When does buying an annuity make sense for retirement income?

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You've spent decades building your retirement savings. Now, as retirement approaches, you're faced with a critical question: How do you turn that nest egg into reliable income that will last as long as you do?

If you've been researching retirement income strategies, you've likely encountered annuities. Some advisors swear by them. Others warn against them. The truth? Like most financial decisions, the answer isn't one-size-fits-all.

The Promise and the Problem

An annuity is essentially a contract with an insurance company. You hand over a lump sum, and in return, they promise to pay you a stream of income, often for the rest of your life. For many retirees, that guarantee sounds like exactly what they need.

But annuities come with trade-offs. They can be expensive, complex, and inflexible. Understanding when they make sense, and when they don't, could save you tens of thousands of dollars and years of regret.


When Annuities Make Sense

You Need Guaranteed Income to Cover Essential Expenses

If Social Security and any pension income don't fully cover your essential expenses (housing, food, healthcare, utilities), an annuity can fill that gap. The psychological benefit of knowing your bills are covered, no matter what the market does, can be worth the cost.

Consider a couple who needs $6,000 per month to cover essentials but only receives $4,000 from Social Security. A single premium immediate annuity (SPIA) that generates an additional $2,000 per month creates a reliable income floor.

You're Worried About Outliving Your Money

Longevity risk (the risk of living longer than your savings last) is one of the biggest fears retirees face. If you're in good health with a family history of longevity, and you're concerned about portfolio sustainability over 30+ years, an annuity with lifetime income can provide peace of mind.

You Have a Pension Lump Sum Decision to Make

If your employer offers you a choice between a monthly pension or a lump sum payout, you're essentially being asked whether to keep your existing annuity or convert it to a do-it-yourself portfolio. Sometimes the pension offer is actuarially generous. Other times, buying your own annuity in the open market might provide better value.

You Want to Simplify in Later Retirement

As you move into your 70s and 80s, managing investments can become more burdensome. An annuity can simplify your financial life by providing predictable income without requiring ongoing portfolio management decisions.


When Annuities Don't Make Sense

You Have Ample Assets Relative to Your Spending

If your portfolio is large enough that you're only withdrawing 2-3% per year, you probably don't need the insurance of an annuity. You're already positioned for sustainability, and you'd benefit more from maintaining liquidity and flexibility.

You Need Access to Your Principal

Most annuities are illiquid. Once you've purchased one, accessing your principal can be difficult or impossible. If you anticipate large expenses (major home repairs, long-term care, helping family members), you may need that flexibility more than guaranteed income.

You're in Poor Health

Annuities are priced based on average life expectancy. If you have serious health issues that may shorten your lifespan, an annuity is likely a poor value. You'll be paying insurance company pricing for longevity protection you may not need.

The Costs Are Too High

Variable annuities and indexed annuities often come with high fees, surrender charges, and complex features you may not need. If the total annual costs exceed 2 to 3%, you're likely better off with a diversified portfolio or a simpler, lower-cost immediate annuity.

You Want to Leave a Legacy

When you purchase a life-only annuity, any remaining principal typically goes to the insurance company when you pass away, not to your heirs. If leaving money to family or charity is a priority, annuitizing all your assets works against that goal.


A Balanced Approach

For many retirees, the answer isn't all-or-nothing. A thoughtful strategy might involve:

  • Covering essential expenses with Social Security, pensions, and potentially a portion of savings in an immediate annuity
  • Keeping the remainder invested in a diversified portfolio for growth, flexibility, and legacy goals
  • Considering a deferred income annuity that starts payments at age 80 or 85 as "longevity insurance"

This approach provides both security and flexibility: the income floor you need with the growth potential and access you want.


Questions to Ask Before Buying

Before you purchase any annuity:

  • What percentage of my retirement income needs does this annuity cover?
  • What are the total annual costs, including all fees and charges?
  • What happens if I need to access my principal?
  • Am I comparing this to other income strategies, not just doing nothing?
  • Is this annuity from a highly rated insurance company?
  • Do I understand all the features, riders, and restrictions?

The Bottom Line

Annuities aren't inherently good or bad. They're tools. For the right person in the right situation, they can provide valuable income security. For others, they're an expensive solution to a problem they don't have.

The key is understanding your specific situation: your income needs, your other resources, your health, your legacy goals, and your comfort with market volatility. An annuity should fit into a comprehensive retirement income strategy, not be your entire strategy.


This information is for educational purposes only and should not be considered tax, legal, or investment advice. Annuity guarantees are backed by the financial strength and claims-paying ability of the issuing insurance company. Consult with a qualified financial advisor and carefully review all annuity contract terms before making any purchase decisions.

Asset allocation and diversification do not ensure a profit or protect against loss.

Advisors associated with Chesapeake Financial Planners may be either (1) LPL Financial Registered Representatives offering securities through LPL Financial, Member FINRA and SIPC, and investment advisor representatives offering investment advice through Great Valley Advisor Group; or (2) solely investment advisor representatives offering investment advice through Great Valley Advisor Group and not affiliated with LPL Financial. Great Valley Advisor Group, and Chesapeake Financial Planners are separate entities from LPL Financial.

Chesapeake Financial Planners | 2402 Scotlon Ct, Forest Hill, MD 21050 | (410) 652-7868 | www.chesapeakefp.com

© 2026 Chesapeake Financial Planners | Not to be reproduced in whole or in part. All rights reserved.

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.

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