Early Retirement Checklist

If you’ve ever yearned for an early retirement, you’re not alone.

A small but growing contingent of working Americans have made it their mission to eliminate paycheck dependency well ahead of the traditional age of retirement.

More than one-third of Gen Zers, millennials, and GenXers said they plan to retire before age 65, according to the most recent research from GOBankingRates. Men were most likely (32 percent) to express confidence in an early exit, versus 25 percent of women.1

The mostly millennial-led FIRE community, which stands for “financial independence, retire early,” is also gaining traction on social media with 26,000 followers on Facebook alone. Many proudly declare that they plan to exit the workforce in their early 40s.

But planning to retire early and following through are two different things.

To start with, you must carefully consider:

  • Your reason for wanting to retire early
  • Health insurance coverage
  • Physical and emotional wellness

Explore your reason

FIRE aficionados should be sure they have a clear vision of what it is they hope to achieve by retiring early. Is it to volunteer more, travel the world, play a more active role in a nonprofit you support? The better defined your plan, the more likely you are to meet your expectations.

If it’s a better work-life balance you seek, try changing employers or using your work experience to shift gears into a more forgiving industry.

Indeed, an early retirement means different things to different people. Some view it as a total departure from the workforce, which requires significant savings depending on the age at which they retire. Others define it as having enough personal savings set aside to quit their day job and start a home-based business, do part-time consulting, or pursue a more meaningful (but lower paying) job.

A retirement plan that builds in flexibility and allows you to supplement your savings as needed can help you sleep easier at night.

How much I need to retire early?


It goes without saying that you can’t quit work until you’ve got enough saved, but just how much do you need? That depends on your expenses, your age, and your health insurance coverage.

It may help to segregate your savings goal into two distinct phases:

  • The money you will need available to cover the bills before you reach the age of Medicare and Social Security eligibility.
  • The money you need saved in your tax-deferred retirement accounts (401(k)s and IRAs) to provide for your needs after you reach age 59-1/2.

Remember, you can’t start claiming Social Security until age 62 at the earliest, and many retirees delay benefits until at least their full retirement age at 67 to permanently augment the size of their monthly benefit.

Similarly, you generally can’t withdraw money from your tax-deferred retirement accounts such as your traditional Individual Retirement Account or 401(k) until age 59-1/2 without incurring taxes, plus a hefty 10 percent penalty.4,5

That means you’ll need enough saved to get you over the hump until your retirement accounts and Social Security become accessible.

Be sure to factor in projected expenses, such as college tuition costs for your kids or a wedding for your child, if you plan to chip in.

A 2020 survey by the AARP and National Alliance for Caregiving found 53 million Americans had provided unpaid care to an adult with health or functional needs.6 The average family caregiver spends roughly $7,2000 per year, or nearly 20 percent of their annual income, on out-of-pocket costs, according to AARP estimates.

Expect the unexpected

An oversized emergency fund of at least a year’s worth of living expenses is a must for early retirees, creating a buffer for years when the stock market may be limping along or a medical expense crops up.

Saving enough money and projecting your living expenses accurately is no easy task. Perhaps that explains why less than half (47 percent) of the higher income respondents to MassMutual’s survey said they were confident in their ability to retire at their intended age.

It helps to work with a trusted professional who understands your financial goals and can help you solve for variables, including whether your house will be paid off, tax efficiency, the effects of inflation (which erode purchasing power), and whether the numbers only work if you move to a more tax-friendly state with a lower cost of living.

Think, too, about your safety net in case your early retirement plan doesn’t work.

Consider, for example, whether you should budget for homeowners or renters insurance, whether you will carry life insurance, and how you will ride out Wall Street’s inevitable bear markets. Will you be able to go back to work, if needed, to generate some supplemental income?

Healthcare coverage

The fly in the ointment for many FIRE fans is healthcare coverage. You aren’t eligible for Medicare federal health insurance until age 65, so unless your spouse plans to continue working and can cover you on his or her health plan, you’ll need to factor the costs of private insurance into your budget.

Depending on the size of your family, private coverage can set you back several thousand dollars a month.

During the accumulation phase, while you are still working, it may help to select a high deductible health plan with a health savings account (HSA) component, if available through your employer.

According to the Fidelity Retiree Health Care Cost Estimate, a 65-year-old individual who is covered by Medicare and retires this year will need roughly $165,000 in today’s dollars for out-of-pocket medical expenses throughout retirement, not including any costs associated with long-term care.

Your physical and emotional well-being

Lastly, spend some time planning for your emotional and physical well-being. Will you miss the social interaction of a work environment? Does your spouse support your goal of an early retirement? Will the workweek feel lonely if most of your friends and family are still doing the 9 to 5 grind?

Making the switch from collecting a paycheck to living off your savings is a challenging task at any age. For those who intend to retire early, however, it’s all the more crucial to plan ahead — and consider all options — so they can make the transition to financial independence with confidence.

Provided by Matthew Clayson, courtesy of Massachusetts Mutual Life Insurance Company (MassMutual). CA Insurance License # 0I01304
©2024 Massachusetts Mutual Life Insurance Company, Springfield, MA 01111-0001 
MM202708-310101