The Weight of 'Should'
- Tom Kenny
- Aug 30
- 8 min read

There’s this one word that can silently steer the ship without you realising. That word is should.
It creeps into our minds dressed as helpful advice, rational expectations, ego-boosters. But really, it's a sneaky little bastard. Sneaking through the back door.
It's the language of the ego whispering, “You should be doing this,” “You shouldn’t feel that”, “You should already have it figured out.” It sounds harmless. But it’s heavy. It distorts, weighs you down, wraps around you layer by layer.
I have this analogy I like to think of, which is that when we are born, we fall as a single snowflake from the sky. We are in some ways perfect, like the perfect crystalline structure of the snowflake. Perfectly symmetrical, perfectly proportioned. A consciousness untouched by the outer world. Just pure presence and innocence. We land on mount life. Our crystal is crushed (not to be depressing or anything), and so it begins…gravity takes hold, we are clumped to the other snowflakes we land on, and our descent unfolds.
Every interaction, every face we see, every action or conversation we have as we tumble causes more snow to clump around us. It packs layer upon layer until after many years we become this unstoppable boulder of snow and ice just hurtling down under the weight of gravity, not even sure what we are made up from.
In my teenage years, should filled layers of snow built up around me. It became the lens through which I saw nearly everything.
The avalanche of expectation
When I look back on my childhood and teen years, I feel real warmth. I had great friends and a supportive family. But nestled in those fond memories is also the truth that I didn’t know myself yet.
I hadn’t asked the questions. I was too busy performing, being who I thought I should be. Not out of deceit, but survival. Because the world tells you early: “You should act this way,” “You should like that,” “You should want more.”
You just want to fit in don't you? You just don't want to be that weird kid that people don't want to hang around with.
The power of should. God, what a word. So quiet, so casual. But so heavy. A word of suggestion that sounds like freedom but comes loaded with rules.
In my eyes, should is the voice of the ego, and my ego has always had two jobs: To keep me safe, and to elevate my status.
I went to school with lads who I think it's fair to say were early bloomers in the romance department. Chasing girls, experimenting, I joined in of course, that was the unsaid expectation set between me and me. And let’s be real - it was exciting. Firing up the testosterone engines, Snapchats flying, hoping for a bit of weekend smooching. But when it came to true intimacy, some gentle fumbling, hands wandering…something didn’t feel quite right.
Inside my head I thought “You shouldn’t be uncomfortable.” “This should be easy.” “This is what boys do.” “This is what girls want.” “What’s wrong with you?”
Looking back, I was just young. Too young. Not ready. I was fifteen, for crying out loud. My voice was just about to descend to the frequency range an adult could hear at. But at the time, I felt ashamed. Like I was broken. I felt like this meant I wasn’t a ‘proper’ man, and that I wouldn’t fit in or be liked or whatever other BS teenagers think.
The real issue? Expectation. I wasn’t approaching those experiences with curiosity or openness. I was approaching them through the lens of should. This is how it’s supposed to go. This is what it should feel like.
Should is the ego’s favourite tool. “You should go to that party.” “You should try this.” “You should speak to her.” “You should want this.” “I should say yes.” “I shouldn’t feel that way.” “He should respect me.” “They should notice me.”
Every one of those “shoulds” comes from expectation. Expectation of yourself, of others, of how life is supposed to be.
Ultimately, expectation is the killer of joy. Maybe not in a dramatic, murder-y way. But slowly, over time, expectations nibble at your contentment until you’re left hollow and unsure of what really makes you light up.
Beneath the layers of ‘should’
At university, I had a few moments, or more accurately, a series of moments, when I began to understand who I really was. Not who I thought I was supposed to be. Not who I had been performing as.
I didn’t really clock any of this until the pandemic. That strange, eerie stillness peeled back the layers. Without the noise of social obligations, I finally heard the thoughts behind the thoughts. The expectations behind the actions.
It’s going to sound strange, but I am so, so grateful for the pandemic. I think it saved my life, well no, it definitely did.
From about the age of 15 up until the pandemic, I think I would describe myself as floundering. Outwardly fine. Generally having a good time. But inwardly? Caught in loops of self-destructive thinking. My snowball by then was enormous, messy, dense, maybe even chemically enhanced (thank you, Leeds nightlife).
The day we all left Leeds sticks in my mind. Suitcases stacked on doorsteps, leopard print blankets being bundled into the backs of Fiat 500s like kidnapped children. It felt apocalyptic. Alien invasion vibes (I wish) minus the flying saucers landing on the Thames. Just a creeping sense that life was about to change in ways we couldn’t understand.
I was a social guy at Leeds and had a really close-knit group of friends for whom I have a lot of love. What was I going to do without them? That year I felt like I had started to understand myself more. What made Tom tick? I’d just started to feel like I was uncovering a version of myself. I was DJing, something I’d always wanted to try but hadn’t had the guts to do until now. I’d been immersing myself in the Leeds music scene and was just absolutely obsessed with electronic music. It felt like this great foundation was about to be ripped away.
Two weeks before we all left, I had tried a small dose of psilocybin for the first time at a friend's house. I danced, laughed and felt love like I never had before. I felt like I was listening to music for the first time again. It was like some little being had climbed down my ear canal and started caressing my eardrums. I felt free. Unshackled from the chains of expectation I had contained myself within. Free to express myself however I damn pleased. So where was I to take this newfound sense of self when I was locked in my home?
Stripping.
No, I didn’t become a stripper (sorry to disappoint).
I’d somehow ended up as a self-employed gardener (don't ask), so I’d throw on my work gear, hop in the VW polo and be out to tackle overgrown hedges all day.
April to September 2020? Peace. Pure peace. Like some medieval peasant dream. It really stripped back those layers of protection and survival I'd built up year after year.
My days moved slowly and really grounded in something real. I’d wake up, have a coffee in the garden, and watch the birds dance through the trees. By 4, I’d be home. Yoga. Dinner with the family. Evening music production session or a little spin on the DJ decks. Then if the weather was kind, a walk to the beach and chat nonsense with three of my close mates. 2 metres apart of course…
That was the closest I’d felt to feeling right. Simplicity, safety, presence. A tiny, trusted circle. No pretence. No pressure. No shoulds. Most importantly no people I was just hanging out with out of habit rather than intention.
But then like a pin popping a balloon, the world reopened, and all the shoulds came rushing back.
“You should see this person”. “You should be more social”. “You should chase this opportunity”. “You should be grateful”. “You should move forward”. But that version of me, the one I found in the simplicity, he didn’t want to move forward. He wanted to retreat. To curl up somewhere quiet. To hold onto that peace. So, he did.
Breaking point
I ended up becoming a bit of a recluse, I wanted it all to go back to being simple and easy. I started to fight the tide, and it wasn't going well.
At this point I slipped into depression. I felt absolutely hopeless. I felt trapped. Frozen by anxiety. Gripped by fear and regret. Who the hell was I until the last year? Was I even a ‘real’ person? Or was I just a pretender? I felt like I had been living a lie. It was horrible.
One night, I was driving home after seeing a friend. I’d felt on the verge of tears all day but kept it together, wearing that familiar, forced smile. “You said you’d go, so you have to now.” Classic Tom. It must have been 9 at night, a huge lorry was rolling up this road towards me, headlights cutting through the dark, and I had this sudden urge…should I?
I didn’t.
But the fact that I even considered it... that’s just how low I was.
I’ve heard that humans fear 3 things: death, other people, and their own mind. It's fair to say that the first two I had been well aware of. But now, my own mind was definitely in pole position. I needed help, big time.
The next day I spoke to my parents. They’d known something was off for a while. I told them everything. No filter.
They were absolutely amazing about it. Unsurprisingly.
I had always had a wall of untruth between me and my parents. So many white lies, just to try and keep them happy and keep them from worrying. However, in that moment this wall was torn down like it was 1989. “Mr Kenny, tear down this wall!”. Good old Ronald Reagan.
I started talking therapy to make sense of this existential crisis I was in.
I’m surprised I didn’t transform into a large hairy white raisin the amount I was crying, but I got it all out. I felt what I needed to feel. I then started to pick up the pieces and put back together who I was and who I wanted to be, slowly but surely.
I started to try other things too in the space of yoga, meditation and the likes on the recommendation of my mum. I found the Ten Percent Happier App which honestly has been such a huge influence on how I have thought about my personal values and who I strive to be every day.
There’s a teacher on there, Joseph Goldstein, who I am so grateful for. I learned about attention, distraction, stillness, states of mind, attitude, judgement, anger, fear, other emotions and how they appear in the body. I started to really get to know my own brain as if it were my wardrobe with the different outfits for different occasions.
My anxiety massively reduced. The enjoyment and peace I was getting from life quadrupled. I felt alive. I was there.
Many things have saved my life and continue to save my life. We pick up these practices that help us, and sometimes complacency kicks in and we have to re-adjust and come back to our centre. I know I often do. It is so important to try new things. The brain is often trapped in a yesterday ground of negativity. The ego craves recognition and status, but it also craves comfort and ease. It’s a tricky balance, and maybe we never quite get it right. But trying to get closer, that’s the point.
Most importantly of all, don’t forget to live.
When I’m stressed, low, or anxious, my default is to ditch rest for self-help. I swap stillness for striving, convinced I need to fix myself or get back to some imagined better version. But the truth is, there is no going back. There’s only forward, and if that’s the direction we’re headed, we might as well try to enjoy the ride.
Which brings a nice close and ties up the message of this blog.
Live your fucking life people!
Don’t spend life being someone you’re not, be who YOU want to be. One day, that snowball will stop at the bottom of the mountain, and melt.
On that cheery note. Toodaloo.




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