Retirement, ironically, can take work. It requires us to restructure how we think about both our time and our finances. Tax planning, in particular, tends to take more of a center stage role. If you’re approaching retirement—or are already there—there are several tax strategies worth considering.
But before reviewing individual strategies, it’s worth looking at a more fundamental point, which is that when you transition to retirement, the overall objective of tax planning changes as well. During our working years, the goal usually is to minimize our tax bill each year. But in retirement, the objective is different: It’s to minimize our total lifetime tax bill.
To understand this idea, consider a simple example: Suppose you have two accounts: a tax-deferred IRA and a Roth IRA. Withdrawals from the traditional IRA will be taxable, while Roth withdrawals will be tax-free. If you simply wanted to minimize your tax bill in a given year, you could draw all of your living expenses from your Roth IRA. But if you did that every year, eventually your Roth IRA would be exhausted, and then you’d have to turn to your tax-deferred account for all future withdrawals.
The result: Because withdrawals in later years will lean so heavily on tax-deferred accounts, that could force your income into higher brackets, causing your aggregate tax bill to be higher than if you’d more evenly weighted withdrawals over the years. Because of this dynamic, job number one for every retiree is to be intentional in choosing a tax bracket that will, more or less, remain the same throughout retirement. How should you go about choosing a bracket? I see it as a three-step process.
First, you’ll want to estimate your potential maximum tax rate in retirement. That will most likely be in your mid- or late-70s, after you’ve started both Social Security and required minimum distributions (RMDs). Then you’ll want to estimate the minimum. That’s typically in the years immediately after retirement, before those other income sources come online. Finally, to choose an ideal target for the duration of retirement, you’ll want to choose a rate somewhere between the estimated minimum and maximum.
Now let’s turn to specific strategies:
Roth contributions. The first is one you can implement even before you enter retirement. Suppose you normally contribute to a standard tax-deferred 401(k) or 403(b). That usually makes sense during your working years, when your tax rate is at a high point. But for some people, this playbook has a wrinkle. If your plan is to move gradually into retirement, perhaps working a reduced schedule for some time, then your tax rate might also drop. And if it drops enough, it might make sense to shift your retirement contributions to your employer’s Roth 401(k) or Roth 403(b). You’ll forgo the tax deduction, but if your tax rate is lower, then the benefit you’ll be giving up will be smaller. And it’ll allow you to build up valuable Roth money.
Medicare surcharges. Once you’ve entered retirement, if you’re on Medicare, you may be frustrated by the income-related surcharges added to your premiums. Because these surcharges are calculated on a two-year lagged basis, they can be quite high in your first years of retirement. Fortunately, the government has a process for appeal. Look for Form SSA-44. You’ll notice that it offers eight possible reasons to request an adjustment, one of which is “work stoppage”—in other words, retirement.
Roth conversions. In your first full year of retirement, you might consider a Roth conversion. In the past, I’ve described the mechanics and the many benefits of conversions. But in short, the key is that Roth conversions smooth out your income to help you remain in your chosen tax bracket each year.
Portfolio structure. The objective of Roth conversions is to reduce future RMDs. That, in turn, can help keep a lid on your future tax rate. Portfolio structure can also help to limit future RMDs. To do this, you’ll want to house your fastest-growing assets—typically stocks—in your Roth IRA, to take advantage of the tax-free growth. And you’ll want to locate your slowest-growing assets—typically bonds—in your tax-deferred accounts. The result: Your tax-deferred account will grow much more slowly, thus limiting the growth of future RMDs.
Roth IRAs are most attractive for holding stocks, but you can also house stocks in your taxable account. Yes, this means you’ll incur capital gains taxes when you sell them down the road. But capital gains rates are often lower than the ordinary income rates that apply to withdrawals from tax-deferred accounts. And at death, a cost basis step-up applies to appreciated assets.
Charitable giving. Suppose you’re further along in retirement and contending with RMDs that exceed your annual expenses, causing your tax rate to creep up. After age 70½, you could turn to a strategy known as qualified charitable distributions (QCDs). To see how this strategy works, consider a retiree whose RMD is $200,000 but who only needs $180,000 for expenses. This is where QCDs can be a godsend. If this retiree were to give $20,000—or any amount up to $20,000—to a charity, it would count toward his RMD but would not add to his taxable income.
Monitoring the mix. If you’re still many years from retirement, are there any steps you can take to plan ahead? Two strategies are worth considering. First, keep an eye on the mix of your retirement accounts. Sometimes, high-income taxpayers become too enthusiastic over tax-deferral strategies, employing, for example, cash balance plans that end up deferring six-figure sums each year. While these can make sense, they can also have an unintended consequence: If tax-deferred balances grow too large, the resulting RMDs can push a retiree back into a very high tax bracket later in life. This is unusual, but I have seen it. So it’s worth taking a minute periodically to do some projections, to see where your retirement balances might end up down the road. You could then adjust your contributions, if need be.
Direct indexing. Another suggestion for those in their working years: In the past, I’ve discussed the concept of direct indexing. Instead of owning an S&P 500 index fund, for example, a direct indexing service would purchase all 500 stocks individually. While this might sound unwieldy—and the cost is certainly higher—it can deliver a benefit over time. When you reach retirement and want to take withdrawals, you’ll have much more control over the gains you realize each year. You’d also have the option of donating the most highly-appreciated stocks to charity.
Because direct indexing has pros and cons, you shouldn’t view this as an all-or-nothing decision. You might establish a separate account with just a portion of your assets dedicated to this strategy.