Don’t Should on Yourself

One of the things I’ve learned after sitting with hundreds of grieving families is that everyone seems to carry around a backpack full of “shoulds:”

I should have visited more.

I should have called one more time.

I should have noticed the signs sooner.

I should have been more patient.

I should have said, “I love you,” one more time.

Sometimes those voices come from inside us. Sometimes they come from well-meaning friends or family members.

“Shouldn’t you be feeling better by now?”

“Shouldn’t you be getting out more?”

“Shouldn’t you be moving on?”

One day in one of my grief support groups, we were talking about how guilt seems to be part of almost every grieving journey—and often for no good reason. One woman had spent nearly every waking hour caring for her husband during the last months of his life. Yet she couldn’t forgive herself for leaving him long enough to take a shower. Another person had called his mother every evening for years. Still, after she died, he couldn’t stop thinking, I should have called more often.

Then one member smiled and said, “Don’t should on yourself.” Not because grief is funny.  We all laughed because every one of us knew exactly what she meant. It’s a phrase I’ll never forget.

The more I’ve reflected on that conversation, the more I’ve realized that our “shoulds” don’t all come from the same place. 

Sometimes they come from hindsight. We judge yesterday’s decisions using today’s knowledge.

 “If only I’d known then what I know now…”

But often it’s something even deeper. Death confronts us with one of the hardest truths in life: there are some things we simply cannot
control. We’d rather believe we made a mistake than accept that some endings cannot be prevented. Our brains don’t like that, so they begin searching:

Maybe I missed something.

Maybe I made the wrong decision.

Maybe if I’d done one thing differently, the ending would have changed.

As weird as it sounds, guilt can feel easier to carry than helplessness. If it’s my fault, then maybe I had control. And if I had control, maybe I could have changed the ending. Maybe that's where so many of our "shoulds" come from—not because we loved too little, but because we wish we had the power to rewrite the ending.

But grief keeps teaching us something much harder to accept: love is powerful, but it isn’t all-powerful. We cannot control every illness, every accident, or every goodbye. Sometimes our minds invent “shoulds” because they feel safer than admitting we couldn’t stop what happened.

And sometimes our “shoulds” come from love itself. Love has a way of searching for unfinished business:

Did they know how much I loved them?

Did I spend enough time with them?

Did I say everything I needed to say?

Those questions don’t necessarily mean you failed. More often, they’re evidence that you loved deeply.

Your relationship wasn’t defined by one phone call. 

Or one missed visit.

Or one difficult conversation.

It was built over hundreds—even thousands—of ordinary moments of loving, laughing, forgiving, serving, and simply showing up.

So when the “shoulds” begin piling up this week, pause for a moment and ask yourself a different question:

What would my loved one say to me right now?

My guess is they probably wouldn’t begin with the word should.

Remember

Don't should on yourself.

One Step Forward

This week, notice every time you catch yourself saying, “I should have…” Before you finish the sentence, pause and ask yourself:

Am I speaking from love…or from guilt?

Remember that guilt asks you to replay a past you cannot change. Love invites you to remember the relationship as a whole—not just one moment you wish had been different.

Consider This

If your loved one could speak to you today, would they ask you to carry this guilt—or would they invite you to let it go?

Until next week, remember: don’t should on yourself. Love remembers more than guilt does.

Peace,
Tom