When Should I Retire? 6 Questions to Ask

How am I doing financially?

Finances are arguably the most important thing you’ll look at when you’re planning your ideal retirement. 401Ks, savings and social security benefits can all matter. For example, to retire early, you’ll likely need a bigger nest egg, and you’ll probably need to get by without social security for a few years.

Not looking to retire early? It’s still great to learn when you qualify for your full social security benefits and how you can make them work best for your situation. For example, if you postpone taking social security until 70, .

Talk with a financial advisor early and often to help gain an understanding of your financial situation and how it aligns with your goals.

What benefits do I have?

Benefits aren’t limited to social security. Jobs often provide many perks, such as health insurance, 401K matching, tuition assistance (for your older children), company cars and more. Take everything into account. If you’re using a company car as primary transportation, how will a new car payment impact your budget? If you have children who are in college, would tuition assistance perks make it worthwhile to work a few more years?

If you’re not comfortable with your 401k balance yet, it might also be worth working a few more years to get the benefits of company matching. Gain a full understanding of your company’s benefits from your HR team if you’re unsure and talk with your financial advisor about what’s right for you.

Do I (or my family) have health issues to consider?

Medicare kicks in at age 65. Some companies have a pre-65 retiree health insurance plan to account for a potential gap for those who retire early, but many do not these days. Talk with your company about what’s offered if you’re unsure. You can also look at Medicare benefits to understand the coverage you can expect. Then, you can consider the healthcare you and your family will require. 

For example, if your spouse will need several surgeries or has ongoing medical appointments, it may be more beneficial to work a few more years with your company’s benefits instead of Medicare. Or if you’re in good health and looking into early retirement, you may be able to find your own health insurance plan that covers your needs.

Fidelity has a resource to help you bridge retirement and Medicare.

What’s my family dynamic?

Everyone’s family is different, but there could be great opportunities to retire from your full-time career into “semi-retirement” so you can spend more time with loved ones. For example, if your family situation allows, you could offer childcare services for your grandchildren a few days a week so you still have some income — and instead of paying for daycare or babysitters, your children could keep their earnings in the family and pay you. 

Or perhaps you have an entrepreneur in the family. If that’s the case, it might be more advantageous to retire early and help support the new business. You can think about what’s going on in your family and talk about what works best for everyone. If you get creative, you might be surprised by the opportunities that aren’t always as obvious.

Do I love my job?

When it comes to planning retirement, there’s another big question: Am I happy? Some people want to work beyond 65 years old simply because they love what they do. That’s wonderful! If you’re feeling fulfilled and work is a positive way to spend your time, then keep it up. There’s no rule that you have to stop doing what lights your fire, at any age.

If you feel that you’ve outgrown your career, perhaps retiring is better for your overall well-being and mental health. You can talk to your doctor, a mental health professional and your financial advisor to discuss when the time might be right to give your final notice. 

Can I work part-time after retirement?

Consider if you need everything you’re getting from your company. You may not need your full salary, but would like to keep earning an income. If you’ve always loved movies, perhaps a part-time job at the local theater is the ticket for you. Or you could work at the gift shop at a local museum if you love being around art. Transitioning to a part-time job could be what you need to retire earlier than planned while trying something new and exciting. You can talk to your financial advisor about the best path forward for you.

It’s not too early to plan.

If you’re still not sure when it’s time to retire, don’t fret. You don’t have to make the decision in a day, and you’re able to change your mind whenever you want. Just getting the discussions started with loved ones and advisors can bring you closer to making one of the most impactful choices of your life. Take your time and stay open to the wonderful possibilities that are ahead of you. Remember, age is just a number.

The above content is shared for educational and informational purposes only. The content is not intended to be a substitute for professional or financial advice and should not be relied upon for making financial or other decisions. Please consult your attorney or financial advisor before acting on any content on this website.


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