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Education of an Executrix: A “When-I’m-Gone” Plan is a Lasting Love Note

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You've no doubt heard the phrase that the only certainties are "death and taxes." But we rarely talk about how death doesn't get anyone off the hook for filing taxes. The death of a loved one leaves us with stacks of paperwork, frustration, and, in many cases, a team of professionals who gladly bill the estate $400 per hour to clean up those untidy stacks. 

Even when a loved one has a Will and Trust completed before their death, an estate's financial and tax challenges can drag on us like heavy weights while grieving. 

I use the term ‘taxing’ with two meanings in my world: 

  1. The administrative responsibility of paying taxes to Federal & State entities.
  2. The  taxing emotional, physical, and mental work of managing a person's wishes for years after they have passed. 

Managing estate logistics can delay the process of personal healing due to the necessary details that need to be handled.

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How do I know this, and why do I say it so bluntly?

Like many others on our team, my commitment to Caregiven's purpose is fueled by lessons learned painfully and alone. Over the past four years, I managed and cared for my sister, mom, and dad while each battled and eventually succumbed to unrelated cancers. I wore every hat imaginable and took on many roles -- all of which were difficult with the intense complications of grief and sadness. After each of these people I loved died, a HUGE blind spot became apparent: I will be managing their legacies for many years to come.

My sister, mother, and father gave me the roles of guardian, executrix, and trustee because I was the youngest in the family and have many years of business experience. I soon learned that the responsibilities required to manage their wishes as expressed in their words in Trusts* are all multi-year, long-tail commitments because their legacies include children, lines of succession, and people with special needs.

All in all, for 2021, I'm managing five trusts tied to my family's legacy. Each trust carries unique, intricate tax responsibility and rules.  Translation:  Lots of tax forms and lingo.

The commitment required by this role is why I refuse to sugarcoat it: the roles of Executrix and Trustee require a LOT of emotional, administrative, and even physical work. Choose these people wisely. But do choose them as part of your plan.  

Let’s start with a conversation starter:  

Why plan for your stuff after your death?

Because you love people or a charity and want to take care of them after you die. If you die without a Will*, your state has the power to manage your asset distribution (stuff) according to specific state rules. 

Really? The state? They decide who gets what?                   


Nobody wants that. As a labor and employment lawyer once said, "The only person guaranteed to benefit from an estate contest is the lawyer."

So, if you take nothing else from this post, please let it be to:

Make a plan for the people you love.  Do it for them. 

I'll say it again: make a plan. It's easier to plan while you are happy and healthy. Sure, you'll need to regularly revisit a Will and Trust (I recommend at least every five years to keep up with your life changes), but the first one gives you a good foundation.

Loving the people in your life means thoughtfully creating a plan for your belongings, investments, and assets when you die. Don’t leave the important things to chance or leave a mess for others to sort out.  This is one part of dying that can be thought about way in advance and is an expression of compassion for those you care about. People are attached to memories associated with belongings, and those who love you can swirl into sentiment or resentment if you don’t spell out your intentions.  

Be clear. Be compassionate. Hell, be funny. Just make a plan. 

Is what I do as an Executrix and Trustee a lot of work? Abso-freakin-lutely. 

I say it again, five Trusts, each with their own administrative and tax Ids. Every tax form, investment, report, and conversation about their wishes requires serious emotional and intellectual effort. Sometimes managing this love legacy is intense for me. 

BUT, This is the commitment I made when I agreed to be their estates' Executrix and  Trustee, even though I didn't understand what those words meant (see below for definitions). In my roles, I renew my commitment to them and honor their lives every single day. 

Here’s one thing I would say to my family if they could hear me. 

I miss you Carin, Mom, and Dad. 

Thank you for setting things up for me the best you could.  

XOXO - Michele

* Below are some definitions.  Yes, there's a bit of legalese, but I tried to use human terms, and we have added these documents available in the Caregiven App

  1. What is a Will?Caregiven Documents - Will
    • A legal document that details how to handle assets (financial and material) after death.
    • It names the executor/executrix (i.e., a personal representative) to give assets to beneficiaries, designate legal guardians for children, and provide clear instructions on how and when beneficiaries get inheritances.
    • IMPORTANT! You do not avoid the costs and delays of probate by simply having a Will -- What??? Read on, friend.

  2. What does the executor/executrix do?
    • They follow your will to the letter.
    • They administer the estate, resolve financial liabilities, settle taxes, and distribute assets.

  3. What is a Trust?Caregiven Documents - Trust
    • A legal entity with the sole purpose of protecting assets. 
    • A document with all of the planning details and benefits which are not part of a will.
    • This is the control document that clearly spells out who your assets are given to, but also how and when it will be paid out. 
      • Crucial point with children or people who can't handle money.
    • It has its own tax ID (i.e., social security number).
    • Names a third party, the trustee, to hold and direct assets in a trust fund.

  4. What does a Trustee do?
    • A trustee manages the instructions spelled out in a Trust.
    • Manages and handles other trusts if outlined in the original trust, like:
      • a Children's Trust
      • a Special Needs Trust
    • Prepares and files taxes, keep records.
    • Protects and manages trust asset investments.
    • Communicates with beneficiaries.

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