Am I Ready for Retirement? 5 Questions to Ask Yourself Before You Retire

Retire Smarter: 5 Questions to Ask Yourself Before You Retire

 

Retirement marks the beginning of a new chapter—one filled with freedom, opportunities, and important decisions. But before you leave the working world behind, it’s critical to ask: Am I truly prepared?

 

Here are five key questions to help you evaluate your readiness and build a confident plan for the years ahead:

1. Do I Have a Sustainable Income Plan?

 

Replacing your paycheck requires more than just savings—it requires strategy. Whether your income will come from Social Security, pensions, investment withdrawals, or rental income, it's vital to know how much you can safely draw each year.

 

Ask yourself:

  • Do I know how much income I’ll need monthly?
  • Have I accounted for inflation and rising costs over time?
  • Have I stress-tested my withdrawal strategy in down markets?
2. Have I Accounted for Healthcare and Long-Term Care?

 

Even with Medicare, healthcare costs in retirement can be surprisingly high—especially if long-term care becomes necessary. Planning for these expenses helps prevent your savings from being derailed.

 

Ask yourself:

  • Do I understand what Medicare covers—and what it doesn’t?
  • Should I purchase a supplemental or long-term care policy?
  • Have I budgeted for out-of-pocket medical costs?
3. Am I Managing My Debt and Expenses Wisely?

 

The less debt you carry into retirement, the more freedom you’ll have with your income. At the same time, your budget may look different without work-related expenses—but new costs like travel or home repairs may increase.

 

Ask yourself:

  • Have I paid down high-interest debt, like credit cards or personal loans?
  • Will I carry a mortgage in retirement—and am I comfortable with that?
  • Have I built a realistic retirement budget?
4. Do I Have a Clear Investment Strategy?

 

Your investment strategy shouldn’t stop at retirement—it should evolve. Withdrawing from the right accounts at the right time can help reduce taxes and keep your portfolio on track for decades.

 

Ask yourself:

  • Is my portfolio appropriately diversified for my age and goals?
  • Do I understand the tax implications of my withdrawals?
  • Am I balancing growth and preservation effectively?
5. What Will Give My Life Purpose in Retirement?

 

Financial preparation is critical, but so is emotional readiness. Without the structure of work, retirees often need to redefine their purpose, routine, and social life.

 

Ask yourself:

  • What will bring me meaning, purpose, and joy in retirement?
  • How will I stay mentally, physically, and socially engaged?
  • Do I have hobbies, passions, or causes I want to explore?

Final Thoughts

 

If you’re approaching retirement and can’t confidently answer these five questions, you’re not alone. The transition to retirement involves more than numbers—it’s about aligning your finances with the life you want to live.

 

Whether you’re a few months or a few years away, it’s never too early—or too late—to put a thoughtful plan in place. A trusted financial advisor can help guide you through each step, so you can retire not just comfortably, but confidently.