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How do you know when it’s the right time to retire?

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Dear Grace,

How do you know when it’s time to retire?  I’m 69 years old and so very unhappy at my job right now. I’d love to quit, but I don’t know what to do next. Retirement feels like a big leap. Am I crazy for wanting to leave the workforce on a high note? 

– (Still) At Work in Alabama


Dear (Still) At Work,

The decision to leave a job—no matter how much we may hate it—is not an easy one to make. Retirement is a big step and taking the plunge can be scary, even if it’s something you’ve looked forward to for a while now. 

Fortunately (or unfortunately), there is not a single “right” way to do things or “perfect” time to make a change in your life. Every choice we make presents its own opportunities and challenges, so it’s really a question of finding the combination and balance that works for you. Here’s some things you can do to make sure you’re making the right choice for you: 

Make a plan. Change is hard and it can be scary to take such a big leap after decades in the workforce. But what I’m hearing from you is that some of that fear comes from not knowing what life will look like if you do. Instead of asking yourself simply “should I retire now?” ask yourself “How would I like to retire?” Take some time to think about or journal what your response is to that question. Consider your finances, career aspirations, interests, and health. Knowing what you want your retirement to look like will give you a goal that you can plan for—and be excited by, too. 

Test the waters. Perhaps instead of looking at the decision as being fully in or out, you could take things slowly and start by cutting down on your hours or applying for part time work somewhere that might bring you more joy. This way you could get a preview of what retirement may feel like, while keeping some financial security, too. Many people find suddenly having all that time off to be very jarring, and end up seeking out part-time work or volunteer opportunities. This would help you to discover if that would be the right choice for you. 

Talk to friends who’ve done it. We often forget that one of our greatest resources are friends who have been in similar situations. Reach out to your retired friends and ask them what they would have done differently—or what advice helped them make the decision that felt right for them. Their experience may offer you some clarity as to what you really want, and the best ways to ease into this next chapter on your terms. 

I know starting a new chapter can be full of doubt and anxiety, but there’s also excitement and adventure, too. You’ve worked hard your whole life, (Still) At Work, and are deserving of all of the fun and happiness that comes next!

With love and joy,

Grace