Wealth management

The big retirement question

Melody Evans hears some version of the same question nearly every time a new client walks through her door. Am I on track? Do I have enough? When can I actually retire? 

Evans, a vice president TIAA Wealth Management advisor in TIAA’s Portsmouth, NH, office, says those questions all fall under the same umbrella—retirement readiness. And five years out from retirement is an ideal time to start answering them.

“That’s when you need to move away from back-of-the-napkin calculations,” she says. “We need to make sure you’re actually saving enough, based on the rate of saving you’re doing, how much you think health insurance is going to cost, or even based on the hobbies you want to take up in retirement.”

The good news, Evans says, is that five years out still leaves time to course-correct. Some clients discover they need to work a bit longer or consider a phased retirement with part-time work. Others get a pleasant surprise. “Sometimes I have people using a number like their Social Security full retirement age, and we run the numbers and basically tell them they could retire two years earlier,” she says.

With that in mind, here are five conversations worth having with your advisor now. And if you don’t yet have an advisor, perhaps it’s time to make your first appointment.

1. Are you actually on track?

Before you can plan for retirement, you need to know where you stand. That means trading rough estimates for real projections—factoring in your savings rate, anticipated expenses, health care costs, and the lifestyle you’re envisioning. If there’s a gap, catch-up contributions are one of the most powerful tools available. For 2026, savers age 50 and older can contribute an extra $8,000 on top of the $24,500 base limit for 401(k) and 403(b) plans. Those between 60 and 63 get an even bigger boost under the SECURE 2.0 Act—$11,250 above the base limit.¹ Evans also points out that some clients have access to accounts they’ve never tapped, like a 457(b) plan, that could provide additional runway.

2. Think about where—not just how much—you’re saving

Most people spend their entire career saving in one place: their employer-sponsored retirement plan. That works, but five years out is a good time to ask whether it’s still the optimal strategy. Evans draws a distinction between asset allocation—the mix of investments within your accounts—and asset location, meaning which types of accounts you’re using. “For the same dollar that you’re saving, question is whether there’s a better place for us to save it than the strategy you’re using right now,” she says. 

Depending on your situation, that might mean redirecting some savings into a Roth 401(k) or 403(b) for tax-free income later or maxing out a Health Savings Account (HSA) to build a reserve for future health care costs. It could also mean building up accessible cash in a plain old bank or brokerage account to fund near-term goals—a big trip, a new boat, or a down payment on a summer house—that you won’t want to fund with a large, taxable withdrawal from a pretax retirement account. According to Evans, clients sometimes arrive at retirement with plenty saved, only to realize that every dollar they touch gets taxed as ordinary income. “They have no other bucket to pull from,” she says.

With five years still on the clock, there’s time to fix that.

3. Build your retirement income plan

Saving for retirement and generating income from it are two very different things. The transition requires a deliberate strategy. One of the most important—and most misunderstood—pieces is Social Security timing. Many people assume that when they retire and when they claim Social Security have to be the same decision. They don’t.

“You could retire at 65 and claim Social Security at 68,” Evans says. “We just have to figure out how to generate income from your investments before then.” Waiting to claim can possibly result in a meaningfully higher monthly benefit—potentially 77% more at age 70 compared to claiming at 62.²

Your advisor can also help you think through the sequencing of withdrawals across taxable, tax-deferred, and Roth accounts. If an annuity is part of your financial picture, it’s worth understanding sooner rather than later how it fits into your income stream in retirement. A guaranteed income foundation, Evans notes, may offer greater flexibility with the rest of your portfolio—allowing you to hold higher-risk, higher-return investments than you otherwise might, because your overall portfolio has a portion designed to cover your basic income needs.

4. Rightsize your investment risk 

As retirement approaches, matching your portfolio’s risk level to your actual time horizon matters more than ever—but it’s not as simple as just dialing back equities across the board. The right allocation depends heavily on when you’ll actually need to tap each account. A client retiring at 65 who won’t touch their retirement savings until 75 (thanks to other income sources) probably shouldn’t be invested as if withdrawal day is tomorrow. The key variables, Evans says, are your tolerance for risk, how dependent you are on the portfolio for income, and the time horizon for each pool of money. Five years out is the right moment to think through all three with an advisor. 

5. Get your accounts organized and your documents in order

Perhaps the most underappreciated item on any pre-retirement checklist is simply getting your financial accounts in order before you need to start using them. For many TIAA clients—particularly those who have moved between institutions over the course of a career—that means tracking down old retirement accounts that have been sitting dormant for years and consolidating them, perhaps into an IRA.

Along the way, every account’s beneficiary designations should be reviewed. These designations override your will. An outdated one—one that named an ex-spouse as primary beneficiary or doesn’t include children who came along after the account was opened—can direct assets in ways you never intended.

“You’ve done a great job saving the money,” Evans tells clients. “Now we need to get these accounts ready for use. For years, your focus has been growing these accounts, not using them. So, let’s think about how do we make them easy to use when the time comes.”

The bottom line

The five years before retirement aren’t a time to coast, but they don’t have to be nerve-wracking. Says Evans, “When we start all this planning five years out from retirement, they’re nice, easy, educational conversations. Nobody’s stressed out.”

It’s why you should schedule your pre-retirement checkup with an advisor now. (Your future self may thank you!) Don’t yet have an advisor? Schedule an appointment.