Shake Off Your Shoulds

Oct 14, 2022

Shake Off Your Shoulds

How often do you come to the conclusion that you should be doing something else?

If you’ve heard the last few weeks of the Go First series by Pastor Jared, you’ve probably heard him say something about letting go of the “shoulds.”

I love his reminders because “shoulding” is something I giggle about all the time. It’s something I’ve grown hyperaware of over the last several years, especially as my children have continued to grow from newborns to toddlers to… well, kids.

As someone living in our culture in 2022, every day, you attempt some sort of new balancing act.

You may be balancing multiple jobs (I mean, gas in San Diego is like $7 a gallon - hello!). Maybe you find yourself balancing a growing career with an active personal life. Or, maybe you’re balancing a health challenge on top of just daily living.

If you’re anything like me, that need to balance causes you to feel behind as you check your multiple to-do lists constantly throughout the day, both at home and at work, saying, “I have to do this, this, this, and this - buuuuuut I should be doing that… or that… and definitely that.”

We "should" all over ourselves without even thinking about it.

How many times a day are you thinking something like:

  • I should have made my child’s costume.
  • I should be able to buy a house by now.
  • I should eat more dark leafy greens.
  • I should go workout.
  • I should visit or call that family member.
  • I should be less insecure.
  • I should give back somehow and volunteer more.

Whatever is on your “should” list, I know you’re balancing something and having to actively choose what you’re doing while wrestling with the other 10 things in any given moment you feel you should be doing.  

But friends! I’m here with a special reminder and permission today:
Please, stop should-ing yourself to death. (Hahaha, yes, you can laugh with me here.)

As apprentices of Jesus, we’re called to the opposite of “the shoulds.” Because when we “should” all over the place, you know the result: guilt.

And what is guilt? Ultimately, it's a nasty recipe of a little bit of fear, sprinkle in some doubt, and, of course, a whole cup of anxiety. All rolled up into an unwelcome, yet all-too-familiar, mix which can derail the best of us. And lead us straight away from Jesus.

But, what is an alternative mindset we can take when we find ourselves “shoulding” all over the place?

In Matthew 11, we read that Jesus has just finished teaching his 12 disciples. While it doesn’t say exactly what they were working on, it does then say in verse 1,

... he went on from there to teach and preach in their towns.
- Matthew 11:1

I like to imagine that he gave his disciples a sneak peek of his lessons and then began sharing them more widely.

Then it says,

When John, who was in prison, heard about the deeds of the Messiah, he sent his disciples to ask him, “Are you the one who is to come, or should we expect someone else?”
- Matthew 11:2-3

Did you catch that???

John the Baptist throws out a little doubt with that should, doesn’t he?! Maybe even a little exasperation, like, “Ok, we’ve seen a lot of stuff going down here so is this it, or should we keep waiting for something else?”

To me, John sounds a lot like when I’m tired, maybe a little impatient, and I say something like:

“Did you do prep dinner, or should I plan to handle that when I get home?”
“Were you able to get your homework done, or should we do that later tonight?”
“Did you put the cover on the TPS report, or should I take care of that, too?”

Any of that sound familiar?

While all shoulds are not created equal and carry different meanings, I do love how Jesus went on to provide an alternative path for our thinking.

Here’s what He says when it comes to the shoulds (our guilt, doubt, impatience, anxiety, exhaustion…):

“Are you tired? Worn out? Burned out on religion? Come to me. Get away with me and you’ll recover your life. I’ll show you how to take a real rest. Walk with me and work with me - watch how I do it. Learn the unforced rhythms of grace. I won’t lay anything heavy or ill-fitting on you. Keep company with me and you’ll learn to live freely and lightly.”
- Matthew 11:28-30 (MSG)

Just for today my friends, don’t let your “shoulds” have the run of your thinking. Instead of giving the typical doubt and anxiety the reins of your life today, try leaning into Jesus’ above offer in Matthew 11:28-30.

And when you hear yourself inevitably begin to should, here’s a list of practical shifts you can make while you meditate on Jesus’ words.

Instead of “should,” replace it with:

  • I want to ...
  • I would like to ...
  • I hope ...
  • I pray ...
  • I will …

And then take it one step at a time from there.  

Love you!


Kyle Moss

I read this devotional
Shake Off Your Shoulds