CheckmateFinancial Group

M–F · 9am–8pm ET · Hablamos español · Falamos português

Learning center
Annuities6 min readUpdated June 2026

When does it make sense to buy an annuity?

Usually when guaranteed income matters more than upside. Within ten years of retirement, or wanting a paycheck you cannot outlive.

The short version
  • An annuity makes the most sense when you want income you cannot outlive, backed by the issuing carrier.
  • Common fits: within 5-10 years of retirement, conservative savers, and surviving spouses who need a stable check.
  • It often works best alongside Social Security and savings, covering your fixed costs so the rest can stay invested.
  • It is not for everyone. If you need full access to the money soon, an annuity may not fit. A licensed agent will tell you.
On this page

An annuity makes sense when you want a paycheck you cannot outlive and you value that more than chasing the highest possible return. The classic fits are clear: within 5-10 years of retirement, conservative savers who dislike market swings, and surviving spouses who need a steady check. If running out of money in retirement is your worry, this is the product built to answer it.

It is a contract with an insurance carrier that turns savings into guaranteed income, and the guarantee rests on the carrier’s financial strength. It is not the right move for every dollar or every person. The clearest way to know is to look at the moments where it tends to fit, and the one where it usually does not.

Are you within 5-10 years of retirement?

This is the classic window. Close enough to retirement that a market drop right before you stop working could hurt, but still early enough to set up income. An annuity lets you lock in a portion of your savings against market loss and line up a future stream of payments. You stop guessing about timing. You start building a floor.

A guaranteed lifetime income rider is often what people add here. A rider is an optional feature attached to the contract. This one turns your balance into payments that continue for life, however long you live, guaranteed by the carrier. You can outlive a savings account. You cannot outlive lifetime income built this way.

Do you want income you cannot outlive?

Social Security and a pension, if you have one, pay you for life. Most other savings do not. They pay until the balance hits zero, and then they stop. An annuity is the tool that closes that gap. It converts a lump sum into a check that keeps coming, on a schedule you choose, for as long as you are here.

A savings account asks how long your money will last. Lifetime income asks how long you will live, and answers either way.

Are you a conservative saver, or a surviving spouse?

Some people simply do not want their retirement money exposed to the market. If a down year would make you anxious, or make you sell at the wrong time, a product that protects your principal from market loss can be worth more than a few points of potential return. Conservative is not a flaw. It is a strategy, and an annuity is one of the few places it earns growth without market risk to principal.

Planning for a surviving spouse is another strong fit. When one partner passes, household income can drop hard. One Social Security check may stop. A pension may shrink or end. A surviving spouse is often left managing a lump sum alone, at a tough time, with no steady replacement coming in. An annuity can turn part of that money into a reliable check, so the income does not lean on perfect investment decisions during grief. Many contracts can be set up to keep paying a spouse for life.

When might an annuity not fit?

Here is the honest part. An annuity is not always the answer, and any agent worth trusting will say so. The table below sorts the common reasons it fits against the reasons it often does not.

When an annuity tends to fit, and when it usually does not. Educational comparison, not advice for your situation.
Your situationAnnuity often fitsAnnuity often does not fit
Timeline for the moneyYou will not need this balance for yearsYou may need the full balance soon
Emergency savingsYou already have a liquid cushion in placeYou have no emergency fund yet
Comfort with marketsA down year would worry youYou want maximum growth and can ride out swings
Existing guaranteed incomeSocial Security alone does not cover your billsYour fixed costs are already fully covered

An annuity should solve a real problem you have, not fill a slot on a sales sheet. Make sure it fits your situation before you commit to one.

How does it sit alongside everything else?

An annuity rarely stands alone. The common approach is to cover your essential, must-pay costs, housing, food, healthcare, with guaranteed sources: Social Security, any pension, and an annuity. Then your remaining savings can stay invested for growth and flexibility, because the bills are already handled. The annuity is the floor. The rest of your portfolio is the upside.

Whether the timing and the fit are right for you is a personal call, and it depends on numbers only you have. A licensed Checkmate agent can map your income sources, find the gap, and show you whether an annuity belongs in the plan. If it does not, you will hear that plainly.

This article is for general education only. It isn’t tax, legal, or individualized financial advice. Coverage is subject to underwriting approval, and product and carrier availability varies by state. For guidance on your situation, talk to a licensed Checkmate agent.

Have a question?

Talk it through with a licensed agent.