Are You Really Ready to Retire? 7 Key Questions to Ask Yourself First

 Thinking about retirement soon? Discover 7 essential questions every pre-retiree should ask to feel more confident about the next chapter — financially and emotionally.

 You’ve worked hard, saved diligently, and retirement is finally in sight. But before you celebrate your final clock-out, there’s one important question to answer:

Are you really ready to retire?

Retirement isn’t just about reaching a certain age or savings milestone — it’s about knowing your entire lifestyle is supported, your identity has a place to land, and your finances can weather what’s ahead.

Here are 7 essential questions to help you find out where you stand:

1. Do You Know Your Retirement Number?

Have you calculated how much you actually need to live comfortably — not just in year one, but for 20–30+ years? This includes monthly expenses, healthcare, inflation, and a buffer for fun.

2. Have You Accounted for Market Volatility?

Retiring into a down market can seriously impact your nest egg. Do you have a strategy to manage withdrawals without selling at a loss?

3. What Will You Do About Health Insurance?

Medicare doesn't cover everything. Do you understand the out-of-pocket costs, supplemental plans, and long-term care options you may need?

4. Have You Optimized Your Social Security?

The age you claim benefits can impact your monthly income for life. Have you run the numbers on when to file?

5. Are You Tax-Savvy With Your Withdrawals?

Do you know the best order to tap your accounts — 401(k), Roth IRA, brokerage — to minimize taxes and avoid penalties?

6. Do You Have a Purpose Beyond Work?

Retirement isn’t just about finances. Have you thought about how you’ll spend your time, find fulfillment, and stay connected?

7. Is Your Estate Plan in Place?

If something unexpected happened, would your family know your wishes — and be protected financially?

Conclusion:
Retirement is a huge transition — but the more questions you ask now, the fewer surprises you’ll face later.

👉 Grab our free Retirement Readiness Checklist to assess where you stand and uncover the gaps before you make the leap.