When it comes to politics and religion at the Thanksgiving dinner table, ‘tis often the season to change the subject. But there’s one taboo topic that many people may want to broach when the family gets together this holiday season: money. Or more specifically, what happens to it when the older generation passes on.

Despite the fact that an estimated $124 trillion is expected to change hands through 2048, 56% of adults in the US have no estate planning documents, such as trusts, wills and medical and financial powers of attorney, according to Trust & Will’s 2026 estate planning report earlier this year. So while families may not actually want to get into the nitty gritty of legacy planning and wealth transfer over the turkey and mashed potatoes, it is important for them to spend some time on the books to chat through what comes next. And financial advisors can offer tips to start the conversations.

“Estate planning is one of the most important topics but one of the least talked about,” said Michael Walstedt, founder of Reliant Wealth Advisory.

It’s Not Personal

Even though a successful estate planning conversation may result in paperwork, that’s not where to start:

• “Instead of asking, ‘Do you have a will?’ try sharing your own experience first,” said Corinna Rose, paraplanner at Bell Investment Advisors. That could look like explaining how straightforward making a will was for the person initiating the conversation. “People tend to be much more receptive when they feel invited into a conversation rather than interrogated.”
• Because money conversations can get emotional quickly, it’s best to keep conversations practical, not personal, Walstedt said. He advises clients to start with discussing where various assets are located as opposed to who is getting what.
• Rose said she advises families to remember that estate planning isn’t about preparing for death. “It’s about making life easier for the people you love.”

A New Tradition. Estate planning laws and family circumstances can change over time, so just because a plan is in place doesn’t mean a family can forget it until they need it. “If it has been more than five years since you last reviewed your documents, or you’ve moved to another state, it may be time to revisit your estate plan to make sure it still reflects your wishes,” said Michael DeMassa, founder of Forza Wealth Management.

Now that’s a lot of cheddar.

US household investable wealth is now more than $100 trillion, according to new research from H&W (formerly Hearts & Wallets), an amount of money that has tripled since 2012. It’s an astonishing level of growth, but there are more interesting findings under the surface, H&W founder Laura Varas said. Defined contribution accounts like 401(k)s are closing the gap with individual retirement accounts, for example, while in-plan retirement income strategies and annuities are gaining greater attention. It’s all a reminder for advisors that clients have a lot of choice about where to park their assets as they save for the long-term future.

“IRA rollovers are still happening at an amazing rate,” Varas said. “Our estimate is that rollover flows into IRAs topped $1 trillion last year across as many as 8 million transactions, which are both impressive milestones. DC plans held their own, though.”

Catching Up

Taxable accounts still hold the lion’s share of investable assets, at $66 trillion, remaining both bigger and faster-growing than consumer-controlled retirement accounts, which stand at $36.5 trillion (excluding pensions). But that’s not the whole story:

• The 10- and 5-year compound annual growth rate for taxable accounts are 9.2% and 8.7%, respectively, both higher than or equal to the same period CAGRs for consumer-controlled retirement accounts (8.1% and 8.7%).
• For the 3-year period, however, retirement accounts outpaced taxable accounts, at 15.2% and 12.9%, respectively.

Within the consumer-controlled retirement accounts category, IRAs and Keogh accounts hold $19.1 trillion compared with DC plans’ $13.4 trillion, and the growth rate for those accounts is higher over 1-, 3-, 5- and 10-year periods.

“We are seeing signs that people are becoming more willing to leave money in their former employers’ retirement plans as more options for income planning enter the DC plan system,” Varas said. “But rollovers will remain strong, we suspect, as many people like the idea of consolidating their wealth in retirement.”

Data Support. Over half of near-retirees expect to move workplace savings elsewhere at retirement, while seven in 10 want both income protection and control of their investments, recent survey research from Allspring shows.

“Participants trust their employer, but many still plan to move their savings,” the report said. “What motivates participants to stay in plan? Lower costs, retirement-focused investment options and simple withdrawal flexibility are top reasons they’ll stay.”

To convert or not to convert? That is the question.

The next few months are a good time for clients to ask whether converting some of their pretax retirement assets to a Roth account makes sense, now that most people have a sense of what their total income for 2026 will be. It’s also a good time to educate them about how Roth conversions can affect other aspects of their financial plan, especially future required minimum distributions and what heirs will eventually inherit.

“For investors with larger traditional IRA or 401(k) balances, the most effective Roth conversion decisions come from projecting several years into the future,” said Heather Rivas, wealth advisor at River Wealth Advisors. “It also requires a discussion about whether choosing to pay additional taxes today will pay off in the future.”

Another Kind of Diversification

Most retirement investors are familiar with diversification across different asset classes, industries and geographic regions. Fewer are focused on tax diversification, Rivas said, which is where an advisor can shine.

“Converting to a Roth reduces the balance that will eventually be subject to RMDs,” Rivas said. “That can help retirees avoid being forced to recognize more taxable income than they need in a given year. IRAs are also a very tax-inefficient way to pass money to heirs.”

Any converted assets are counted as income, of course, so converting enough to fill a lower tax bracket may be attractive. However, converting additional dollars could push income into a substantially higher bracket or trigger other costs.

These dynamics make the period after a client retires but before they claim Social Security an opportune time to convert assets at comparatively low tax rates. Some additional considerations:

• A large conversion can increase modified adjusted gross income, potentially triggering higher Medicare premiums and surcharges.
• A conversion may be less attractive if a retiree lives in a relatively high-tax state today but expects to move to a lower-tax state later.

Triple Threat. Funding a Health Savings Account is another way to add tax diversification to the overall plan, said Kimberly Lankford, a longtime AARP contributor and current reporter for The Wall Street Journal Buy Side. The HSA complements other retirement accounts with its unique ability to pay for medical care on a tax-free basis, including Medicare premiums and out-of-pocket costs, she told Advisor Upside. Clients can even move money directly from a Roth or traditional IRA to their HSA through a one-time direct transfer called a qualified HSA funding distribution, though the amount is subject to the annual HSA contribution limit and other eligibility rules.