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Beware the Three Shoulds

It seems like you can’t swing a sourdough starter these days without hitting some unwelcome hot take on how we all should be spending our time during the pandemic. You probably remember the early comments about Isaac Newton discovering gravity and creating Calculus during quarantine, while ol’ Billy Shakespeare penned King Lear while waiting out the plague in 1606. I can forgive those takes, since we were young and foolish, and it was a different time all the way back in [checks notes] mid-March.

But even though those carefree early quarantine days are now behind us, the hits just keep on coming. We’ve been told we should emerge from quarantine with a new hobby, a new side business, a new fitness regimen, or a new appreciation for the joys of family togetherness.

The biggest thing wrong with these takes is not the suggestion that family togetherness is always a source of constant joy (although that’s a close second). These takes are wrong because they use one of the most destructive words in the English language:


This little word does a number on our minds and makes us squirm with discomfort (or worse) just because we have the unmitigated gall of being human and imperfect. It’s time to excise the shoulds from your life and vocabulary.

The Should World

Many of us approach the world as if it will comply to some unrealized ideal if we just believe hard enough.

For instance, I can remember reading some “undercover vegetable” recipes on a parenting website several years ago. These were recipes that folded zucchini or carrots or avocado or broccoli into kid-friendly foods like macaroni and cheese or meatloaf or brownies so that the presence of a nutrient-dense vegetable was imperceptible to a picky child. Such a deception ensured that said child did not succumb to scurvy and/or rickets while simultaneously avoiding a battle over the ingestion of said nutrient-dense vegetables.

As the parent of two picky eaters (who are starting to finally allow something other than beige foods on their plates), I am very much in favor of finding ways to ensure that children reach their full growth potential. However, some of the commentators on these recipes were clearly living in the Should World, because several of them opined thusly:

“Your children should eat their vegetables willingly and without having to be tricked into it!”

Careful scrutiny of this opinion will reveal a glaring issue within its internal logic. Specifically, it assumes that you can tell non-veggie eating children that they should eat their vegetables willingly and they will concede the point and immediately begin chowing down on asparagus while doing the dance of joy.

I’m not sure which children such commentators have known, but they certainly weren’t mine.

I recognize that these observers are trying to say that using a crutch like undercover vegetables won’t teach your kids to enjoy veggies for their own sake. But such editorializers don’t seem to notice that having a nightly battle with a child who is willing to make herself choke rather than allow a single molecule of cucumber to pass her lips also doesn’t engender affection for greens.

Living in the Should World can itself be a crutch, because once you have opined that something should be other than what it is, you can wash your hands of it, while still feeling like you have done something helpful. We’ve all seen the following singularly unhelpful comment within the personal finance world:

“Don’t know how you’re going to pay your bills after getting furloughed? Well, you should have saved 6-months’ worth of expenses in an emergency fund!”

Of course, this kind of comment is worse than useless, since it doesn’t help the individual with the problem and also shames them at the same time. And shame is the biggest issue with the world should.

The Three Shoulds

As far as I can tell, there are three ways that the Should World can shame you:

· Past Shoulds

· Present Shoulds

· Future Shoulds

Each of these should-beasts can trigger shame and make it harder to improve whatever situation you believe “should” be different. Let’s look at each one:

Past Shoulds

One of my favorite light reads is a 1980 Elizabeth Peters mystery called Summer of the Dragon. In the first chapter, anthropology graduate student D.J. Abbott realizes, belatedly, that she has done nothing to secure a grant for summer research when she hears all of her classmates talking about their upcoming plans.

When she approaches her advisor, Dr. Bancroft, for help, he tells her she should have thought about the problem back in November, rather than waiting until after all the grant proposal deadlines have passed. D.J., in a baller move, responds that it is not six months ago, it is now. She then hits her advisor with the following phraseone that I would like to have embroidered on a pillow:

“Let us deal with the situation as it exists, not as it might have been.”

(D.J. then accepts a job with an eccentric multi-millionaire to search for dragon bones in the Arizona desert. This is a job she would never have taken had she not forgotten to secure a grant for more legitimate anthropological research—but she gets a great adventure and a lovely romance and is part of one of the most important anthropological finds of the century. So, her procrastination and willingness to deal with the situation as it was were, all in all, a net gain).

I adore this book for many reasons, but I have to admit this tiny little moment in the beginning of the story has helped me to form my philosophy about the dangers of past shoulds. Dr. Bancroft, like many a financial expert, immediately starts in on what D.J. should have done.

It’s not clear what he (or any so-called expert who proffers such wisdom) expects such a person to do with those shoulda-coulda-woulda words of wisdom. Other than hang one’s head and mumble, “You’re right, of course,” there is absolutely nothing one can do with this kind of “advice.”

What makes past shoulds worse is when we internalize those past should statements and make ourselves feel bad about past choices, even if we don’t have a Dr. Bancroft available to helpfully point them out. (This is one of the reasons I absolutely love D.J. as a heroine—while Dr. Bancroft is yelling at her, she lets her mind wander to what she’s going to wear on Friday night for a date, because she’s got no time to feel bad about something she cannot change).

Things that you did in the past are not worth worrying about, since you cannot change them. Instead of letting yourself get hung up on the situation as it might have been, deal with the situation as it exists. You might find yourself on the adventure of a lifetime. Or find a solution that doesn’t involve beating yourself up.

Present Shoulds

Shoulding on yourself in the present is generally about feeling like you are falling short of some perceived ideal or goal. These kinds of statements usually begin with “I should be able to…”

Our present shoulds usually generate from within, rather than from the mouths of “helpful” experts. These are the stories we tell ourselves when we don’t live up to some sort of internal ideal.

I am a queen of present shoulding, telling myself I should be able to:

· Consistently write three articles every day

· Stay up past 9 pm

· Keep my house clean

· Homeschool my children during the pandemic without tears

· Wake up at 6 am

· Run for exercise (I’m more of a loper these days)

· Stop scrolling social media for hours a day

· Handle minor home repairs

During the quarantine, I have been feeling overwhelmed about my inability to effectively homeschool my kids. I have a degree in education, for heaven’s sake. I SHOULD be able to help my kindergartner learn to read and my 3rd grader learn math.

The thing is, this kind of should statement shames me for being exactly who I am. Yes, I may have a degree in education, but my degree is specifically in 6th-12th grade English education, and I avoided teaching 6th through 8th graders as much as possible. I adore my kids, but I knew all the way back in 2006 that I wasn’t cut out to teach little ones. Why would this situation be different?

Once I accepted that I’m not the ideal teacher for my kids, it became easier for me to figure out what I could do. The phrase that set me free was “so now what?”

“I should be able to homeschool my kids, but I can’t, so now what?”

Asking yourself “now what?” is like finally dropping an engine revving in neutral into a gear. Instead of spinning uselessly over and over about how I should be different, letting go of my “should be able to” and asking myself “now what?” allows me to move forward with a solution that doesn’t rest on me being different from who I am.

In the case of homeschooling, I’ve decided to focus on what we are good at—reading together, drawing together, making up jokes and games—while letting go of the need to be regimented with the schoolwork coming from the boys’ teachers. This isn’t a perfect solution, but it’s better than me feeling like a bad mom and a bad teacher and having us fight over schoolwork.

Future Shoulds

In some ways, these are the most pernicious of the shoulds, because they sound so reasonable. “I should save more for retirement,” you think to yourself. And this financial expert is here to agree with that statement. Yes, you probably should set aside more money for retirement.

The problem with future should statements is that they are too simple. “I should save more for retirement” sounds as simple and easy as “I should order some stamps online.” So you find yourself feeling bad about not crossing it off your list.

But most future shoulds represent a complex task that requires information, effort, resources, or time that you may not currently have. Your should statement doesn’t recognize the missing items, and so it just continues to sit on your mental to-do list as if it were a single, simple action you could take.

This is also where a lot of the quarantine hot takes seem to come from. “You should use your extra time to write that novel!” they suggest, as if writing a novel were a simple thing. This kind of suggestion assumes that all time away from your usual paid work is the same, ignoring that you need mental clarity (and a lack of existential dread) for creativity to flourish.

The best way to deal with future shoulds is to make sure you recognize their complexity. Don’t let “I should save more money” or “I should write that novel I’ve been thinking about” sit on your mental to-do list, looking for all the world like a single item that can be crossed off.

Write down what it is you want/plan to do, and then start clarifying what actionable steps you need to take. Break it down into its smallest component actionable steps, and put those steps in order. Then you can actually start getting to work on a small bite at a time, rather than continuing to beat yourself up for not “saving more money” or “writing a novel” or “curing cancer” or another big amorphous goal.

The Three Shoulds of the Apocalypse

The real world is a messy place. Things don’t go the way they should, and we are often stuck with the consequences of how things "should be" veering away from how they really are. Embracing the Should World can make us feel better, because we think that we will have a more just, manageable, neat, easy, and simple world if we believe in it hard enough.

But shoulding all over yourself and others is no way to bring about a fairer, neater, and easier world. The only way to make reality closer to the world as it should be is to accept things as they are and move forward from there, rather than wait around for what might be.

Note from Emily:

Things are chaotic right now. People are losing jobs or learning to work from home, kids are schooling online, and money is tight for a lot of families. 

I want to help. Book a free 15-minute call with me and we’ll create a plan for how you can weather this difficult time. I can guide you through getting your financials in order, creating a plan for your stimulus check or just help you prioritize your bills. 

Simple, easy, no catch, no push to hire me for more. I just want to help you be as financially secure as possible through all of this. Find a time and book your call here.

1 Comment

awe poor sad opossum! So agreed. And now "should" come with an dose of pandemic shaming, very publically, online. ugh! I hate this word, whether it's coming from someone else, or what I say to myself!

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