5 Questions to Know If You’re Really Ready to Retire
When I sit down with people planning for retirement, the focus is almost always on the numbers. Have I saved enough? What’s my withdrawal rate? When should I claim Social Security?
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.
