Published September 9, 2021, updated June 1, 2026

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You should be making your creative work every day.

You should be spending more time with your family and friends.

You should spend a lot more time selling your work.

You shouldn’t have to sell anything: your work should speak for itself.

You should give up. Who do you think you’re fooling?

Did any of those statements make you feel guilty, or angry, or…did they maybe make you feel seen?

I’m sorry. I didn’t mean to fuel that awful voice inside your head. Because I know you probably say stuff like this to yourself. Just about everyone I’ve ever met does. This is a loop that plays on endless repeat, like an awful commercial jingle, for the vast majority of creatives.

It’s exhausting and demoralizing.

So I get it, it’s natural to want to “silence your inner critic.” I googled it, and can confirm: people want to “overcome,” “conquer,” “master,” “dethrone” (love that one!), and “tame” their inner critic.

No one’s looking to “befriend,” “understand,” “empathize with,” or “comfort” that nasty voice.

Yet, that’s exactly what you need to do in order to turn down the volume on all that criticism.

When I started coaching, this came as a complete surprise.

In the very first run-through of the Creative Focus Workshop, in my very first lesson, I asked students to choose a single goal to focus on. Instantly, they started to spiral, sharing how many ideas competed for their attention, and how they felt like they should be doing all of them.

In solidarity, cartoonist Sarah Leavitt posted this little homunculus she’d hung above her desk to take the blame for all the nasty things she said to herself. When she shared it, the crowd, as they say, went wild. Everyone identified with the feeling that there’s some beastly monster inside, constantly running you down and trying to hold you back.

Thus, the Should Monster was born.

So then I had everyone draw their personal Should Monster. My one rule was, I don’t want to hear “I should be able to draw better.”

Staring into those ugly faces, it finally sank in for everyone: We all struggle with these thoughts. And once you externalize the voice of the Should Monster, once you give it a face, you can start to understand what it wants with you. And then you can begin to turn down the volume.

What is the Should Monster?

The Should Monster is the personification of the inner critic, that self-punishing voice that tells us we should be better at everything and stop screwing up, and by the way, do it faster. Shoulds are the engine of perfectionism: the constant stream of creative self-doubt that undermines any action.

As part of the Should Monster exercise in the Creative Focus Workshop, I have students make lists of all the beastly things they say to themselves all day as their inner critic tries to force behavior change via abuse. (Never works.) Then they create a depiction of their personal Should Monster.

Here are just a few.

Where does the Should Monster fit in the Creative Engine?

The Should Monster is one face of the Reflect phase of the Creative Engine, the mirror image of the calm, reasonable rhythms of reflection where you (in theory) look back at what you’ve done and learn dispassionately from your successes and failures, using that insight to chart your strategic next steps.

It would be great if reflection were always so considered and meditative. But let’s be real. Thinking about what you did and didn’t do, what worked and what didn’t, what you finished and what you wish you’d finished, that’s a huge trigger for Shoulds.

Why doesn’t a great plan make the shoulds go away?

When you make a solid plan to see a creative project through to the finish line, it seems like checking off the boxes should be straightforward. (There’s that Should again!)

☐ Draft outline
☐ Finish first draft
☐ Revise
☐ Publish

Yeah, not so much.

Back when I started teaching Creative Focus, I believed that getting ambitious projects done all came down to systems and planning. And of course, you definitely do need (your own unique and personal) systems and planning.

Very quickly, however, I figured out that lack of systematic planning is only a part of what holds most people back. After all, if you could just slot a system in and have it solve everything, then those dozens of productivity apps and hacks you’ve tried and discarded would all have worked, and we would not be here today.

No, the forces holding most people back are emotional. Some of the most talented—and most productive!—people I know suffer deeply every time they sit down to continue making their work. They have a hectoring voice in their heads that yells at them about everything they “should” be doing, and everything they’re getting wrong. In particular, whenever we take creative risks, those inner critics come out to howl.

Unfortunately, both running a business and creative work involve quite a bit of risk, and so are reliable triggers for negative self-talk.

But one of the most important things I’ve realized while exploring Shoulds is that this voice is there for a reason: it’s trying (misguidedly, in a short-sighted way) to protect you.

We’re going to start sorting your pile of Shoulds into three categories. So you need a pile to sort. Grab a piece of paper and write down every Should you hear your inner voice nagging you about. And it doesn’t need to actually include the word “should” to count! Any type of correction or self-criticism counts.

The 3 categories of Shoulds

One of the key insights I’ve gained over the years talking to students about their Shoulds: they sort into three piles. Wills, Want-To’s, and the ones that are still, stubbornly, just Shoulds.

Of course, they’re all painful. Whenever your lived behavior and your idea of what your behavior should look like don’t line up, it’s hard. But there’s a large category of Shoulds that are actual ambitions that fall on a spectrum from “that would be kinda nice” to “this is life or death.”

Is it a Should? Or is it a Could?

Much of what your inner critic frames as a Should is actually just a Could. It’s something you noticed, found compelling for your own reasons or due to external influences, but then never took action.

In the domain of health, real-world examples might range from “I should add sunscreen into my morning routine” to “I should stop eating red meat because I have major heart disease risk factors.” These Shoulds come from things like reading articles, comparing yourself to other people (or, to other people’s polished public personas), and stuff your doctor tells you.

You absorb some new information, and you think, ooh. That really would be a good idea. But then you don’t actually take action, bang-presto: you’ve taken on a new Should.

There are a few problems with these Shoulds, besides their shouldiness.

1. The fact is, some Shoulds are really serious and necessary ideas to implement. Some are true ambitions for how you want to live. Others are just “nice-to-haves.” The difference between these often gets obscured.
2. There are way too many of them. You could not possibly implement all your Shoulds into behavior change, even if you wanted to. You have to choose, and that means facing the pain of admitting to yourself that there are changes you will NOT make (not now, and possibly not ever).
3. The ease with which they crop up again. I wish we could just quit reading self-improvement articles, but that’s not happening. Just try to be aware when a new wish starts curdling into a Should!
4. The biggie: the fuzziness of Coulds that look like Shoulds. You “could” do lots of things. There are always new shiny ideas to pursue. (So bright! So pretty!) But just because you’re great at generating ideas doesn’t mean you need to follow them through!

Back in that first CFW class, writer Susan Olding responded to Sarah’s homunculus with her own fairly epic list of her painful Shoulds.

Your list might be shorter or longer than Susan’s. Either way, you can’t address it as one undifferentiated pile. You need to sort.

I call the first two categories of Shoulds Wills and Want-To’s.

The good news is these two categories line up, more or less, with what you actually want for your life. They’re also easier to resolve than the third kind. In other words, these stay Shoulds only until you pull them out. Once you do, your list gets shorter, and what’s left will be easier to parse.

To make a Should into a Will, you simply need to decide to take action, and then start building a tiny habit. Caution: before you tell yourself you’ll take on a new habit, take a pause and make a conscious decision about whether you will do this, and do it now. In the Creative Focus Workshop, we do this by calibrating the space you have available for new habits and projects based on your 3 Cs: Capacity, Criteria, and your other Commitments.

Short version: Don’t tell yourself you’ll do something that you simply don’t have the capacity to follow through on right now. That will put you right back at square one with the same old Should.

A Want-to is a Should that you’ve considered, decided really is something you want to do, but acknowledge that you don’t have space for it right now. That helps, too. When these pop up in your mind (and they will), just remind yourself, “Ah yes, I do want to do that. But I don’t have the capacity right now, so I’m not working on it currently.”

This was what André Hedetoft, a Creative Focus Workshop student, did when he came to this exercise. He’d been carrying a punishing list of Shoulds, but he realized that some of these nagging thoughts really were things he wanted for his life, like “journal daily.” As a film director and dad of 3 small kids, he didn’t have time to implement that idea immediately, but that didn’t mean he shouldn’t, ever. So he literally sorted his list into Wills, Want-To’s, and…everything else.

He said:

I absolutely loved this exercise. For me… life transforming.

One of my biggest problems is and has always been that I’m genuinely interested and curious and just love to turn anything that captures that brief attention into really big projects and massive plans. It starts out well with great momentum, but then reality sets in and I have a hard time following through, which turns all those “wants” into shameful “shoulds.”

André pointed the way to a sharper methodology to actually deal with Shoulds. Because once you have a list…what are you supposed to do with it? I revised how I taught the Should Monster to incorporate this tool.

So step one to dealing with your Shoulds is to sort out your list. Which are things you will do, now? Which are things you want to do but aren’t doing yet? Pull those out, and watch how much shorter the list gets. It also gets more concentrated and challenging.

A snag you’ll hit while sorting: dilemmas

Some of your Want-To’s will collide with each other. You’ll find one Should that tells you to do a thing, and another that tells you to do its opposite. And when you look closely, both could be real want-to’s. That’s a dilemma: there are two things you want, and committing to one means giving up the other.

Susan Olding’s list of Shoulds included many that were mutually exclusive.

• “I should be writing a LOT every day” vs. “I should be writing less but better — perfect little nuggets of deathless prose.”
• “I should refuse all social engagements until I have finished my big project” vs. “I should attend all writing-related social engagements even if I don’t feel like going because that is part of being a good writerly citizen.”
• “I should make my work more mainstream” vs. “I should make my work more experimental.”

Susan could see herself pursuing either direction in any of these, and if she failed to surface these inner contradictions and make clear decisions, that compounds the problem. A dilemma keeps you from committing to not just one, but multiple Shoulds, and sets up a situation where you, by definition, are failing at both.

The only way out is to decide. Which priority comes out on top right now? What fits your capacity in the present moment? Pick one, and declare the other a Won’t. You won’t do this thing. Of course you’re allowed to change your mind. But either decision puts you in charge, rather than remaining suspended between options. Not deciding will leave you procrastinating endlessly, because you’re not even really sure what you want.

Then there’s what’s left.

Commit to the Wills, park the Want-To’s, decide the dilemmas, and you’re left with a residue of the hard kind of Shoulds that won’t go away no matter what you decide. Like some of the other Shoulds on Susan’s list:

• I should finish my novel or a work of narrative nonfiction so I can actually have a real career vs. what I have now.
• I should just stop trying to make art at all because who do I think I am, anyway?

This kind isn’t really about writing every day or going to grad school. There’s something underneath them, and that’s what we’ll look at next.

What’s behind that curtain?

Now it’s time to talk about the “monster” part of the Should Monster: the Inner Critic, that unreasonable, cruel, demanding voice that runs amok at the worst possible moments of vulnerability.

That’s the key, of course: vulnerability. Because the Should Monster isn’t really a monster at all…It’s like the Wizard of Oz. It throws up a big, nasty, threatening show because the reality is, those are your fears behind that curtain.

Your atavistic survival fears fuel the Should Monster

We’re all semi-hairless bipedal primates here. And we were able to evolve our wonderful big creative brains because we’re also wonderful at creating social bonds. On the African savannah, community was literal survival.

Your brain is programmed at a primal level to survive and procreate. That’s it. That deep level of biological function is completely indifferent to whether you publish your magnum opus (although, arguably, that could be considered a play for immortality).

On top of those evolved guardrails, you’ve been disciplined, socialized, and in plenty of cases gaslit into conflating staying safe with a tangle of social and cultural rules that have nothing to do with outrunning lions.

Parents, school, culture, the whole apparatus teaches you what “safe” and “acceptable” look like. Aligning with gender norms, the right kind of job that conveys status, joining sports culture, whatever it is. Your ancient firmware has been hacked to slot you into social acceptability according to our late-stage capitalist hellscape.

/rant-over

In short, Shoulds are your nervous system trying to keep you safe. But using 80,000-year-old goggles, and blunt-instrument tactics.

How that ancient firmware hack gets installed: Trauma and control

The savannah-programming-plus-late-stage-capitalism theory tells an overarching story. But it doesn’t tell you why the volume of your particular monster is calibrated the way it is. Why does this Should hit so hard, and that one barely registers?

Your unique set of Shoulds stems partly from specific people, in specific moments, expressing their own fears by trying to get you to behave in certain ways, drilling specific rules and expectations into a younger you. That’s how the shape of your Monster developed. Someone else’s anxiety got spackled onto your firmware until your own threat-detection system enforces it without their needing to be in the room anymore.

In 2021, I invited Nicole Lewis-Keeber on the Autonomous Creative Podcast to speak about emotional sustainability and the importance of boundaries in our work. Nicole is a former clinical therapist who now works with business owners to unpack their relationships with their work. Pretty quickly, our conversation turned to the inner critic.

Here’s what she said:

I think the inner critic is very much wired, connected to our nervous system, in that our nervous system is set up for survival […]

I don’t think that we should “exile” our inner critic. I think that there’s information there for us. There’s usually some younger version of ourselves that has been wounded in some way that needs some attention when that critic comes up. I think our inner critic is the protector of those younger versions of ourselves.

If the inner critic is a trauma response, then it’s protecting a part of you that’s been hurt before. It’s trying to prevent you from getting hurt again.

Your Should Monster is going about it all wrong, of course. Berating and belittling you, attempting to use shame as a tool for self-control, will backfire. Nonetheless, that monster is sitting on the exact information you need so that you can take care of yourself and heal.

What can we do with this information?

Instead of shunning your inner critic, you need to tune in to it.

When students share their depictions of their Should Monsters and what sort of “inner critic garbage” it berates them with, let me tell you, they sound exhausted.

Not just the students, but the inner critics, too.

We are tired of hearing about how we should be writing our tenth book already, and we are tired of spending all of our energy trying to silence that voice and shut it down. And our inner critics are tired of screaming for our attention. They truly think they’re protecting us, and they’re just as scared and exhausted as we are.

To break the cycle of anxiety and procrastination, we need to listen to our inner critic.

Trying something new can lead to, “I’ll never be able to pull this off. I should go back to school and get a grad degree.”

Promoting your work can trigger, “Everyone will hate me. I shouldn’t put myself out there.”

These Shoulds reveal consistent and completely understandable root causes:

1. Wanting to be loved and valued (and fearing you’ll lose love or esteem because of something you’re doing or not doing). This can lead to Shoulds like “I should make sure everyone around me is OK before I take time for my own work.” That can grow from a history where asking for what you needed got you punished, but being useful, available, the one who handles things, kept you safe. So now, decades on, prioritizing your own work feels like making yourself a target.
2. Wanting to be safe from criticism (and fearing that any deviation from the “norm” will cause you to be ostracized or even put you in physical danger). Hearing your inner critic needle you, “This work is crap, you should keep it to yourself,” can stem from traumatic experiences of criticism of your creative efforts in school or at home. That voice is trying to keep you from taking a creative risk…before it’s too late and you get hurt again. This is a huge contributor to perfectionism.
3. Wanting to reach an ambitious goal (and fearing that missing any step, on a timeline your brain has decided is the objective standard, proves you were never cut out for it). Better to quit now, the monster tells you, than to risk failing in front of everyone and losing #1 and #2 in the bargain.

You’ve been told, over and over, by people in your life and from every aspect of our culture, what “safe” looks like.

You know you don’t want to live in alignment with that ultra-cautious, even retrograde version of “safe.”

Yet, when you dare to want anything, you open yourself up to the pain of not getting it. When you act towards the goal of what you want, you risk even more pain. Your fears will rear up and try to box you back up into the safe zone in an equal and opposite reaction.

Your inner critic will try to protect you.

I get this. It makes sense.

Perhaps seeing how it makes sense is the first step to unwinding it.

How to talk to—and listen to—your Should Monster

Here are a few ideas for how to start connecting with your should-iest Shoulds.

Identify your inner critic

Try to identify how old it seems to be, whether it’s tied to someone you know from your past, like an ex-partner, a parent, or a teacher. What does it look like?

When she explored the voice of her Should Monster, Lynna Goldhar-Smith found her third-grade teacher. Decades later, that teacher’s voice is still in her head, telling her she’s not supposed to be drawing.

Take some time to figure out when it usually shows up. Does it fire up its engines when you make a little mistake? Maybe it’s when you’re halfway into a new project and all of a sudden there are a ton of unknowns.

This is the emotional underbelly, and it’s going to be tough, but you need to get clear on this so that you’re prepared to talk to it when it slips through the crack in the door.

Yes, talk to it.

Ask your inner critic some questions

The inner critic is almost like a parentified child. It had to grow up way too soon to protect you from the thorny barbs of reality, but all it’s managed to develop are maladaptive coping mechanisms.

When it speaks up, say, “I hear you, what do you need?”

Show your inner critic some empathy. Ask what it’s trying to tell you. What is it afraid of when it tries to stop you from doing The Thing? Or when it starts telling you about all of the things you should have done by now?

You don’t have to follow its directions. You can acknowledge the answers it gives you, and learn from them. When you access your inner critic and give it space and self-compassion, it will be more likely to ease up on you.

Slow down, ask, and breathe. When you stop trying to overrule that voice, you’re likely to find a little bit of wisdom about something that needs to be healed.

Learn to respond to your inner critic

This is a personal process, and it will take time. But the goal is to stop living reactively, where you’re either fighting the inner critic or frozen by it, and start having access to your creative work and a consistent practice.

1. Try addressing your Should Monster directly, by your own name. It sounds odd, but it’s been shown to lower anxiety. Ethan Kross, who runs the Emotion & Self-Control Laboratory at the University of Michigan, studied what happens when people coach themselves through a high-pressure task (giving a speech on almost no prep), using their own name or “you” instead of “I.” Kross found that the people who talked to themselves this way performed better in front of objective raters, felt less distress, and spent less time afterward ruminating over how it went. Example: “Jessica, I know asking for help feels scary. What if she says no? Or worse, what if she says yes but resents you for it? But remember—she offered to help. And you’re always there for her, too. Instead of hiding, how can we make sure you both feel valued?”
2. Get specific about your fears and create a contingency plan for if things go wrong. By mapping out these potential challenges and solutions, you can feel more prepared and less anxious about taking that leap. For example, if you’re worried about your friend getting mad when you ask for help, take a moment to think it through: “Okay, Jessica, so what if she does get upset? What’s your next move? Maybe you could write her a heartfelt thank-you note afterwards. Or perhaps you could set up some check-in points along the way to make sure you’re both feeling good about the process. Worst case scenario, if this causes a major rift in your friendship, that would be really painful. Let’s figure out who you might turn to for support.”
3. Pretend you are your own best friend. What would you say to someone you love? Would you say to a friend, “What an effing slacker! What the hell are you doing?” Not likely. Instead, you’d be supportive and try to help them calm down and address the problem at hand: “Jessica, you’re procrastinating. That means you’re trying to avoid something. Let’s take a beat and figure out what’s going on. Don’t worry, you’re going to be fine.”
4. Care for your younger self. Your Should Monster often represents a younger, less experienced and less powerful version of yourself. Think about who this version is, how old they are, what they are remembering and reacting to when they lash out. Can you take on an adult role and, knowing what you’ve learned over time about what you’re capable of and the likely outcomes of your actions, comfort your younger self to help them calm down?

You now have a more concrete idea of who this critical self is, which means you have a real place to direct your self-compassion. Respond to it with warmth rather than reflecting the negativity back at it or retreating into yourself.

The next time you feel the physical signs that this part of you is trying to tell you it’s afraid—tightness in the chest, the first flutters of anxiety, increased heart rate, or just the heavy dread of knowing that the verbal abuse is about to start again—tap into it. Resist the urge to try and silence your inner critic. Recognize what’s happening and acknowledge the fears. Calm will become easier with practice.

A note on getting mental health support

I am not a mental health professional, and none of this is a substitute for working with one. Learning to handle your Should Monster with some compassion is something you can practice on your own, and it can help. But if any of this opens a door onto something bigger than you want to face alone, a good therapist or counselor is a real partner in navigating these choppy waters.

Why this matters

Compassion towards your inner critic will allow you to make decisions for yourself based on your goals, and not your fears.

The point of visualizing your Should Monster and sorting its demands isn’t just to feel better in some abstract way. It’s to help you free up more capacity for your actual work. Every hour spent stewing in I should have, I should be, who do I think I am is an hour not spent making the thing. Every shame-tainted project is one you’ll avoid, even if it’s actually what you most want to do.

Writer Jen Pinkowski chose photography rather than drawing to depict her Should Monster. Her vivid image addresses the way carrying these Shoulds over the long term felt like it was deforming and ultimately endangering the very survival of her creativity.

You don’t have to win the argument with your Should Monster. You don’t even have to have an argument. You can reduce the list, turn down the volume, and treat this fearful part of you with kindness. All of that can help you get back to your real work.

Switching from trying to fight and beat and silence your inner critic to listening with empathy is tough. But the Should Monster holds valuable intel: which old hurts are causing you to freeze up (that you can now let go of)? Where are you holding on to multiple options because you haven’t trusted your own decisions and instincts? What do you really want to commit your capacity to, and what are you holding open just in case (while it drains your bandwidth)? The Should Monster is not exactly your ally, but when you pay attention, it points the way out.