When You’re Feeling Guilty All the Time

The Should Monster

To those feeling guilty about everything,

I didn’t used to believe in monsters.

I’ve long grown out of the days where I check my closet for claws or jaws. I can boldly go down to the basement alone at night without fear of the furnace devouring me. Occasionally, I make a long leap for the bed, forbidding the monster to grab my legs.

No, this monster is different. This monster doesn’t live under a bed or in a closet. It goes with me everywhere.

To the store.
To my job.
In my home.
At the bank.
To the mall.
Out to eat.

His name is the Should Monster.

What the Should Monster Looks Like

One of the superpowers of my Should Monster is transfiguration. He can look like many different dreadful creatures. When he follows me to work, sometimes he takes the form of my email inbox. As I dismiss my last child after a hectic day of teaching, I creep to my inbox and catch up on missed emails. That’s when the should monster exposes his teeth.

You should have completed three weeks of lessons by now.

You shouldn’t have taken that 15-minute lunch break to scroll on your phone. You should have gotten a few things checked off the to-do list.

Did you really teach that lesson this way? You should have done it the other way.

By now, the Should Monster has left me in a panic. The words on my screen begin jumbling together, and I can’t process anything. All I see is the monster staring back at me until I slam my laptop in fear. I grab my keys and scurry out the door, leaving my desk flooded with used sticky notes and ungraded papers, only to return the next day to see the Should Monster’s grimace when I crack open the laptop once again.

The Should Monster’s scare tactic is guilt.

What the Should Monster Sounds Like

When the Should Monster follows me to the store, he starts talking his way through every aisle. His words drip with contradiction and shame.

You really should have a nicer kitchen. You should get some things to update.

So I throw some items in my cart, trying to get the Should Monster off my back. But by the time I pace through the check-out line and get up to the register, he strikes again…

You really shouldn’t be spending your money on things you don’t need.

So I set it all down. I leave the store empty-handed, my body captive to the guilt this monster throws on me everywhere I go.

My own home is not even sacred. There, he nags about where I should be in life, how much I should be making, how many friends I should have, the wife I should be, what I should have said…

The Should Monster’s weapon is comparison.

Battling the Monster

The truth is, you could be at the top of your game or losing by fifty in the fourth quarter. The Should Monster is relentless. This is why rather than avoiding him, we must battle him in practical ways.

Create a Done List

When the Should Monster tells you that you aren’t doing enough, you don’t need another fancy to-do list or innovative time-blocking schedule. You need a done list.

My mom shared the done list with me the other day, and I think it’s genius. Think of the things you HAVE completed today. You can write them down or make a mental check-list. Give yourself grace and praise for what you did do today, even if the most productive thing was simply showing up. You’re doing okay, friend.

Paddle Your Own Boat

If my productivity and mental stability is like heading down a stream, the oars that push me forward are things like positivity, encouragement, and grace. The Should Monster is the person in my boat who is desperately paddling the other direction.

Guilt tactics and comparison techniques never propel me forward. They only make me want to jump out of the boat altogether. If there is a certain person in your life that mimics the Should Monster and uses scare tactics to steer you, it’s time to put them in check. You cannot let them paddle your boat.

Set up boundaries. Create a phrase to repeat to yourself when the battle starts. Have a conversation. Whatever you do, don’t let their tactics prevent you from throwing the oars down altogether. Paddle your own way.

Look at Yourself from the Outside

It’s not about if the Should Monster will show up or not – we already know he will. It’s about if we allow him to affect us when he makes his appearance. Oftentimes, we allow harsh and cruel things to be put on us because we feel like we deserve them. We think they will keep us humble.

Put yourself on the outside. Would you think another person wasn’t doing enough given their life circumstances? Typically, when I look at myself from the outside perspective, it reminds me how outrageous some of the Should Monster’s lies really are.

Remember How Good You’re Doing

The saddest thing about the Should Monster is that he finds some of the strongest, most talented, and courageous people to attack. The best people find themselves trying to leave their careers. The most passionate are seeking new passions. The strongest are wanting to quit.

I want you to know how good you’re really doing.
I want you to know you’re not a number.
You’re not what you achieve.
You’re not what people think.
You are loved. Special. Valued. Enough. And there is no Monster big enough to steal the important role you have in this world. Don’t abandon your boat. Keep your oars. Paddle on, friend. I’m paddling beside you.

Today is Sunday. The Should Monster makes his rounds to the Brown household every Sunday afternoon, using guilt and shame to thrust me into the week ahead.

But that’s not what I choose to meditate on today. Today, I choose to knock him out of my boat. I choose to call a friend. I choose to hug my cat. I choose to use my finest china for tea even though I’m in my pajamas.

I choose to believe that I’m enough. And I’m called. And I’m doing okay.

And so are you.

Sincerely paddling,


One thought on “When You’re Feeling Guilty All the Time

  1. Becca, such a good reminder that we can only do the best we can, let go of things we cannot control, and trust God with it all. It’s not easy to hold onto our peace in this crazy world pulling us in all directions!

    Liked by 1 person

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