Why Doing Retirement Yourself Gets Harder as Wealth Grows

Christine Benz has spent her career at Morningstar studying how people invest and retire. She isn’t a financial advisor herself. She recently published a piece on three retirement topics she’s changed her mind about, and one of them was whether people heading into retirement need help.

She used to think they mostly didn’t. Her reasoning was fair: building a decent portfolio of mutual funds is not that hard, so why pay a fee for something you could do on a Saturday morning? She still meets people who pull it off, though she also points out that a 17-year bull market has covered up a lot of mistakes.

Portfolio Construction Is the Easy Part

What she says she underrated is how small a piece of the work portfolio construction really is. In her view, advisors help people put numbers to goals they’ve only ever said out loud, help them stay invested in the years when everything feels wrong, and look for ways to manage the tax bill along the way.

Spending It Down Is Harder Than Building It Up

Then she gets into decumulation. Spending a portfolio down is harder than building one up. She calls it “devilishly complicated” and suggests that anyone who gets it right on their own all the way through retirement is probably an outlier.

The 4% guideline is a starting point, not a plan. The real questions are which accounts you draw from, in what order, and what that sequence does to your tax bill over the next 20 years. Add when to file for Social Security, how Medicare premium surcharges work, and how you plan to pay for long-term care, and the list of decisions gets long quickly.

Someone Else Needs to Know Where Everything Is

The reason she gives for hiring someone later in life that I almost never hear people bring up is this: somebody besides you needs to know what you own and where it’s held, and somebody needs to be able to step in if you get sick or your memory starts to slip.

When Wealth Adds Complexity

Everything above describes a fairly ordinary retirement: one house, a 401(k), an IRA, maybe a taxable account.

Now add significant wealth. An estate large enough to owe tax. A business you plan to sell in the next three years. Concentrated stock you’ve held since the 1990s. Trusts drafted before your kids were adults. Charitable intent you’ve never formalized. Each of those is its own discipline, and they refuse to stay in separate boxes. The timing of a business sale changes your tax picture, which changes how much you may want to convert to a Roth, which changes what lands in your estate, which changes what your children inherit and in what form. Retirement planning is complicated on its own. Layer significant wealth, estate exposure, a liquidity event, and advanced tax planning on top of it, and the complexity compounds rather than adds.

The Estate Math Catches People Off Guard

The One Big Beautiful Bill Act, signed in July 2025, set the federal estate tax exemption at $15 million per person and $30 million per married couple starting in 2026, indexed for inflation and with no scheduled sunset. That sounds like plenty right up until your balance sheet clears it.

The federal number is also only half the question. According to one law firm’s analysis, a New York married couple that dies in 2026 with just under $30 million would owe nothing in federal estate tax but nearly $4.3 million to the state.

The Hardest Problems Aren’t Math

The math isn’t what keeps these families up at night. In a 2023 survey of households with $25 million or more, CEG Insights found that 77.5% worry their heirs will waste what they pass down. No withdrawal sequence solves that one. It usually takes years of conversation, some structure, and bringing the next generation into the room a lot earlier than most families are comfortable with.

The same research found that 80.3% of these families want their advisor, accountant, and attorney actually talking to each other. That tracks with what I see. The expensive problems at this level tend to live in the seams between professionals, and often nobody is watching those seams unless someone has been given the job.

Before You Decide to Go It Alone

When people ask Benz for one piece of retirement advice, her answer is “get some help.” In my view, that matters even more as the balance sheet grows. Being good at building wealth is a different skill from being good at unwinding it, and most people have never had a reason to practice the second one. You only retire once.

If you’re a few years out and have been assuming you’ll handle it yourself, read her piece before you decide.

Sources

Christine Benz quotes, the 17-year bull market, “devilishly complicated,” the outlier point, and “get some help”: Christine Benz, “I Thought I Had These 3 Retirement Topics Figured Out. Here’s Why I Changed My Mind,” Morningstar, Aug. 24, 2026. https://www.morningstar.com/retirement/second-thought-3-retirement-topics-ive-changed-my-mind-about

77.5% worry their heirs will waste what they pass down: CEG Insights, The $25 Million-Plus Advisor Playbook, 2023 (N=164), as reported in Michael Kitces and John Bowen, “The 3 Concerns Keeping $25M+ Families Up at Night,” Kitces.com, Aug. 2025. https://www.kitces.com/blog/ultra-high-net-worth-family-concerns-25m-advisor-services-upmarket/

80.3% want their advisor, accountant, and attorney talking to each other: CEG Insights, The $25 Million-Plus Advisor Playbook, 2023 (N=165), same Kitces/Bowen source as above.

$15 million per person and $30 million per couple: One Big Beautiful Bill Act, signed July 4, 2025, effective Jan. 1, 2026, indexed for inflation. Confirmed for 2026 in Morgan Lewis, “IRS Announces Increased Gift and Estate Tax Exemption Amounts for 2026,” Oct. 2025. https://www.morganlewis.com/pubs/2025/10/irs-announces-increased-gift-and-estate-tax-exemption-amounts-for-2026

New York couple with just under $30 million owing nearly $4.3 million in state estate tax: Venable LLP, “Estate Planning in the OBBBA Era: What the $15 Million Exemption Means for You,” Sept. 2025. https://www.venable.com/insights/publications/2025/09/estate-planning-in-the-obbba-era-what-the-15