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Estate Planning: Will You Trust a Trust, or Will Your Will with a Will?

Estate Planning: Will You Trust a Trust, or Will Your Will with a Will?

March 03, 2026

If you’ve ever sat down to think about your "estate," your mind might go straight to images of high-back leather chairs and dusty law books. But in reality, your estate is just your life’s work—your home, your savings, and the legacy you want to leave for the people you love. 

The big question is: What happens to it all when you’re gone?

Surprisingly, only about 32% of American adults have a written plan as of 2024. In a recent webinar, Sean Hendricks—an Estate Planning Attorney and Fiduciary Financial Planner at Hendricks Wealth & Estate Management—dived into why that’s a risky move and how you can take control of your future.

Here is a look at the three most common paths people take, including some great "real-world" insights from the live Q&A session.

The Three Paths You Can Take

Sean breaks down estate planning into three simple categories. Depending on which one you choose (or don't choose), the experience for your family will be very different.

1. The "No Plan" Plan (Intestate Succession)

This is the default if you do nothing. If you pass away without a will or trust, the law steps in to distribute your stuff. Many people assume everything automatically goes to their spouse, but that isn't always true. In Illinois, the law often splits assets between a surviving spouse and children. Essentially, if you don't make a plan, the state has one for you—and you might not like it.

2. The Last Will and Testament

A will is a legal document that provides instructions on how to divide your property and, most importantly, names guardians for minor children.

  • The Pros: It’s usually the most affordable way to get started. It is also the only document that can legally designate a guardian for children under 18.

  • The Cons: Wills almost always have to go through probate. This is a public court process that can take 12 to 18 months—and it can be quite expensive.

3. The Living Trust

A trust creates a separate legal entity that holds your property for your benefit while you’re alive and for your heirs later.

  • The Pros: Trusts are built to bypass the courthouse. They are private, efficient, and usually much faster than a will. They also allow for more advanced "beneficiary planning" to help save on taxes.

  • The Cons: They take a bit more work upfront. You have to "fund" the trust, which means retitling your house or bank accounts into the name of the trust.

Real Questions from the Audience (The "Outtakes")

During the webinar, Sean answered some excellent questions that clarify the "grey areas" of estate planning:

  • "Does an old trust from 20 years ago still work?" As long as you were the one who created it, yes! Trusts are meant to be flexible. If your life has changed, it’s very easy to amend the document to reflect your life right now.

  • "If my trust is empty, does it still exist?" Sean compares an unfunded trust to an "empty boat". It’s there waiting for you to load it up. However, if you pass away and the boat is still empty, it effectively ceases to exist.

  • "Do I need a lawyer to put my house in a trust?" While you could technically try to file a deed yourself, Sean generally doesn't recommend it. Every county has different rules, and it can be a bit daunting.

It’s More Than Just Your "Stuff"

One point Sean makes very clear is that a complete estate plan isn’t just about what happens after you die—it’s about protecting you while you're still here. No plan is complete without these critical documents:

  • Healthcare Power of Attorney: Picking someone to make medical decisions if you’re ever unable to speak for yourself.

  • Property (Financial) Power of Attorney: Giving someone authority to handle your finances—like paying your mortgage—if you’re incapacitated.

  • Living Will: Written instructions for your end-of-life care, ensuring your wishes are followed.

Which One Is Right for You?

How do you choose? Sean offers some practical rules of thumb:

  • Choose a Will if: You’re in the "asset gathering" stage of life. If you’re young or have minor children, a will is a non-negotiable for naming guardian.

  • Choose a Trust if: You’ve accumulated a home and significant savings. If you want to make sure your family can avoid the stress and public nature of probate court, a trust is likely the better fit.

Why the "Fiduciary" Part Matters

What makes Sean Hendricks' approach unique is that he wears two hats: he’s an attorney and a financial planner.

He believes your estate plan and your retirement plan should be "rowing in the same direction". It doesn’t do much good to have a perfect trust if your life insurance or 401(k) beneficiaries aren't coordinated with it. By looking at both sides of the coin, you can protect your assets and ensure your legacy goes exactly where you intended.

Don't Leave Your Family Guessing

At the end of the day, estate planning is a gift to your family. It prevents disputes and provides clarity during an emotional time. As Sean says, "If you don't make a plan, nobody knows what you really wanted".

If you have questions or want to start building your own plan, reach out to the team at Hendricks Wealth & Estate Management at the email, phone numbers or website below.