How to Know If You're Really Ready to Retire: A 10-Point Checklist
Retirement—it’s the ultimate goal for so many of us. But how do you know when you’re actually ready? It’s not just about hitting a certain age or financial milestone. True retirement readiness means feeling confident, secure, and prepared for what’s ahead… both financially and emotionally.
Here’s a 10-point checklist to help you find out if you’re truly ready to retire—no second guessing, no cold feet.
✅ 1. You Know Your Monthly Spending Needs
Retirement is less about how much you have and more about how much you need. Have you mapped out your monthly expenses, including fun stuff like travel and hobbies—not just bills?
✅ 2. Your Healthcare Plan is Locked In
Do you know how you’ll cover healthcare before and after Medicare kicks in? Have you budgeted for out-of-pocket costs, long-term care, and unexpected health events?
✅ 3. You Have a Reliable Income Plan
Will your income come from multiple sources—Social Security, pensions, investments, annuities? Have you created a withdrawal strategy that minimizes taxes and maximizes longevity?
✅ 4. Your Debts Are Under Control
Carrying a mortgage or high-interest debt into retirement can put stress on your savings. Are you debt-free, or is your plan flexible enough to handle remaining balances?
✅ 5. You’ve Done a Tax Projection
Have you looked at your projected tax situation post-retirement? Understanding tax brackets, Roth conversions, and RMDs can help you avoid costly surprises.
✅ 6. You’ve Run the Numbers (With a Professional)
Have you worked with a financial planner to test your plan against real-world scenarios—market downturns, inflation, healthcare spikes? A Monte Carlo simulation can give you confidence.
✅ 7. Your Estate Plan Is in Order
Wills, trusts, powers of attorney—are they updated? Do your beneficiaries reflect your current wishes?
✅ 8. You Have a Purpose or Plan for Your Time
Retirement isn’t a forever vacation. Do you know what you’ll do with your time? Volunteering, hobbies, travel, part-time work?
✅ 9. You’re Emotionally Ready to Leave Work
Are you retiring from something or to something? Big difference. Are you mentally prepared to unplug from your career?
✅ 10. You Have a Go-To Financial Team
Do you have someone to call when life changes or questions pop up? Retirement isn’t a one-and-done decision—it’s an ongoing process. We’d love to be on your team! Give us a call and let’s check off your list! 813.254.9500.
