The Ultimate Retirement Checklist for Seniors Over 50, 60, and Beyond

A woman in her late 60s sits at a wooden table, looking up thoughtfully from an open planner with a pen in hand. A travel magazine and volunteer broch — Ready to plan your next chapter? A fulfilling retirement starts here.

This retirement checklist is just what you need to get back on track!

Retirement planning isn’t just about getting ready financially but also about how you intend to spend all that extra time. So here at Helpful Resources For Seniors, we’ve created a retirement checklist that can help people set goals for hobbies, travel, volunteer work, or part-time employment, contributing to a purposeful and fulfilling retirement.

We understand that your financial objectives and life story are unique to you and your family. But this ultimate retirement checklist is an invaluable tool that ensures comprehensive preparation, offers clarity, and facilitates a seamless transition into retirement, contributing to a more secure and enjoyable post-work life.

Ready to get started? Plan for your golden years today!

Your retirement checklist between ages 50-60

A senior woman and a financial advisor seated at a table, discussing financial documents in a calm office setting. — Discussing retirement tax strategies with a trusted advisor.

Adult daughter guides her elderly mother's hand over tax documents and receipts on a wooden table, emphasizing collaborative financial planning. — Two generations working together on important tax documents.

Taxes

There are bold ways to manage and help reduce your lifetime tax burden, such as moving out of state and converting pre-tax retirement plans to a Roth IRA. Do you think you’re doing all you can to reduce your lifetime tax liability?

The best way to handle this is to consult with a wealth advisor if you aren’t sure. Keeping up with tax laws and codes can be quite difficult and there might also be techniques that make sense for you to take advantage of during this phase of your life.

A senior couple reviews financial documents, a calculator, and a laptop at a home office desk, planning for retirement. — Collaborating on important retirement planning decisions.

401(k) and IRA accounts

Consider getting the most out of your employer’s retirement plan and your IRA, including making catch-up contributions.

The IRS has annual contribution limits to abide by. So you should be aware of any laws and tax rules regarding early withdrawals. Decide if your plan allows Roth contributions and if you should contribute some or all of your retirement savings to your Roth 401(k).

A senior woman in a teal cardigan and her financial advisor reviewing investment documents on a tablet in a well-lit, comfortable room. They are engag — Carefully reviewing investment choices with an advisor to plan for the future.

Asset allocations

You should review and adjust asset allocations for any investment accounts you might have. Does it make sense to have less aggressive allocations or not?

It could depend on your cash needs, life expectancy, and your ability to manage volatility. Always get recommendations on allocations from your wealth advisor.

An older woman in a sun hat and gardening gloves harvests red tomatoes from a raised garden bed in her backyard. — Enjoying the simple pleasures of a chosen retirement lifestyle.

Senior woman in a community garden, hands in soil, planting seedlings in a raised bed. Other gardeners are blurred in the background. — Finding joy and purpose in new hobbies and community.

Lifestyle

As part of your retirement checklist, estimate how much money you’ll need every month, in addition to Social Security payments, by subtracting your taxes and expenses from your monthly income. Pay off debt that doesn’t have tax-advantaged interest, which is considered bad debt.

Mortgage debt is usually regarded as good since real estate can go up in value, and interest might be tax deductible. Think about when you might want to fully retire or shift to a a part-time job. Determine the lifestyle you want to have in your golden years and where you’ll want to live.

A senior woman and her adult daughter look at a laptop, sharing a thoughtful moment on a living room sofa. — Mother and daughter share a quiet moment discussing financial plans.

A senior couple sits on a sofa discussing something, an adult daughter watches with a gentle smile, and a child plays on the floor. — Generations come together for important family discussions.

Family

Think about how you want to juggle financial priorities that are related to your family responsibilities. For example, should you be paying debts, like student loans for your kids, or should you add money to investment and savings accounts?

Do you have elderly parents or children who need or will need your financial support? It’s good to have a plan to cover these potential needs, whether it be student loans for your kids or, Medicaid or long-term care insurance for a loved one.

Senior father and adult daughter at a kitchen table, reviewing documents together in soft window light. — Discussing important plans for the future with family.

A senior couple, a woman with glasses and a man in a plaid shirt, sit at a kitchen table reviewing documents. The woman points to text on a paper. — Reviewing policies and planning for future healthcare needs together.

Insurance

There are many insurance options to consider before and during your retirement to protect you and your family from any potentially catastrophic expenses. To cover healthcare costs, you should consider contributing to an HSA. If you already have one, it might be time to increase your contributions.

Do you have family members who who’ll need insurance after you retire? It’s essential to remember that people aren’t eligible until 65 years old for Medicare. And Medicare doesn’t apply to domestic partners, spouses, or dependents. Life insurance is another good option for taking care of your family.

Whether or not you have life insurance through an employer, you can get a separate policy to potentially use as a wealth transfer tool. Are you interested in annuities as extra income in your golden years? Then, look into the advantages and disadvantages of annuities and whether they’re the right way to go.

You should also get quotes for long-term care insurance to cover care using assisted living, home healthcare, or nursing home care. Remember that the long-term care environment has changed a lot, and there are alternatives for life insurance with long-term care riders.

Ask your wealth advisor what’s available in your state and whether it’s a good option for you. It’s better to apply early for these coverages because you might become uninsurable once you’re diagnosed with a medical issue.

Senior woman's hands carefully place a document into a labeled file in a wooden box on a desk with other organized papers. — Putting important papers in order for peace of mind.

Estate planning

It’s never too early to have an estate plan in place. If you happen to own real estate, have retirement accounts, including a 401(k) or IRA, have children, or have insurance policies, then you most likely require an estate plan.

If you don’t have children that live nearby or don’t want to burden them, it might be worth considering a corporate trustee for assets that are held in a trust.

Your retirement checklist between ages 60-70

Taxes

There are usually essential tax strategies to consider for your retirement plan between ages 60-70 because those who are leaving the workforce typically fall into a lower tax bracket after they’ve retired.

If you have elderly parents with limited income and are paying their medical or long-term care expenses, you might be able to claim them as dependents and their costs as a tax deduction. Consider talking to a certified public account about tax strategies.

An older woman, wearing reading glasses, thoughtfully reviews a financial statement at a kitchen table with a pen and a mug of tea. — Reviewing a financial statement over a warm cup of tea.

IRA and 401(k) accounts

If you’re still earning income, contribute to an IRA or qualified plan through your employer. And have a withdrawal strategy ready for when you retire.

It might also be worth delaying distributions if you have a pension or accelerating distributions to take advantage of lower income tax brackets.

Asset allocations

Are your investments fully diversified globally in both fixed-income and equities? It might be time again to adjust asset allocations if you prefer an income strategy from investments over a growth strategy during this life phase.

Lifestyle

A good retirement plan includes making financial decisions and planning how you want to spend your time. If you connect your identity to your work or don’t have any hobbies, now’s the time to find some new interests.

Begin planning for a date when it’s reasonable and you feel comfortable to retire. You should also think about exploring volunteer opportunities when you’re retired and have more time on your hands.

Family

If you have a spouse who isn’t retiring at the same time as you, you may want to discuss how your relationship could change at this junction. If you’re providing care for elderly parents or any other dependents, think about how you want to allocate your resources and time in your golden years.

How much time, if any, do you want to spend caring for your grandkids? Take a look at your financial retirement plan to decide how much you want to financially support adult kids or grandchildren.

Insurance

Are you ready for extra healthcare costs after retirement and possible long-term care? Consider how you can fill in the healthcare insurance gap if you retire before being eligible for Medicare at 65.

According to Forbes, the average cost nowadays for a single plan for a 60-year-old on the U.S. government’s Health Insurance Marketplace is around $995 a month and $1,987 per month for couples. Also, revisit your other insurance policies to make sure they’re up to date and still align with your wealth management goals.

Social Security

Determining when to claim your Social Security benefits will depend on your retirement age, benefit amount, marital status, additional income, and health. The monthly Social Security payment was $1,910.79 for an average retiree in 2024.

Even if your payment surpasses the average, you may want to consider taking Social Security benefits later on to receive higher payments.

Remember that claiming benefits before reaching your full retirement age will result in a lower monthly check and potential repayment if you earn over the income threshold. If you were born in 1960 or later, the retirement age for full Social Security benefits is 67.

Estate planning

Wills and any other estate plans are more significant during this time, as does speaking with family members about long-term financial needs. If you don’t already have an estate plan, it might be time to consider one.

If you already have one, be sure to update it to reflect any changes in life events and tax laws. This Estate Planning Guide Book from Amazon can be a huge help!

Be sure to leave a comments and let us know what you think of this retirement checklist. And if you found this article helpful, you might also like: 8 Key Social Security Changes Coming This Year

For expert guidance on senior health and finance, visit National Institute on Aging (NIA), Centers for Disease Control and Prevention (CDC), Medicare.gov and National Institute of Mental Health (NIMH).