Every year when this season rolls in, I can feel the old expectations creeping back in. Some loud. Most quiet. But all somehow convincing me I should be more, do more, feel more.
I should cook everything from scratch.
I should have the perfect home.
I should be ahead at work.
I should slow down. Speed up. Reach out. Feel grateful. Feel joyful.
It’s funny how a single word can snowball into a whole identity you never consciously signed up for. “Should” comes in looking helpful, but it often works like a subtle little weight. A brick you toss into your backpack until suddenly you’re wondering why everything feels so heavy.
I always say, “If a word makes you feel smaller instead of stronger, it’s worth questioning it.” And “should” is one of those words.
On the surface, “should” seems productive. It pretends to guide you toward improvement. But underneath, it usually delivers a very different message: You’re falling short.
Psychology research has backed this up for years. “Should statements” pull you away from your actual life and shove you into an imaginary version of who you think you’re supposed to be. And then, of course, it scolds you for not keeping up.
No wonder it’s exhausting. Every “should” is a tiny accusation. A whisper that says, Not enough yet.
And during the holidays, those whispers get louder.
This time of year has a way of stirring up nostalgia, old routines, childhood beliefs, and social comparison — a perfect recipe for internal pressure.
I should keep every tradition alive.
I should be happy even when I’m drained.
I should ignore my overwhelm because everyone else seems fine.
But here’s the thing most of us forget: half the “shoulds” we carry aren’t even ours. They’re inherited. Internalized. Leftovers from versions of ourselves we’ve outgrown.
The danger isn’t the word itself. It’s how invisible it becomes.
“Should” sneaks into your thoughts until even rest becomes a task you need to earn. Joy becomes something you need to justify. Worth becomes something just out of reach.
But the truth is simple: you don’t need to earn being human.
When you pause long enough to question the expectations you’re hauling around, something shifts.
You breathe again.
You feel space again.
You hear your own voice again.
Harvard’s research suggests replacing “should” with “could” or “I choose to.” Not as a motivational trick, but because it brings you back into agency instead of judgment. It turns pressure into possibility.
And possibility is where clarity shows up.
Start small.
Instead of “I should make every dish,” ask: Do I genuinely want to?
Instead of “I should be grateful,” ask: Can I let myself feel what’s real?
Instead of “I should show up for everyone,” ask: Who feels meaningful to connect with?
Instead of “I should rest,” ask: What kind of rest actually restores me?
The moment you turn a “should” into a choice, the guilt loosens its grip. The pressure lifts. The season feels human again instead of performative.
Before the whirlwind of expectations kicks in, take one honest pause and ask:
Is this something I want?
Or something I was taught I should want?
If it’s yours, honor it.
If it’s not, let it go.
The world won’t crumble if you choose differently. But your nervous system might finally take the deep breath it’s been waiting for.
Maybe the real gift this season is this:
Stop “shoulding” your way through life and start choosing the version of the season that actually feels like yours.
If you’re ready for a partner who approaches business with the same intentionality, less pressure more clarity — the team at StringCan would love to support you. Reach out, and let’s build something grounded, real, and aligned with what truly matters to your organization.