511. Should 😱

How and why I'm learning to recognize the "shoulds" in my life

Hellooo 👋 So happy to have you here. I’m Kevan. I have spent 15+ years as a head of marketing for some cool tech startups. Now I’ve co-founded a brand storytelling business called Bonfire. We do coaching, advisory, and content. If you identify with creativity and marketing, we’d love for you to join us.

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I should really stop saying “should”

Photo by Javier Allegue Barros on Unsplash

The 10 most common “shoulds” from a career in marketing …

Any of these sound familiar?

1. I should post more on LinkedIn

2. I should climb the corporate ladder: be a manager, be a CMO

3. I should network. I should want to network

4. I should be growing my business / pipeline / revenue at least 2x per year, if not more, every year, always and forever, amen

5. I should know what EBITDA stands for [or whatever term I’m unsure of]

6. I should be a [fill in a job title] by now

7. I should be more assertive among leadership

8. I should know what to do next, without having to ask anyone

9. I should never admit I don’t know something

10. I should spend more time in the numbers or in the strategy or in the weeds (wherever I’m not spending time now)

The problem with “should”

I’ve had imposter syndrome on the mind lately.

(Honestly, it’s never far from mind.)

My Bonfire co-founder

Shannon Deep

wrote a wonderful essay about imposter syndrome last month, and it has led to some really great conversations since. We’ve talked to friends, to peers; I even hopped on Andrew Capland’s podcast to talk through the worst moments in my career 😳 (the episode comes out soon; I’ll let you know.)

Here’s the imposter syndrome essay, if you’ve yet to read it:

20. The Cure for Imposter Syndrome

Imposter syndrome, as many of us are familiar, comes from a perception that we aren’t enough, that we’re not doing enough, that we aren’t successful enough, that we’re going to be found out. It is marked by “feelings of self-doubt, anxiety, depression, and/or apprehension of being exposed as a fraud in [our] work.”

This often leads me into try-hard territory where I look at what the non-imposters are doing and tell myself I need to do those things — that I should do those things.

“Should” assumes some unspoken expectation. It presumes that there is one way that things work, that there is a recipe that we all must follow. Or else!

Of course, “shoulds” can sometimes be useful. Like most things, it is a spectrum. When I knew nothing about how digital marketing worked — roughly my first five years in tech — I was happy to have people guide me toward the “shoulds” of my new role. But as time wore on, I found that there is a line between taking inspiration from others and chasing a constantly-moving target of what I think others expect from me.

Dr. Kristin Neff, a psychology professor at the University of Texas at Austin puts it this way:

Though the “shoulds” can spur you into action temporarily, over-“shoulding” can carry negative side effects, like reinforcing fears of being unacceptable and a fear of failure. “This actually creates performance anxiety and [feelings of] failure, which undermines your ability to achieve in the long run.”

Another helpful lens on “shoulding” comes from Dolly Chugh’s book The Person You Mean to Be. Dolly describes a phenomenon called “identity granting.” Basically, it’s one thing for me to identify as a really good marketer, but until someone else thinks I’m a really good marketer — until that identity is granted to me — I’ll always be chasing that validation, which typically leads me back to all those “shoulds.”

Each of us has an intense craving for others to see and acknowledge our various identities, a phenomenon that Bartel and Dutton call “identity granting.” They compare the interplay between identity claiming and granting to a public performance and audience reaction. Tina Fey may claim an identity as a funny person, but if audiences don’t find her funny, her identity as a funny person has not been granted. We are vigilant for clues about whether our identity has been granted. 

Psychologist William Swann has studied how much we care about this affirmation of ourselves, including one study in which participants were even willing to pay for affirmation. How people treat us and what they say to us affirms us. When we are unsure of whether an important identity has been granted by others, our craving for affirmation becomes more intense and urgent. Psychologists call this a moment of self-threat—our identity is being challenged or dismissed.6 Just as moments of physical threat trigger a hyperfocus on self-preservation, moments of psychological self-threat do the same. If I value being seen as a do-gooder, then I feel self-threat when people judge me as a greedy person, based on stereotypes of my résumé. If I value being seen as a loving mom, then I feel self-threat when other mothers judge me for working full-time outside the home.

How to listen for the “shoulds” in your life

“Shoulds” are not only evil all the time. Some are instructive, some are helpful, some are reassuring when the timing is right. But in an environment of social media posturing, social signaling, comparison, and imposter syndrome, I’ve found that “shoulds” can veer toward the negative and are at the very least worth our attention.

I now have “should” radar, kind of like I used to have a grammarian’s ear for “can” versus “may.” (Apologies to all my friends who have heard me sound the “should” alarm.)

Listening for the “shoulds” is step one.

Not judging the “should” is step two.

I really like how these two should exercises propose options for how to sit with the “should” and figure out what to do next:

1. Ask yourself throughout the day "Am I doing this because I want to or because I should?" If it's because you "should," then "Why do I believe I should?" "What do I fear will happen if I don't do it?" Finally, notice if recognizing your choice as a "should" changes the choice itself, or the way it feels to carry out. Even if your actions remain unchanged, simply identifying your choice as a "should" or "want" is meaningful, and will help you know your true motivations and intentions and thus—know yourself.

2. Set aside a period of time (at least an hour every day) as a "should-free" zone—a time when you only attend to that which you "want." If anything shows up as a "should," set it aside for later or let it go altogether. If no "want" shows up, that's fine as it may take some time for a "want" to actually form inside you. Remember, "want" itself has become atrophied, like an under-used muscle. As well, sometimes the "want" is just to do nothing, so listen for that "want" as well.

Over to you

What are your biggest “shoulds” at the moment?

What do you do with them?

It’d be great to hear from you if this “should” essay resonates with you. You are not alone!

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About this newsletter …

Hi, I’m Kevan, a marketing exec based in Boise, Idaho, who specializes in startup marketing and brand-building. I previously built brands at Oyster, Buffer, and Vox. Now I am cofounder at Bonfire, a brand storytelling company.

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