We all reach a point where continuing to work may cost us more than stepping into retirement. But how do you know when it’s the right time?

Many people delay retirement for financial reasons—income, benefits, 401(k), and so on. However, at some stage, the marginal benefit of earning more money starts to diminish, and continuing to work can take a toll on your time, health, and happiness.

If you’re wondering whether it’s time to retire, here are five signs that might indicate you’re ready to make the transition.

1. You Realize That Time Is the Only Non-Renewable Currency

Money comes and goes. Even if you face financial setbacks, there’s usually a way to earn or recover what you’ve lost. But time? That’s something you can never get back.

Early in our careers, we prioritize making money, often at the expense of our time. But once you’ve built a financial cushion, time becomes far more valuable than money.

James Conole, founder of Root Financial, shares that he’s worked with many people who delayed retirement, believing they had all the time in the world. Sadly, some fell ill or even passed away just months after retiring.

In their final days, they weren’t thinking about their bank balance or their last paycheck—they were thinking about time. The time they wished they had to travel, spend with loved ones, or simply enjoy life.

If you’re financially prepared but keep postponing retirement, ask yourself: Am I trading irreplaceable time for something I no longer truly need? Finding the right balance between financial security and quality of life is key.

2. Your Health Is Taking a Hit

For many people, the final working years are also their most stressful. Decades of grinding, long hours, and meeting financial responsibilities can leave you feeling exhausted. The result? Burnout, stress, and even serious health conditions like anxiety, depression, high blood pressure, or heart disease.

If work is negatively affecting your health, it might be time to step back. Retirement isn’t just about quitting a job—it’s about reclaiming your well-being. Without the constant stress of work, you have the opportunity to exercise, eat better, reduce stress, and focus on self-care.

The last thing you want is to finally retire, only to be too unwell to enjoy the freedom you’ve worked so hard for.

3. You Want to Spend More Time with Family and Friends

The quality of our relationships plays a huge role in our happiness. Yet, for most working professionals, time with loved ones is often limited. Between work, commuting, errands, and everyday responsibilities, there’s little time left for meaningful connections.

Many people intend to stay in touch with friends, spend more time with their kids or parents, or nurture their relationships—but work keeps getting in the way. If you’re financially ready for retirement, consider whether your job is costing you valuable moments with those who matter most.

Work can be fulfilling, but it shouldn’t come at the expense of your relationships. If you find yourself missing out on precious time with family and friends, it may be a sign that retirement is the right move.

4. Your Best Years Are Limited

Some people look at retirement and think, I still have 30 years left—I can afford to work a little longer. But the reality is, not all years are created equal.

Your ability to travel, engage in hobbies, and enjoy an active lifestyle is much higher between 60 and 70 than between 80 and 90. Many retirees regret waiting too long, only to realize that their best years—the ones where they had the health and energy to truly enjoy life—have passed.

James Conole explains that many people put off retirement thinking they’ll have plenty of time later. But age 62–65 might be the best years to enjoy new experiences. While you may still be healthy at 75 or 80, your energy and physical ability will likely decline.

If you’re holding off on retirement just to save a little more money, consider this: The extra money might not be worth sacrificing the healthiest and most vibrant years of your life.

5. You’re Financially Ready

For many, the hardest part of retirement isn’t the finances—it’s the psychological shift. After spending 30 or 40 years working, it’s difficult to suddenly stop. Work becomes part of our identity, and even when we don’t love it, we often keep going simply because it’s what we’ve always done.

But continuing to work just for the sake of working can come at a high cost. If your savings, pension, Social Security, or other income sources are enough to sustain the lifestyle you want, ask yourself: Am I working out of habit, or do I genuinely love what I do?

If your work brings you fulfillment and joy, by all means, keep going. But if it’s holding you back from living the life you truly want, it might be time to step away.

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Final Thoughts

Retirement is a deeply personal decision, and there’s no universal right time. However, if you recognize any of these signs in your life, it may be worth considering whether it’s time to make the transition.

The most important thing is to retire on purpose—not just financially prepared, but emotionally and mentally ready to embrace this next chapter.

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Credits:

This blog post is based on insights shared by James Conole, founder of Root Financial, in his YouTube video. The content has been adapted for readability and clarity. You can watch the original video and explore more financial guidance from Root Financial here.