Ever notice how one little word can carry a lot of weight? For many of us, that word is should.
It follows us through our days like a shadow.
We should work out more.
We should be further along by now.
We should want to go to that social thing – even when we’re exhausted.
And here’s the sneaky part: most of these shoulds aren’t even ours. They’re internalized expectations and limiting beliefs we absorbed long before we had the self-awareness to question them.
They’re hand-me-downs. Passed along quietly through families, workplaces, and culture. Repeated so often we forget we’re allowed to question them. Over time, they shape our self-worth and identity more than we realize.
Lately, I’ve been paying attention to how often should shows up – and how much power it still has over how we see ourselves and our choices.
Are You Carrying Hand-Me-Down Expectations?
I think of shoulds like a heavy piece of luggage we’ve been hauling around for decades – packed with other people’s expectations and outdated beliefs about who we’re supposed to be. Inside are shoes that pinch and outfits that aren’t our style – but we keep carrying them because we think we’re supposed to.
Years ago, I had a moment that still makes me laugh. I was standing in the shampoo aisle at Target, completely paralyzed. In one hand: volumizing. In the other: moisturizing.
My brain short-circuited.
Should I want big hair?
Should I want shiny hair?
I was so used to looking outside myself for the “right” answer that I couldn’t even make a five-dollar decision. I walked out with nothing.
That’s what living by should does. It erodes self-trust and turns even simple decisions into tests of whether we’re “enough.” Every choice starts to feel like a verdict. We hesitate – not because we don’t care or don’t know – but because we’re afraid that if we choose for ourselves, we’ll get it wrong.
One of the gifts of midlife is perspective – and with it, the emotional freedom to question the mindset we’ve been operating from. We can finally see this baggage for what it is – and realize we get to decide what we keep, and what we set down for good.
Swapping Pressure for Power
The shoulds don’t magically disappear. But we can change how we respond to them.
These days, I’ve been practicing a simple shift: catching the should – and swapping it for language that actually belongs to me.
- “I should work out more” becomes → “I choose to move my body so I can feel strong.”
- “I should be doing more” becomes → “I give myself permission to rest.”
- “I should go to that event” becomes → “I intend to stay home in my sweatpants with a bowl of popcorn – and I feel zero shame about it.”
It might sound like a small linguistic tweak, but it changes the energy of your entire day. You move from being managed by expectations to leading your own life.
That’s personal growth in action – choosing autonomy over automatic patterns.
How to Recognize What’s Actually Yours
Notice where should shows up most for you – at work, in family dynamics, or in your own inner critic’s voice. Often it’s tied to people-pleasing patterns or an overactive inner critic.
Then notice how it feels in your body.
Does it feel heavy? Tight?
If it feels like a hand-me-down that doesn’t fit, you’re allowed to set it down – and choose authenticity instead.
Midlife isn’t about hauling someone else’s luggage. It’s about traveling lighter – with choices that fit you now, and make you feel like a million bucks.
What’s one “should” you’re ready to release – because it no longer fits the life you’re living now?
Try This: Become a Conscious Choice Maker
This week, start listening for the phrases that quietly chip away at your power:
“I have to…”
“I need to…”
“I should…”
When one shows up, pause and ask:
- Where did this belief come from?
- Is this actually mine – or is it someone else’s baggage?
If it’s yours, reframe it:
- “I choose to…”
- “I intend to…”
- “I will…”
Every time you flip a should into a conscious choice, you’re not just changing your words – you’re strengthening your confidence in midlife and rebuilding self-trust.
“I am not what happened to me, I am what I choose to become.”
— Carl Jung
About the Author – Making Midlife Funderful


Cheryl Dillon, CPC – Life Coach & Founder, Funderful Experiences
Cheryl Dillon is a life coach and founder of Funderful Experiences, home of Connected Hearts – a community of midlife women shaping a chapter that feels joyful, vibrant, and intentional. She also writes The Uplift, a nationally read newsletter blending storytelling, coaching, and humor to help women reconnect with themselves and each other – bringing more laughter, purpose, and heart to everyday life.
Cheryl’s work centers on the belief that genuine connection, meaningful experiences, and personal growth bring depth, happiness, and fulfillment to midlife. With a background in psychology and coaching, she brings warmth, insight, and real talk to conversations about friendship, identity, midlife transitions, and what it means to live fully and thrive in this season of life.
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