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In this episode, Ted Gudorf shares crucial estate planning insights, focusing on assets that should not be placed in a living trust and how to properly manage them to avoid costly mistakes. Learn the key steps to protect your wealth and ensure your estate plan works when it matters most.
The Estate Planning Mistakes That Can Trigger Massive Taxes, Probate Delays, and Costly Family Problems
A living trust is one of the most powerful estate planning tools available—but only when it's used correctly.
Unfortunately, many people hear the same piece of advice: "Put everything into your trust." While that sounds simple, it's actually one of the most expensive estate planning mistakes you can make.
Certain assets were never designed to be owned by a revocable living trust. Moving them into your trust—or failing to structure them correctly—can trigger unnecessary taxes, create probate issues, jeopardize business interests, or delay access to money your family needs.
The good news is that these mistakes are completely avoidable when you understand which assets belong outside your trust and how they should be coordinated with the rest of your estate plan.
Here are five assets that generally should not be placed into your living trust—and why they deserve special attention.
1. Retirement Accounts Can Create an Unexpected Tax Disaster
Retirement accounts are often the largest tax-deferred assets people own. Because of that, many assume they should be transferred into their trust.
In reality, doing so can have serious tax consequences.
Traditional IRAs, 401(k)s, and similar retirement accounts operate under strict IRS ownership rules. Attempting to transfer ownership into a living trust can cause the IRS to treat the transaction as a taxable distribution rather than a simple transfer.
That means the entire balance could become taxable income in a single year.
For larger retirement accounts, the resulting tax bill can easily reach six figures.
Instead of changing ownership, retirement accounts are generally coordinated through properly updated beneficiary designations. Those beneficiary forms—not your will or trust—typically determine who receives these assets.
For larger retirement accounts, specialized trust strategies may be appropriate in certain circumstances. These are not the same as a standard revocable living trust and require careful planning with an experienced estate planning attorney.
The key takeaway is simple: retirement accounts require their own planning strategy.
2. Life Insurance Doesn't Follow Your Trust
Many people spend considerable time creating a comprehensive estate plan, yet overlook one simple document that may override everything else.
The beneficiary designation on a life insurance policy controls who receives the proceeds.
If that form is outdated, names a deceased beneficiary, or no longer reflects your wishes, your family could face unnecessary delays, legal expenses, and even probate.
This is especially important because beneficiary forms are often completed decades before someone updates their estate plan.
Even families with well-designed trusts can experience major complications if those beneficiary designations are never reviewed.
For larger estates, life insurance ownership can also affect potential estate tax exposure. In some situations, an Irrevocable Life Insurance Trust (ILIT) may be considered to help address those concerns.
While that strategy isn't appropriate for everyone, reviewing your beneficiary designations is something virtually every policy owner should do.
3. Business Interests Require Special Planning
Business owners face an entirely different set of estate planning challenges.
Whether you own an S Corporation, LLC, or closely held business, transferring ownership into a living trust without proper planning can create unexpected legal and tax consequences.
For S Corporations, trust language matters.
If the trust isn't drafted to satisfy IRS requirements, the corporation's tax status may be affected—potentially leading to significant administrative and tax complications.
LLCs present their own challenges.
Many operating agreements contain restrictions on ownership transfers. Some require approval from other members before any ownership interest can be transferred into a trust.
Ignoring those provisions can lead to disputes that could have been avoided with proper planning.
Business succession planning is often one of the most technically complex areas of estate planning, making professional guidance especially valuable.
4. Health Savings Accounts Lose Their Special Tax Advantages
Health Savings Accounts (HSAs) receive some of the most favorable tax treatment available.
Contributions may be tax deductible.
Growth is tax deferred.
Qualified medical withdrawals are tax free.
Those valuable benefits exist because the account belongs to an individual—not a trust.
Improper ownership or beneficiary designations can create unnecessary income tax consequences after death.
Fortunately, this is often an easy issue to address.
For married couples, naming a spouse as the primary beneficiary typically allows the HSA's tax advantages to continue.
A quick review of your beneficiary designation today may prevent significant tax consequences for your family later.
5. Your 529 Plan May Already Have a Better Solution
Many grandparents and parents assume their education savings plans should be transferred into their living trust.
However, 529 plans don't all operate the same way.
Some plans permit trust ownership.
Others do not.
Fortunately, many plans provide another solution altogether: the successor owner designation.
This feature allows you to name the person—or, in some cases, a trust—that automatically takes control of the account if something happens to you.
That means educational funds can remain available without unnecessary delays, helping students continue paying tuition and qualified education expenses when they need access most.
If you have multiple 529 plans, each one should be reviewed individually because every plan follows its own rules.
Why "Putting Everything in the Trust" Isn't Always the Right Advice
One of the biggest misconceptions in estate planning is that every asset should be retitled into a living trust.
The truth is more nuanced.
A well-designed estate plan doesn't treat every asset the same.
Instead, it coordinates each asset according to the specific tax rules, ownership requirements, beneficiary designations, and legal protections that apply.
That's what allows your estate plan to function efficiently when your family needs it most.
The Bigger Picture
Knowing what doesn't belong in your living trust is only half of successful estate planning.
The other half is making sure the assets that should be in your trust are properly titled and funded.
An unfunded trust—even one that's expertly drafted—may not accomplish the goals you intended.
That's why reviewing both your trust documents and your asset ownership on a regular basis is one of the most important steps you can take to protect your family, preserve your legacy, and minimize unnecessary complications.
Estate planning is never about checking a box.
It's about making sure every piece of your financial life works together exactly the way you intended.
Conclusion
A living trust remains one of the most effective estate planning tools available, but only when it's coordinated with the unique rules governing each type of asset.
Retirement accounts, life insurance, certain business interests, Health Savings Accounts, and many 529 plans all require specialized handling. Treating them like every other asset can create unintended tax consequences, probate delays, or legal complications that could have been avoided.
By reviewing these assets now—and ensuring they're integrated into a comprehensive estate plan—you can help protect your wealth, simplify the administration of your estate, and leave your family with clarity instead of confusion.
Transcript: Prefer to Read — Click to Open
Ted (00:00.086)
A Living Trust is one of the smartest tools in estate planning, but putting the wrong assets inside it can create taxes, headaches, and problems for your family. By the end of this video, you’ll know exactly which assets should never go into your living trust and why. I’m Ted Gudorf, an attorney here in Dayton, Ohio for the last 30 years. My team and I have helped families protect their wealth.
Preserve their legacy and pass on what matters most. The first asset is the one that produces the largest single tax bill I see in estate planning, and it comes from people doing exactly what they were told to do. A client came to our office after doing her own research and deciding she wanted everything in her trust. She had already contacted several financial institutions to begin the transfers. She had not reached her IRA yet.
Her daughter suggested she check with an attorney first. When I heard what she was planning, I immediately stopped her. If she had made that call to her IRA custodian, she would have owed income taxes on four hundred thousand dollars before the year ended. The IRS does not treat moving your IRA into a living trust as a transfer. They call it a withdrawal.
Every dollar in that account becomes ordinary income the year that the change takes place. On a four hundred thousand dollar IRA, you’re looking at $150,000 or more in federal and state income taxes, depending upon where you live. In California, that number can reach $200,000. You can’t undo it once it happens. Remember, your IRA is
four hundred one K, four hundred three B all exist under strict federal ownership rules. Congress allows those accounts to grow tax deferred or tax free only because the individual account holder follows those rules. The moment ownership transfers to a trust, those rules break. The account loses its qualified status and the IRS taxes the full balance that year.
Ted (02:25.836)
What you do instead is straightforward. Keep those retirement accounts in your individual name. Then contact the institution holding them and ask one question who is listed as my beneficiary? That call takes fifteen minutes, and it may be the single most important step in your entire estate plan. If the beneficiary is outdated, if it names a former spouse or a parent
Who has already passed away, that money goes to the wrong person, regardless of what your trust or will says. For larger accounts, meaning a single IRA of $500,000 or more going to one person, there are specialized trust structures built to receive inherited retirement accounts at death without triggering an immediate tax event. These are not.
Your living trust, they spread distributions over time and significantly reduce what the beneficiary owes. One client whose child stood to inherit a $1.2 million IRA, use this structure to spread that tax burden out over a decade rather than absorbing it all at once. Ask your estate planning attorney whether that structure makes sense for your situation. Retirement accounts stay out of the trust.
You manage them through the beneficiary designation form alone. Now you know why retirement accounts stay in your own name. But the next asset is one where I’ve watched families have an attorney’s office thinking everything is handled, and then discover years later that it was not. The beneficiary form on your policy is what controls where that money goes, not your trust, not your will.
The form you filled out the day you bought the life insurance policy controls. One person had a $200,000 life insurance policy. Her trust was fully funded. Her estate plan was clean, but the beneficiary on her policy was still her mother, who had died two years earlier. No contingent beneficiary was ever listed. The death benefit went into probate. The process
Ted (04:53.166)
Took 18 months. It cost the family twelve thousand dollars in legal fees just to resolve. Every dollar of that was preventable. A ten minute phone call to update that beneficiary form would have solved the entire thing. If your beneficiary form names someone who has died or someone you no longer intend to inherit, the money goes the wrong direction. Full stop. There is a second issue for larger estates.
If you own a life insurance policy in your own name and your estate exceeds the federal estate tax exemption, the death benefit gets added to your taxable estate. Now, the federal exemption for 2026 sits at $15 million per person. But that number has changed before and it will change again. If you carry a $5 million policy,
And your estate is already at twelve million dollars, you are above the line and the tax bill can be significant. So for those situations, there is a tool called an irrevocable life insurance trust. In that case, the trust owns the policy rather than you. The death benefit stays outside your taxable estate at death because it’s payable to the trust.
For one client, this structure saved the family eight hundred thousand dollars in estate taxes. It is not the right move for everyone. For most families, simply updating the beneficiary designation is the step that changes everything. Your action step. Call your life insurance company today or your agent. Ask who is the primary beneficiary? Ask who is the contingent beneficiary.
Write both names down and compare them to your current estate plan. If they do not match, fix it now. So your retirement accounts are handled and your life insurance beneficiaries are current. But the next asset catches business owners completely off guard and the damage does not show up in your estate plan. It shows up on your tax return. If you own shares in an S corporation,
Ted (07:20.886)
And you transfer those shares into a living trust that does not contain specific S corporation language, the company could lose its S status the day that the transfer is recorded. No warning, no grace period. Here is why that matters. An S corporation pays taxes once at the owner’s level. The profits pass through directly to you.
And you pay income tax on your share. Now, a C corporation pays taxes twice. The company pays at the corporate level first, and then you pay again when money comes out as a dividend. The S corporation structure is a real advantage for most business owners, and it comes with federal rules that strictly govern who can hold those shares. Not every trust qualifies.
If your trust document does not contain the right language, the company converts to a C corporation automatically. Restoring S Corp status requires an IRS relief request, amended returns, and legal work that costs far more than the estate plan was built to protect. Beyond S corporations,
Most limited liability companies have operating agreements that control who can own a membership interest. Some require unanimous approval from every member before a transfer takes place. Some even prohibit transfers without written consent. So if you transfer your LLC membership interest into a trust without reading that operating agreement, the other members have the right to reject the transfer.
You could walk into a legal dispute over something a 30-minute review would have prevented. Before any business interest goes into a trust, do two things. First, give your estate planning attorney the operating agreement or shareholder agreement so they can confirm the transfer is permitted. Second, if you have S corporation shares, ask specifically.
Ted (09:38.456)
Whether your trust document contains the language required to hold them without triggering a conversion. Do not assume it does. Business interests are the most technically involved issue we have covered. Now, the next one is almost the opposite. It looks simple on the surface, which is exactly why people get it wrong. Health savings accounts carry some of the best.
best tax treatment available anywhere in the tax code. Money goes in tax-free, it grows tax-free, it comes out tax-free for medical expenses. That triple advantage exists only because the account belongs to you as an individual. Transfer ownership to a living trust, and that status disappears. The IRS no longer treats it
As an HSA. It becomes a standard taxable account, and the years of tax-free growth no longer apply. The situation at death is where the real problem shows up. If your spouse inherits your HSA, they roll it into their own account and every tax advantage carries forward. But if your living trust is named as the beneficiary,
The full value of the account becomes taxable income in the year you pass away. On an HSA with eighty or a hundred thousand dollars saved, that is a real tax bill your family absorbs all at once. A couple we worked with had contributed to their HSAs for eighteen years. Between the two accounts they had just over $140,000 saved. Both accounts listed their revocable trust as beneficiary.
Because someone had told them to make the trust the beneficiary of everything. We changed both designations. The husband named his wife as primary, the wife named her husband as primary, both listed their adult children as contingent beneficiaries. That one change protected all hundred forty thousand dollars from an immediate tax event at the first death. Your action step.
Ted (11:57.73)
Contact the institution holding your HSA. Ask who the current beneficiary is. If it is your trust, change it to your spouse’s primary and your children as contingent. This is one of the most straightforward fixes in estate planning and one of the least addressed. Your HSA is now handled, but there is one more account that grandparents and parents have been building for years.
And the mistake here does not show up as a tax bill right away. It shows up as a frozen account the month a grandchild needs to pay tuition. A 529 plan works like this. You are the account owner. Your child or grandchild is the beneficiary. The money grows tax free and comes out tax free for qualified education expenses. The word qualified is what matters.
Some plans, for instance, the Ohio College Advantage Plan, allow a trust to be the owner of a 529 plan, but some 529 plans do not allow a trust to serve as the account owner. The plan administrator instead will reject the transfer, and you are back where you started, except now you have created paperwork that accomplished nothing.
What most families do not know is that five twenty nine plants have a built-in solution for this problem. It is called a successor owner designation. You name a person or trust to step in and take over the account if something happens to you. The person or the trust becomes the new owner immediately, can change the beneficiary if needed and
And the full tax-free status of the account stays intact. No probate required. We worked with grandparents who had set up a $529 for their four grandchildren with balances ranging from $40,000 to $85,000 each. None of the accounts had a successor owner name. When the grandfather passed away, all four accounts were frozen while the estate went through probate.
Ted (14:17.048)
Tuition payments were delayed for months. One grandchild had to take out a short-term loan to cover a semester while the legal process ran its course. None of that needed to happen. So contact your 529 plan administrator and ask whether a successor owner designation is available. Ask if your trust can be either a current owner or successor owner.
It depends upon your plan. But name one today. If you have accounts across multiple plants, check each and every one of them separately because each plan handles this differently. This one step ensures the account transfers to the right person immediately and the money stays available for education exactly as you intended.
Now you know the five assets that belong outside your living trust: retirement accounts, life insurance, certain business interests, health savings account, and perhaps a 529 plan each come with their own set of rules. Keeping them out is not a workaround. It is what a correctly built estate plan looks like. Now, the next question most people ask is.
What does belong in the trust and how do I get it there? That is exactly what the next video answers. Because here is what most families never get around to. And it is where estate plans fall apart. Knowing what to keep out is only half the plan. The other half is knowing what belongs inside the trust and how to get it into the trust correctly. A trust that is not
Properly funded is a trust that does not work when your family needs it to work. I want you to click on seven key trust assets and how to effectively fund them into your trust to see the full process step by step. The mistake in step four surprises almost every client we work with.
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