By definition, every single client we work with is thinking about their death. They’re planning for the day they’re no longer here–and making sure their loved ones and favorite charities are cared for. That’s incredibly impactful work. It’s not always easy, but it can eliminate tension in a family and significantly decrease the taxes paid by an estate or its heirs. Last month we talked to grief therapist Grief Therapist Brittany Squillace, MA, LMFT about anticipatory grief: the emotions that can come with thinking about someone’s legacy–or realizing that a parent or loved one won’t be here someday. We recently sat down with Brittany to talk about grief as it coincides with legacy planning. Here’s what she had to say: 

How do you describe grief? 

The whole mission behind my YouTube channel is to “expose grief.” It’s so important to expose it for what it is: simply a natural and healthy way of living and loving. We are expected to only grieve the loss of a loved one for a short amount of time, when we’ve loved that person for years, decades, or a lifetime! We wouldn’t mute our love for someone when they’re alive…so why would we when they’re gone? Everyone has the right to process and honor their grief in whatever way they need. Grief is normal. It takes time. And it looks different for everyone. 

What does grief look like, or what are some ways that grief typically manifests in people’s decision-making and ability to function?

Almost without fail, in someone’s first or second grief therapy session, a client will ask if something is wrong with them. “Don’t I sound crazy?” they’ll ask. I hear this so often that I made an entire blog post about this phenomenon. When I hear a client say those words, I think, “No, but go ahead and tell me why.” 

Often what I’ll hear is that people have a lack of identity after someone is gone. They say they don’t know what their life looks like without that person, or “I don’t know who I am anymore.” They feel a lack of purpose or motivation, especially if someone was a caregiver. 

On the flip side, and especially for caretakers, they may feel relief, and then guilt around being relieved. 

For some, anger might be grief. Some people hold a lot of anger toward the way in which a loss happened. Or they might have unresolved stuff–conflict–with the person who passed, which makes grief more complex. Or they might have anger toward how other people are grieving, simply because their process looks different. 

Some people also want to gravitate toward tangible things that belonged to a person. That’s a very common dynamic, so I help clients through those tangible tasks like going through the deceased person’s belongings. It’s a process that’s frequently used in our industry, and something I call creating “Piles of Love.”

I also help people think about how to set boundaries around their relationships with others while they’re in the grieving process. Some run into friends who begin to only see them as a grieving individual. Friends see them as always sad, or “not the same as they used to be”–so they don’t invite them to things or assume they’re not ready to move on. That isolation, and those unfair expectations, can compound feelings of grief. So, it’s important to articulate–to friends and family and support networks–when the grieving person is ready to begin re-entering regular commitments, engagements, and tasks. It might not look the same–right away, or ever–and that’s ok! 

What are some tips/tricks for dealing with grief, if someone notices themselves becoming incapacitated by it?

In our last discussion, we covered some tips for knowing when to seek therapy–and what to look for in a grief therapist. 

But not everyone is ready for therapy, and there are ways to ease into this work without fully committing or spending a ton of time or money. It can be a little less overwhelming to explore from home, so here are a few grief-related resources and support groups I often recommend:

I also love anything and everything by Alan Wolfelt. He’s created tangible workbooks to help people start processing their grief. 

Do you have any ideas for how someone might plan for grief in their legacy plan? 

First of all, I’d love to normalize setting aside resources to support family members who are grieving. I love that Apex helps clients think through what can be done–financially–to make sure surviving loved ones are supported after someone dies. Just like people give financial gifts to their children/heirs in an estate plan, set aside funds for therapy or even a vacation for the family to process the loss together. 

And then label it. Don’t expect grief to show up in a debilitating way in the legacy-planning–or estate settlement–process, but don’t be surprised if it does. Being blindsided by grief is the most frustrating. Sometimes you might have to remove yourself from a conversation surrounding your plan or someone else’s, because these things can–and should–get emotional at times. Set some boundaries if a conversation is becoming difficult. People know their family dynamics; one person might not be emotionally able to be as involved in discussions, but it’s important to still bring them up to speed. 

What about estate provisions someone can make for key moments they might miss down the road? 

This is so different for every family–and every person within a family. It’s important to talk about this. Ask an older family member how they want to be remembered. Ask, “How do you want your memory to be kept alive in our family?” Or if you’re talking to your children and grandchildren, think about how you’d like to be celebrated after you’re no longer here. At our wedding, my husband and I put photos of our grandparents, who are no longer with us, on empty seats in the front row. It was a beautiful way to remember them and hold space for them–and my family’s grief–during that special day. 

If you have ideas like that, tell your loved one, “Hey, we thought about doing A, B, or C to remember you. Would that be ok with you? Is there a different way you’d like us to incorporate you into our marriage, or a child’s graduation, after you’re gone?”

The important thing is to honor their wishes–and to create moments that fit your family and the relationships you have. 


Brittany Squillace, LMFT

Brittany Squillace, LMFT

Grief Counselor, Best Self Therapy

When Brittany lost her grandparents, she witnessed firsthand the effects of grief on her family. That experience–and workforce shifts brought on by COVID-19–led her to begin her own practice, Best Self Therapy, based in Eden Prairie and offering virtual appointments to clients across Minnesota. Squillace is passionate about offering people a safe place to process their grief and supporting caregivers to those facing the end of life.

Brittany has a Master of Arts in Marriage & Family Therapy from Saint Mary’s University, is a Licensed Marriage & Family Therapist (LMFT), and a member of the Association for Death Education and Counseling (ADEC) and the Minnesota Coalition for Death Education and Support (MCDES). When she’s not supporting clients in transitional stages of their lives, she does personal training, travels with her husband, and loves hanging out with their two mini golden retrievers, Vega and Lyra. 


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