“The Shoulds” by Lori R. Keeton

“What are you going to do when you get home?”

I look over at the pile of work that has sat untouched for the entire weekend and say “I should work.”

Then, I sigh.

A deep, heavy, burdened sigh.

This brief exchange took place between my mother and me a few weekends ago as we were leaving to go our separate ways after spending the weekend together in Virginia.

It stayed with me the whole way home.

The “should” I mean.


(Deep, heavy, burdened sigh.)


I truly hate that word.

I hate everything it stands for and everything it makes me feel.

If I could eradicate one word from my vocabulary that would have the largest positive effect on my life, it would be “should” (Well, it would actually be “yes” in response to all questions that involve alcohol, dessert and/or inappropriate men, but that’s another blog).


I should eat healthier.

I should exercise more.

I should work more.




I recently observed an elementary school English class where the kids were excitedly singing “Conjunction Junction, what’s your function? Hooking up words and phrases and clauses…..”


Remember that song and how it taught you to listen for certain words to know what words would be coming next?

I got to thinking about what “should” signals is coming next.

Poor “should.”

There is just nothing good that follows it.

“I should….”

” I should have…”

“Should I….”

“You should/should have….”
JUDGMENT (and a nice dash of your own insecurity for having to act as though you have it all figured out).

Even if you try and dress up its ugliness by pairing it with something “good,” it still does not lead to a feeling of joy or gratitude or excitement….


“I should take a vacation” or “I should eat more dessert.” (Side Note: If you are a Size 2 and say this while bemoaning your inability to gain weight, we will never be friends. Ever. You have been warned.)

That’s the toxic power of “should”- it can take amazing, wonderful things- like dessert and vacation- and make them negative.



The word can literally swallow up entire years of our lives- entire relationships, entire careers, entire chapters.

And God it’s heavy.

I can look around my office or my bedroom and literally spot the “shoulds” everywhere I look like a “Where’s Waldo?” puzzle of guilt….


Piles of bills
“Things to Do” lists with nothing crossed through
Self-help books with unbroken spines
Dirty laundry

And so it goes.

The only thing more toxic than the “shoulds” is the “should haves.”

“I should have left my job/marriage/______________ (fill in the blank with whatever regret is eating you up at the moment) sooner.”

“I should have said no/yes/maybe.”

If God ever decides to let us live our lives backwards, I am sure all of these “should haves” will prove very useful.


Otherwise, what a colossal waste of time.

And the strange thing is that as powerful and destructive as “should” can be to our lives and our happiness, it is equally wishy-washy and weak.

Let’s face it- it isn’t like “should” inspires immediate action. It doesn’t. It inspires dread and delay.

Think about the Bible. God doesn’t tell us we “should” and “should not.” Nope. As a friend once told me, they are commandments- not suggestions.


“Thou shall/shalt not…” sounds a lot stronger and scarier than “Thou should not…” (And it makes things pretty air tight whether we like it or not.)

I have yet to hear one of my friends calmly say “You should not do that” when their kids are pummeling their siblings or spilling paint all over the carpet.



Recommendations, best practices, guidelines, suggestions. As a lawyer, when I read those words, what I really see is “Not required. Not binding.” No matter what you call them, they are all just a bunch of “shoulds.”



So what do we do with these maddening strong/weak “shoulds”?

Well, you should… Scratch that. Let me try again.

I do not know what you should do with your “shoulds.” As for me, I am trying to really listen to my “shoulds” and look for patterns. Are they coming up often with regards to my job? My friends? My family? Do they seem to relate to the same types of things over and over? Are they someone else’s “wants” that become my “shoulds”?

And maybe the most important question of all: How can I reduce the “shoulds” in my life and increase the “wants”? How can I create a calendar- a life- that is filled with things I want to do rather than that I feel obligated to do?


I think for all of us there is this struggle between who we think we should be versus who we are. And maybe that contrast is best understood by looking at our “shoulds.”

There are some people who are completely oblivious to this struggle. They have more or less looked around at our society and made a list of the things they are “supposed to” be and they refuse to look beyond that. They just set their minds to being it.

“I should have a good job…. I should have a spouse… I should have kids…. I should make lots of money…. I should belong to this club…. I should drive this car…. I should live in this neighborhood…. I should wear these clothes….”

And all these “shoulds” culminate into perhaps the worst “should” of all- “I should be happy.” But they aren’t.


Others- and I put myself in this category- struggle with the question- knowing that where they are isn’t where they are meant to stay but also being uncertain of where their “there” is located. There are times it feels like you are putting together a jigsaw puzzle, taking all kinds of experiences and jobs and relationships and more or less trying to see if they fit into your puzzle.


While I don’t know the secret to putting my (or anyone else’s) puzzle together, I do know that the “shoulds” are perhaps the worst road map of all.

Don’t get me wrong- the “shoulds” are tempting.

The path is so well-lit and easy to find. There are no hills, no sharp curves, no bumps. And it looks so damn perfect on the outside. Pristine yards, shiny windows and white picket fences (or maybe electric fences in this day and age).


And part of the reason it is all so tempting is us. We want to believe them. I want to believe them. It is the same reason I find myself ordering diet pills at 3 a.m. after watching a cheesy infomercial that promised I could eat whatever I wanted and still lose weight if I just took some pill. Give me that pill. Give me that life. I want it to be true.


And the people pedaling their “Christmas card worthy” lives are also great salespeople.


But the problem is, they are lying. Some may know they are being dishonest. But for most, I don’t think they realize it. I think they have lied to themselves for so long and worked so frantically to try and fill up their emptiness and insecurities that they don’t even know the truth anymore. They just can’t let themselves see it.

It’s tragic really. A beautifully wrapped package of air.


From what I can tell, the road to happiness is rarely Christmas card- or even Facebook status- worthy.


The road is bumpy and curvy and dark.

There are lots of detours.


And it always seems to be under construction.


There aren’t nearly enough “rest stops” for my taste.

You have to sit still at times and wonder if you will ever get to your destination (and try not to curse incessantly in these still times).


And sometimes you break down and literally have to wait for someone to come and help you get going again.


And the truth is we probably could be spared a lot of the pain and heartache we will encounter on this road if we followed some of those damn “shoulds.”

But by God, at least it’s YOUR road.

It may not always be pretty, but it is real.

And there are some amazing parts to it–

Sitting outside on a warm summer day with your friends telling secrets.

Laughing with your parents.

Kissing someone for the first time (or like it’s the first time).


Staying in your pajamas all day.

Soaking in a bubble bath with a big glass of wine and a trashy magazine.


Getting flowers unexpectedly.


Being told your beautiful/smart/courageous/amazing/all of the above

Finding the courage to try something new.

Holding a new baby.


Walking on the beach.


Forgiving someone.

Meeting someone who makes your heart race.

Experiencing the kindness of strangers.

So I guess maybe there is a point to all the “shoulds” that seem so relentless at times.

Maybe they are in fact the lights, the guideposts on our roads to happiness.


Maybe we encounter them to alert us when we are drifting off our road onto someone else’s, to tell us that the puzzle piece we are trying to make fit just isn’t the right one for us.

So maybe there is something good that can follow “should”– so long as it isn’t us.