“But should you, really?” or, How to Challenge Your “Shoulds” and Get Back to What Matters

How many shoulds or supposed-tos do you utter in a day? How often do you put yourself down because you’re not doing something you believe you should be doing? And how many times do you think critically about whether taking those actions would actually benefit you? And if they would benefit you, whether you have the resources to do them well?

My inbox is a horror show of shoulds and supposed-tos.

There are the podcast guest pitches that invite me to interview the 23-year-old who is making 7-figures per year selling cheaply produced goods at an incredible markup on Amazon (and why you should, too). There are emails from marketers who promise me more money if only I would do X, Y, OR Z. And then, there are the HARO emails.

I get emails from HARO (Help a Reporter Out) three times a day. Each email contains queries from journalists—some looking for experts, others looking for first-hand experiences. Here are some selections from this afternoon’s email:

• “Here’s everything you need to know about scripting manifestation”
• “Winterizing roses: tips on what to do”
• “How to prevent carpal tunnel if you type for a living”
• “How to create a smart laundry room”
• “These equipment-free exercises will give you the same fitness benefits as running”

A while back, a publication was looking for all the shoulds and supposed-tos of preventing snakes in your house and getting snakes out of your house. I don’t want snakes in my house—but I also don’t think I need to worry too much about snake-proofing. At least, I hope not.

Anyhow, there’s a lot you can learn about the state of service journalism from HARO emails.

Service journalism is how many online publications drive traffic today. And it offers some great examples for noticing and challenging our shoulds and supposed-tos. Writers of service journalism produce articles that serve the reader by connecting them with recommendations and expert advice. These articles often have clickbait-y titles and search engine optimization formatting. Some service journalism is really valuable. And some is trash.

Each of the queries that I listed above (which are just titles) is a service journalism assignment. Let’s say I’m a rose gardener—I’m not—and I know I need to do some things to make sure my roses make it through the winter. But I can’t remember what all I’m supposed to do! So I search “how to winterize roses.” Ideally, I’ll see “Winterizing Roses: Tips On What To Do” pop up in my search results. This is great. I love that I can find answers to straightforward problems so quickly.

However, service journalism pieces are often used to create a need where there wasn’t one before.

For instance, maybe I’ve never considered having a “smart laundry room.” I’m certainly not going around searching for smart washing machines. But then I’m checking the headlines at CNN and notice a post about smart laundry rooms. This hypothetical article is in their “Underscored” section—which is where CNN posts product reviews and round-ups to drive affiliate revenue. The article explains why a smart laundry room would be a great addition to any house and how to set one up. In the process, it also recommends a variety of appliances and networking devices. Suddenly, I’m thinking I really should have a smart laundry room—and maybe some other smart appliances, too.

Not every should or supposed-to is shaped as such a blatant marketing ploy. In the same way that articles listing the best morning routines for Millennial executives or touting the benefits of the latest superfood, our beliefs shape our shoulds and supposed-tos as well.

Decoding Explicit Shoulds & Implicit Shoulds

Shoulds are often stated explicitly. For instance, one might begrudgingly admit, “I really should be spending more time on LinkedIn to find new clients.” Or, your mother might not-so-subtly hint that you really should call more often. Explicit shoulds are easier to notice and vet—e.g., Should you really spend more time on LinkedIn? Or are there more effective ways to connect with new clients?

But many shoulds are implicit. An implicit should is the story behind the story. Let’s look at another of the HARO queries as an example: “These equipment-free exercises will give you the same fitness benefits as running.” The word should doesn’t appear anywhere in this query—but it’s dripping with shoulds and supposed-tos under the surface. First, this headline takes for granted that one really should be exercising. Valid or not, it’s a should. Second, it implies that one should be running, but there are other ways to get the same benefits. Third, the headline hints that one should stop making excuses because there’s no need to buy expensive equipment. 

I realize this is some very close reading of a headline for a yet-to-be-written article. And it’s a relatively anodyne fitness-related headline at that. But this is exactly my point: shoulds and supposed-tos are everywhere. And we often take them for granted because we tell stories, consume headlines, and engage marketing that imply those shoulds. Without a closer reading, we won’t notice when we take a belief for granted and allow ourselves to challenge it. 

Assuming that noticing your shoulds and challenging them is something we’re interested in doing (because I’d hate to give you yet another should), how exactly do we do that?

Step One: Notice 

To challenge a should, we have to recognize the should first. In the case of explicit shoulds, that’s fairly easy. We can develop quite a reflex around the word—whether we’re encountering it in the wild or voicing it in our own brains. 

But for implicit shoulds, we need to be a bit more crafty. I practice noticing shoulds in low-stakes situations. So if I’m scrolling through Twitter or Linkedin and I see a post that’s getting a lot of play, I know there’s a good chance there is at least one should embedded in that post. I stop my scroll and see how many I can find. The more I practiced like this, the easier it became to spot shoulds on the fly.

It might take some time to master noticing the shoulds. It’s worth giving ourselves the grace to spend enough time just paying closer attention to how they show up.

Step Two: Contextualize

Once we’ve spotted a should, then we can give it context. What beliefs does this should take for granted? Who is it actually aimed at? Is there evidence to support its claim?

Let’s go back to the example: “I should spend more time on LinkedIn so I can find new clients.” The beliefs this should takes for granted are that my clients are active on LinkedIn and that the content I post attracts those people to my services. It also takes for granted that the people I want to meet on LinkedIn are even looking to contract a service like mine. Those things might all be true—but acknowledging them is key to making an informed decision about whether this is something I actually want to pursue. 

This particular example of a should is one I’ve given myself, right? But it came from somewhere. Maybe I’ve heard a bunch of people talking about how they’ve gotten clients from LinkedIn. Or I’ve read a few articles touting the results they’ve gotten from their LinkedIn use. That sounds good—but do those people operate the same kind of business I do? How do their social media habits compare to mine? Do my clients and their clients have anything in common? It’s entirely possible that LinkedIn is a great place to spend time for a set of business owners and freelancers—but that set of people might have nothing in common with me or my priorities.

And a final note here about evidence: an anecdote isn’t evidence.

It’s one data point. Splashy anecdotes often communicate all manner of shoulds.

For example, in January, I learned about LinkedIn newsletters from a post on Medium that explained how one guy got a thousand newsletter signups in five hours by starting a LinkedIn newsletter. You know what I did? Yep, I started a LinkedIn newsletter the next week. And while my results were pretty great, and I’m glad I did this experiment, I certainly didn’t receive a thousand signups in a matter of hours. I recognized that anecdote wasn’t a promised result—but it was intriguing, aligned with my priorities, and seemed to apply to people like me. I decided to try it not because I should but because I was making an informed decision based on an intriguing anecdote. I knew his results wouldn’t be my results, but I wanted to gather my own evidence.

Step Three: Assess

In the above example, I made a quick decision about a potential audience-building tactic because I knew what my strategic priorities for the year were. I wanted to connect with and engage as many potential book readers as possible. And I wanted to continue my focus on remarkable content—while playing with new modes of distribution and rhythm. 

I use my strategic priorities as a key assessment tool to decide whether an intriguing idea is just that—an intriguing idea—or an idea with trying. Strategic priorities aren’t goals, and they’re not projects. Strategic priorities are directional guidance—like a highway sign (I share more about strategic priorities in my book, What Works). A sign that has nothing to do with the direction I’m going or the destination where I’m hoping to end up is easily ignored. But a sign that references my direction or destination draws my attention. 

Some shoulds may help us get where we’re going. And those are important to pay attention to. But other shoulds are just random highway signs that tell us nothing about where we’re going or how to get there. Yet, they are the same size, shape, and color as the signs we do want to pay attention to.

Personal values, personality traits, strengths, work styles, etc.—these can also be used as ways to assess whether a should is really a do or not.

The Principle of ‘Ought Implies Can’

When I spoke with Charlie Gilkey about cracking the code of shoulds and supposed-tos, he introduced me to Immanuel Kant’s principle of ‘ought implies can.’ The idea is fairly straightforward (at least as Kantian ideas go). ‘Ought implies can’ means that a should is only a moral obligation if one can do it. If one can’t take a particular action, then there is no moral obligation to do so. In other words, if we don’t take action we can’t take, even if it would be moral to do so, we haven’t done anything wrong.

I know the word “moral” can be tricky for many people. But essentially, we can think of “moral,” in this case, as the difference between good and bad, right and wrong—and set aside any religious notions of morality.

Charlie told, “We might talk about [this principle] in a moral philosophy class, but when we talk about on a day to day living, so much of our suffering comes from those two things: We apply a should or an ought where we can’t, and we apply an ought or a should because it might be good to do.”

Our positive thinking, hustle culture, and rugged individualist beliefs convince us that there are far more things we could be doing that we aren’t.

And so we feel bad about ourselves. We might even label ourselves lazy, a slacker, or just “not a go-getter.” But we’re giving ourselves grief for actions we might not have the resources to do, let alone do well. I’m not obligated to do something I can’t do, even if doing so would be good for my career.

If I didn’t have the time, mental bandwidth, or knowledge to produce another piece of content on LinkedIn each week, I couldn’t obligate myself to do it—no matter how much it aligns with my strategic priorities or other factors. There is no reason to put myself down just because I’m not doing something I can’t do, given the current circumstances. 

Of course, we do exactly that all the time.

“But why?”

Whenever I’m talking to someone who is getting down on themselves over a should, I respond with one of my favorite questions of all time: “But why?”

Why should you do that thing you’re not doing? Why would it be good for you? Is that good actually something you even want? Have you considered what resources taking that action would require? Do you have those resources to give?

So often, the only thing we need to stop a should or a supposed-to in its tracks is a moment of clarity—a brief pause in our go, go, go reaction.

That’s the only should I’ll leave you with. The next time you’re hung up on a should, take a beat and see what happens. I know you can do it.