Dolly Parton and the Estate Plan That Couldn’t Prevent Everything

Dolly Parton apparently did a lot of estate planning right.

When she died in August, most of her estimated $450 million estate reportedly passed outside of public probate through trusts or business entities. At the beginning of the administration process, things went smoothly.

But a few weeks later, her estate administration landed in court.

The dispute involves Parton’s nephew, Bryan Seaver, who had worked for many years as part of her security operation and was a beneficiary under her estate plan. After Parton’s death, the company managing her affairs terminated his security company. Litigation and a temporary restraining order followed.

For estate planning purposes, who is right really doesn’t matter.

The interesting lesson is that Seaver apparently wore two hats: he was both a family member expecting an inheritance and a person earning his living through Dolly’s massive family business. That combination can be dangerous.

I see versions of this situation all the time in ordinary families. One child works in the family business. Another manages the rental property. A daughter keeps the books. A son maintains the cottage. Everyone gets along while Mom or Dad is alive because there is one person clearly in charge.

Then that person dies. Suddenly a trustee, successor manager, or sibling is making decisions, including decisions about somebody else’s paycheck and/or living arrangement.

That is where an estate plan can be perfectly valid and still leave plenty of room for a family fight.

A few planning lessons come out of the Parton story:

• Separate employment from inheritance. If a child or other relative works for the family business, there should be a clear employment or service agreement. Their right to inherit should be completely separate from their right to keep their job.
• Decide who has authority. The plan should make clear who controls the business after the founder dies and, importantly, who has the authority to hire or fire family members. The same holds true for things like the family cottage.
• Be careful with verbal promises. “I’ll always take care of you” or “you’ll always have a job here” can take on a very different meaning after someone dies. Important promises should be put in writing.
• Plan the transition. If a family member has access to bank accounts, computers, passwords, buildings, or confidential information, decide ahead of time how that access changes after death or retirement.

The larger lesson is one I see frequently in estate planning: documents can transfer assets, but they cannot automatically transfer authority, relationships, and family expectations.

Sometimes the most important estate-planning question isn’t simply, “Who gets what?”

It is also: “Who will be in charge—and what happens if someone in the family doesn’t like the answer?”

Fun Fact: My favorite Dolly Parton song is Mule Skinner Blues because of her powerful voice and fantastic yodel. That song became her first solo Top 10 country hit, reaching No. 3 on the Billboard country chart. It also earned her first solo Grammy nomination.

The Woods Are Full of Long Drivers (And Lousy Stocks)

One of my favorite quotes by Harvey Penick, the legendary golf teacher and author of Harvey Penick’s Little Red Book, is this: “The woods are full of long drivers.”

His point was that hitting the ball a long way can look impressive, but it doesn’t necessarily mean you are playing good golf.

I’m reminded of that from time to time, when I’m paired with a golfer who is absolutely swinging out of his shoes with the driver. Usually he’s a pretty big guy, and when he catches the ball, the sound is impressive. The problem is where the ball goes. One drive sails right. The next goes left. Then comes a worm burner that barely gets off the ground.

Eventually, usually somewhere toward the end of the round, he catches one perfectly. Three hundred yards, right down the middle of the fairway. And almost inevitably he says, “There it is.”

And I always think: Yes, there it is. One out of 17 or 18.

Maybe the lesson isn’t that the swing finally worked. Maybe the lesson is that it’s time to rethink the swing.

I review a lot of investment account statements, and one of the things that stops me in my tracks is seeing a bunch of individual stocks, sometimes 30 or more, often accompanied by frequent buying and selling as part of some type of short-term trading strategy.

Of course, some of those stocks are going to work spectacularly well. Just like that 300-yard drive, eventually you are going to catch one perfectly. But the real question isn’t whether you can point to one great winner. The question is whether the overall strategy consistently produces a better result.

Recent stock market numbers help illustrate the problem. Through late September, the S&P 500 was up more than 13% for 2026. You might assume that means most stocks were doing pretty well. In fact, only about 35% of the stocks in the S&P 500 were outperforming the index. Roughly 40% were down for the year, and approximately 25% had fallen 10% or more.

At the same time, a relatively small group of stocks produced enormous gains. That is an important characteristic of the stock market. Returns are not evenly distributed. A relatively small number of companies can account for a surprisingly large portion of the market’s overall return.

A study from Trivariate Research found that over the past 10 years, only about 23% of stocks in the S&P 500 actually beat the S&P 500 index itself. In other words, roughly three out of every four stocks failed to outperform the index.

That creates a difficult challenge if your investment strategy is built around selecting individual companies. You don’t just have to avoid the bad stocks. You have to make sure you own enough of the relatively small number that become extraordinary winners. And if the strategy involves frequent trading, you add another layer of difficulty: you have to decide which stocks to buy, when to buy them and, eventually, when to sell them.

Looking backward, that can seem easy. Of course we should have owned Apple, Microsoft, Nvidia, or Google. We know that because we already know how the story turned out. Knowing in advance which companies will become the great winners is considerably harder.

This is one reason I am such a believer in broad diversification. When you own a broad market index, you don’t have to predict which companies will ultimately become the great winners. You already own them.

Diversification isn’t simply about reducing risk. It is also about making sure you don’t miss the winners.

So, when I see an investment portfolio consisting of dozens of individual stocks accompanied by constant buying and selling, I sometimes think about Harvey Penick. Every once in a while, somebody is going to hit one 300 yards right down the middle. But that doesn’t necessarily mean the swing is working.

After all, the woods are full of long drivers — and lousy stocks.

Fun Fact: American golfers are estimated to lose roughly 300 million golf balls every year. That works out to more than 800,000 lost balls every day—in ponds, woods, deep rough, and whatever mysterious place that perfectly good ball disappeared to after you were absolutely certain you saw where it landed.

Four Signs Someone You Love (Including Yourself) May Need Help With Their Finances

As an estate planning attorney and a Certified Financial Planner™, almost all aspects of financial management are second nature to me. (Except using an ATM, which I haven’t done in over a decade.) Even with my experience, I’m confronted with the fact that everyone’s financial world is getting more complex all the time. That can make for some real challenges later in life.

Managing money involves a surprising number of little tasks like paying bills, reviewing statements, watching bank accounts, dealing with insurance, filing taxes and avoiding scams. Heck, even logging into an online account is getting more complex. As we age, these tasks can become harder and asking for help is not always the natural reaction. Here are some items to consider in identifying and addressing red flags that can signal someone’s need for help:

1. Bills are being missed—or paid twice.

An occasional mistake happens. But repeated late notices, overdrafts, duplicate payments or utilities nearly being shut off may mean someone is having trouble keeping everything straight.

Where to start: A family member may simply need to help organize bills or set up automatic payments. If that’s not enough, start by checking with the American Association of Daily Money Managers (AADMM) aadmm.com. You can locate a daily money management professional in your area from the website. They can help with organizing assets and paying bills. My clients who use them are very thankful.

2. Unusual confusion about money.

Someone who has always handled the finances suddenly can’t explain where accounts are located, how much money they have or why certain transactions occurred.

Where to start: This may be a good time to involve a trusted family member along with the person’s financial advisor, CPA, or attorney. This is also a good time to review who is named as successor trustee or agent under a financial power of attorney and talk with them about when and how they should be involved. Check for those documents. It might even be time to add a current co-trustee on a trust.

3. The appearance of strange purchases, withdrawals or gifts.

Large charitable donations, unexpected cash withdrawals, payments to unfamiliar people or sudden wire transfers deserve attention, particularly when they are out of character.

Where to start: If you suspect that a vulnerable adult is being financially exploited, Michigan Adult Protective Services can be reached 24 hours a day at 855-444-3911.

4. Money becoming a source of anxiety or avoidance.

Statements stay unopened. Financial conversations get pushed aside. Or you begin hearing, “I just don’t want to deal with this anymore.”

Where to start: Don’t wait until everything has to be taken over. Often the answer is simply providing some assistance with organizing accounts, monitoring transactions, paying bills or coordinating with professional advisors. I often meet with estate planning clients who have been independent for decades, but now realize it’s time to bring in a trusted family member or friend who can begin to assist in financial activities. The anxiety often drops substantially once a person acknowledges the need for help and identifies a trusted helper.

Independence is part of human nature, and asking for help can be difficult for many people. A delicate balance of respect and probing can help to fully understand the situation.

Don’t wait for a major problem. Start exploring options as early as possible.

Fun Fact: Fall is here, and apple cider is abundant. Yates Cider Mill in Rochester Hills is Michigan’s oldest cider mill. The land was purchased in 1863, while Abraham Lincoln was president and the mill was pressing cider by 1876. Its water-powered turbine, installed in 1894, still powers the cider press today.