in pursuit of a few more percentage points, ask yourself: Am I sacrificing experiences I may never get back?

2. What Is the Cost of Working Longer on My Health?

By the time most people reach their early 60s, they’ve been through decades of stress, deadlines, raising kids, and juggling responsibilities. And it shows. Studies link prolonged work stress to higher risks of depression, heart disease, and stroke.

You can plan for a long retirement, but don’t forget to plan for a healthy one too. The longer you work, the more you may be chipping away at the healthiest years you’ve got left. I always ask clients: Are you extending your financial runway at the expense of your health span?

3. How Much Time Do I Really Have Left with the People I Care About?

Retirement isn’t just about not working it’s about living. And a big part of living is being with the people who matter most. Yet for many of us, work steals the bulk of our waking hours. Long commutes, late-night emails, weekend shifts—they all add up to lost moments.

Think about your aging parents, your grandkids, your friends who live across the country. How many more trips, birthdays, or holidays will you get with them? Retirement gives you back time but only if you take it.

4. Am I Planning for a Healthy Retirement Or Just a Long One?

There’s a big difference between life span and health span. Life span is how long you live. Health span is how long you stay energetic, active, and vibrant.

The first five years of retirement are often the best years to do the things you’ve always dreamed of: travel, take up new hobbies, spend quality time with grandkids. But if you wait too long, your body may not keep up with your bucket list. Don’t plan your retirement to begin after your best years plan it to include them.

5. Am I Letting Fear Delay a Financially Feasible Retirement?

I’ve seen it more times than I can count people who are financially ready to retire but just can’t bring themselves to do it. “Just one more year,” they say. But one becomes two, then five.

Yes, you need to be financially prepared. But sometimes we confuse preparation with perfection. If your plan is solid, your debts are low, and your income streams are in place, don’t let fear rob you of the time you’ve earned. The goal is not to die with the most money it’s to live with the most meaning.

Final Thoughts: Balance Is the Real Goal

If you’ve already asked yourself the classic financial questions what’s my savings target, what’s my withdrawal rate, when to take Social Security great. But now it’s time to ask yourself these five deeper questions.

Because the truth is, retirement readiness isn’t just about having enough money. It’s about having enough life left to enjoy it.

You should always consult a financial, tax, or legal professional familiar about your unique circumstances before making any financial decisions. This material is intended for educational purposes only. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Any mentioned rates of return are historical or hypothetical in nature and are not a guarantee of future returns.

Past performance does not guarantee future performance. Future returns may be lower or higher. Investments involve risk. Investment values will fluctuate with market conditions, and security positions, when sold, may be worth less or more than their original cost.

The post 5 Questions to Know If You’re Really Ready to Retire appeared first on ROI TV.

The Importance of the Last Five Years of Working

The final years of your working career can be surprisingly powerful when it comes to retirement preparation. Thanks to peak earnings, fewer financial responsibilities, and the compounding effect on your investments, this is when you can make significant strides toward your retirement goals.

With compound interest reaching its peak, your portfolio could even double in value in these last few years, setting you up for a more secure retirement. Use this time to ramp up your contributions, if possible, and take advantage of any employer matching, catch-up contributions, or other opportunities to maximize your retirement accounts.

Harnessing the Power of Compound Interest

In retirement planning, compound interest is a powerful force—but it takes time to reach its full potential. The magic of compounding doesn’t typically yield the biggest rewards until the later years. For instance, Warren Buffett’s net worth growth surged after age 56, showing how compounding accelerates as you approach retirement.

These last five years provide the ultimate payoff for years of consistent investing. Each additional dollar saved now has the potential to generate even more returns over time, allowing your retirement portfolio to grow substantially right before you need it most.

Estimating Retirement Expenses and Financial Needs

One of the most important steps in retirement planning is having a clear picture of what your expenses will look like. In these final years, start refining your estimates by evaluating your expected spending on essentials, travel, and leisure activities. This period offers a chance to assess whether your retirement income will align with your anticipated expenses and make adjustments as necessary.

Take time to review costs related to lifestyle choices—such as downsizing, relocating, or increasing travel—and be realistic about potential changes in spending habits. Accurate cost estimation provides clarity, reducing financial stress and giving you confidence that you’ll have enough to enjoy your retirement.

Paying for Big Expenses Before Retirement

The last years before retirement are an excellent time to address major expenses. With a steady income, now is your chance to tackle big costs—whether it’s home repairs, a new car, or even debt repayment. Paying for these expenses while you’re still working can reduce your financial burden during retirement, preserving more of your retirement savings for daily needs and lifestyle goals.

By handling these major expenses now, you set yourself up for a smoother, less stressful retirement. Financially and emotionally, you’ll be better prepared, knowing you’ve already taken care of potential financial drains.

Taking Care of Medical Procedures

Medical needs often increase with age, so it’s wise to use your employer’s health insurance to cover necessary procedures while you’re still working. Health insurance coverage through an employer is often more comprehensive and less costly than options available after retirement, such as Medicare or private insurance.

Consider scheduling check-ups, surgeries, or preventative care during these last working years. Not only will this help address any health concerns, but it can also alleviate some of the financial strain that unexpected medical expenses might otherwise place on your retirement funds.

Envisioning and Planning Your Retirement Lifestyle

The final years before retirement are also an ideal time to dream about the life you want to lead. Retirement is more than financial security; it’s a chance to redefine yourself, pursue passions, and build a lifestyle that brings joy and purpose.

Take time to envision the experiences and activities that will make retirement fulfilling for you. Whether you’re dreaming of travel, hobbies, volunteering, or simply spending more time with loved ones, start outlining these goals and creating a plan to achieve them. A clear vision of your ideal retirement will help guide both your financial planning and personal decisions, ensuring that you’re prepared for an enjoyable and meaningful post-career life.

Final Thoughts

The last five years before retirement are a golden opportunity to make financial and emotional preparations that will set the tone for your retirement years. By maximizing your investments, understanding future expenses, tackling major costs, and planning your ideal lifestyle, you’ll set yourself up for a retirement that is both secure and deeply fulfilling. Embrace these final working years as a chance to build the foundation for the retirement of your dreams.

You should always consult a financial, tax, or legal professional familiar about your unique circumstances before making any financial decisions. This material is intended for educational purposes only. Nothing in this material constitutes a solicitation for the sale or purchase of any securities. Any mentioned rates of return are historical or hypothetical in nature and are not a guarantee of future returns.

Past performance does not guarantee future performance. Future returns may be lower or higher. Investments involve risk. Investment values will fluctuate with market conditions, and security positions, when sold, may be worth less or more than their original cost.

The post The Final Five Years: Key Steps to Financial and Emotional Preparation for Retirement appeared first on ROI TV.