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5 Signs You May Be Ready to Retire

Written by Tom MooreJune 16, 2026

3-MIN READ

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5 Signs You May Be Ready to Retire

Reviewed by Tom MooreJune 16, 2026

3-MIN READ

Share on FacebookShare on InstagramShare on LinkedInShare on YouTube

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One of the questions I hear most often is, “How do I know if I’m really ready to retire?”
While everyone’s situation is different, there are a handful of indicators I look for when helping clients determine whether retirement is financially realistic and sustainable. Retirement isn’t just about reaching a certain age, it’s about having confidence that your income, expenses, and overall plan are aligned.
Here are five questions to ask yourself that may help you decide if you’re ready for retirement.

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1. Does your Social Security plus 4% of portfolio cover your living expenses?

When I evaluate retirement readiness, I start by looking at income.
For many retirees, Social Security provides an important foundation, but it’s rarely the whole picture. I want to see that Social Security, combined with withdrawals from investment accounts and other income sources, can comfortably cover your expected living expenses.
The goal isn’t simply having a large portfolio. The goal is knowing that your assets can generate the income you need to support the lifestyle you want.

2. Are your major financial obligations behind you?

Retirement tends to be much easier when you’ve already tackled the big-ticket expenses.
Whether that’s paying off a mortgage, completing a major home renovation, or eliminating other significant debt, entering retirement with fewer financial obligations gives you more flexibility and control over your cash flow.
The fewer large expenses you’re carrying into retirement, the more freedom you’ll have to enjoy it.

3. Is your Health Insurance secure?

Healthcare is one of the most important, and often overlooked, parts of retirement planning.
Before retiring, I encourage clients to understand exactly where their health coverage will come from, whether that’s Medicare, a supplemental Medicare plan, or an individual insurance policy.
Having a clear understanding of premiums, coverage, and potential out-of-pocket expenses can help you avoid surprises and build a more realistic retirement income plan.

4. Are your children financially independent?

Many parents continue supporting their children well into adulthood, and every family situation is different.
However, retirement planning becomes much simpler when your children are financially independent and you’re no longer responsible for ongoing support. Knowing those expenses are behind you allows you to focus your resources on your own long-term financial security.

5. Are your investment accounts working for you?

A well-structured retirement portfolio should do more than sit on a statement. It should help provide income.
Whether through dividends, interest, strategic withdrawals, or other investment income, your accounts should play an active role in supporting your retirement lifestyle. While markets will always fluctuate, having investments positioned to contribute to your income needs is an important part of retirement readiness.

The Bottom Line

In my experience, retirement readiness isn’t determined by a single age or account balance. It’s the result of having a reliable income strategy, manageable expenses, a healthcare plan, and confidence that your resources can support the life you want to live.
If we can help provide you with solutions to these five questions, retirement may be closer than you think.
— Tom Moore | Moore Invested
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