As an estate-planning professional who uses a multidisciplinary approach—legal, tax, financial, insurance, long-term care, and funeral planning—I’ve seen a lot. Most of it is good. Some of it is excellent. But there are three things in this field that absolutely drive me crazy because they hurt families, cost them money, and create heartache that could have been prevented with proper guidance.
Let me walk you through my three biggest pet peeves—and why they matter to you.
1. The U.S. Post Office
I won’t go into detail here. Trust me, it’s a story best told over the phone when I can speak freely. But I’ll simply say: when it comes to delivering your most important legal and financial documents, relying on the Post Office introduces layers of uncertainty that you do NOT want in the estate-planning process. Call me sometime—I’ll tell you exactly why this makes my list.
2. Lawyers Who Don’t Finish the Job
I can’t tell you how many families come to me thinking they “have an estate plan” because years ago they called a local attorney who drafted a will and maybe a couple of powers of attorney. And that’s it.
This is a recipe for disaster.
Let me explain exactly how this plays out:
A tragedy happens. A parent passes away. The adult children find that will, dust it off, and naturally call the attorney who prepared it. That attorney—who did nothing wrong ethically or legally, by the way—says the dreaded words:
“Well… I guess we’ll have to go to probate.”
And suddenly, a family with modest means is facing probate costs that can run up to 12% of the probatable estate. For many families, that’s thousands—sometimes tens of thousands—of dollars.
Here’s the real problem:
If that attorney didn’t protect you from the simple stuff, like probate, they absolutely did NOT protect you from the hard stuff—like lawsuits, nursing home exposure, Medicaid spend-down, tax traps, or the SECURE Act.
I call this the sin of omission.
Not immoral. Not unethical. But incomplete.
And guess what?
Probate is a multi-year revenue source for that attorney—something that could have been avoided entirely if the job had been done right.
3. Financial Planners Who Don’t Finish the Job
This one hits close to home, because the majority of financial advisors proudly call themselves “retirement specialists”… while treating 55-, 65-, and 75-year-olds as if they’re still in their 20s and 40s.
Retirement is a completely different game with completely different rules.
Let me make a bold statement:
Rate of return is the FOURTH most important thing in retirement planning.
You read that right. Fourth.
So what are the first three?
#1 – Don’t lose money.
You spent 40 years building your nest egg. The worst thing you can do is suffer a significant loss in the fourth quarter of life.
#2 – Have a complete tax plan.
Taxes are going up. The SECURE Act gutted the traditional stretch IRA. Most people are sitting on a tax bomb and don’t even realize it.
#3 – Have a nursing home and long-term care plan.
According to U.S. News & World Report, 70% of people age 65+ will need some form of care. Whether that’s short-term, long-term, or assisted living, the financial consequences can be devastating.
These are big-kid problems that require big-kid solutions. Yet most financial advisors still plan as if their retired clients are 45 years old. They aren’t. And the advice must evolve accordingly.
The Real Problem: People Think They’re Protected—Until They Aren’t
My three pet peeves all stem from the same root issue:
People not finishing the job.
Attorneys who stop at documents.
Advisors who stop at investments.
Professionals who leave enormous gaps.
Families who think they are protected… until something bad happens and they learn the truth the hard way.
The result?
A process that becomes expensive, public, taxable, stressful, and entirely avoidable.
Either You Have a Plan—Or You’re Part of Someone Else’s Plan
If you care about your assets, your spouse, your children, and your legacy…
Get a complete plan.
Not half a plan.
Not a stack of documents.
A real, coordinated, multidisciplinary plan created by professionals who actually finish the job.
Your family deserves nothing less.
