Free education from Joel Bernstein, retired attorney

 I'm Joel Bernstein. I spent thirty-two years practicing estate planning law in Massachusetts before retiring in early 2025. I can't take clients anymore, but I still care about helping families avoid expensive mistakes.
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This page explains when Massachusetts families need estate planning help and what happens when you skip it. Then I'll connect you with an excellent attorney who can actually do the legal work. No obligation. No pressure. Just honest information and a solid referral when you're ready.

The Two Million Dollar Surprise

Most people think estate planning is only for wealthy families. That's wrong in Massachusetts because of how our state tax works compared to federal tax. The federal estate tax exemption is fifteen million dollars per person. Massachusetts starts taxing at just two million dollars. That's a huge difference that catches middle-class families completely off guard.

Here's how quickly two million adds up in Greater Boston. Your house in Newton or Lexington is worth nine hundred thousand dollars. You and your spouse have retirement accounts totaling one point three million. You carry six hundred thousand in life insurance to protect your family if something happens. Add those numbers together and you get two point eight million. You're eight hundred thousand over the Massachusetts threshold even though you don't feel wealthy.
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Massachusetts will tax that eight hundred thousand at roughly ten percent. Your family pays eighty thousand dollars that proper planning could have avoided. That's a new car. That's two years of college tuition. That's money your children should inherit instead of sending to the state.

Count everything when calculating your estate value. Your house counts. All retirement accounts count. Life insurance death benefits count. Investment accounts count. Many families forget about life insurance and get shocked when they realize they're over two million.

Who Raises Your Children

If you have children under eighteen, choosing legal guardians is the most important decision you'll make in estate planning. Period. Nothing else comes close to this level of importance. Without choosing guardians in your will, a Massachusetts probate court judge decides who raises your kids if something happens to you and your spouse.

The judge doesn't know your family. The judge doesn't know that your brother would be a terrible choice because of his drinking. The judge doesn't know that your sister-in-law has strong parenting skills but completely different values about education and religion. The judge hears from relatives who want custody, reviews some basic background checks, and makes a decision based on limited information.

Sometimes the judge picks relatives you would never choose. Sometimes multiple relatives fight for custody and your children watch family members battle in court. Sometimes the judge appoints a temporary guardian while sorting out the permanent situation, which means your children move twice and deal with uncertainty during the worst time of their lives.

Pick guardians now, even if choosing feels impossible. 

Think about who shares your values about education, religion, and discipline. Think about who has the energy to raise children. Think about who your kids already love and trust. Choose a first choice and a backup choice in case your first choice can't serve. Then talk to these people and make sure they'll accept this enormous responsibility.

The Probate Court Trap

Probate is the legal process where a court supervises distribution of your assets after you die. In Massachusetts, probate takes a minimum of six to eighteen months. During that time, your bank accounts freeze. Your family can't access money to pay the mortgage or property taxes. They can't sell your house without court permission. Everything waits for the court to process paperwork and approve each step.

Probate costs add up quickly. Court filing fees, attorney fees, and executor fees typically total fifteen thousand to fifty thousand dollars for estates over five hundred thousand. That's money coming out of your children's inheritance to pay lawyers and court costs. None of this money goes to your family. It all goes to the legal system for supervising something that proper planning would have handled privately.

Living trusts avoid probate completely in Massachusetts. When you create and properly fund a living trust, your assets pass directly to your beneficiaries without court involvement. Your family gets immediate access to funds. They can pay bills and handle financial matters right away. No waiting for court approval. No unnecessary legal fees. No public record of what you owned and who got what.
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The Beneficiary Disaster

Your retirement accounts and life insurance policies have beneficiary designations that determine who gets the money when you die. These beneficiary designations override your will completely. It doesn't matter what your will says if your beneficiary forms say something different. The beneficiary forms always win.

I saw this disaster repeatedly during my practice. Someone gets divorced and creates a new will leaving everything to their new spouse and children. But they forget to update the beneficiary designation on their old 401k from a previous job. That 401k still lists their ex-spouse as beneficiary. When they die, the ex-spouse gets four hundred thousand dollars even though the will clearly stated everything should go to the current spouse. The current spouse has to fight in court, which is expensive and often unsuccessful.
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Check all your beneficiary designations right now. Every retirement account from every job you've ever had. Every life insurance policy including that small policy through your employer. Every bank account with payable-on-death provisions. Make sure the names listed match your current wishes. Update anything that's wrong. Name contingent beneficiaries in case your primary beneficiary dies before you.

​Old Plans That Don't Work Anymore

Massachusetts estate planning laws change regularly. If your will or trust is more than three years old, there's a good chance it has gaps that create problems under current law. Documents from 2021 often lack provisions for digital assets like cryptocurrency or online accounts. They might use outdated tax planning language that doesn't work with current Massachusetts estate tax rules. They might not address pandemic-related concerns about healthcare decision-making.

Even if the laws haven't changed, your life probably has. Maybe you've had another child since creating your estate plan. Maybe you've gotten divorced and remarried. Maybe your parents have died so you need different backup guardians for your kids. Maybe your house value has appreciated significantly and pushed you over the two million dollar Massachusetts tax threshold. All of these changes mean your old plan might not work the way you think it does.
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Review your estate plan every three years minimum. Also review immediately after major life changes like births, deaths, divorces, or significant changes in asset values. Laws change and life changes. Your estate plan needs to keep pace with both.