Square Peg, Round Hole
Defined by Merriam-Webster:
a square peg in a round hole
noun phrase : someone who does not fit in a particular place or situation
| She felt like a square peg in a round hole at the new school until she made some new friends.
Have you ever been called or referred to as a square peg in a round hole? How did it feel to hear it? Who called you that and what role do / did they play in your life? Did the phrase resonate? Did it hurt? Did you wear it like a badge of pride? What was the round hole and did you wish that it suited you? Did you know that it didn’t?
Five years ago, when resigning from a corporate job, I was called “a square peg trying to fit into a round hole” and the following are my thoughts on it.
Writing I drafted after resigning from my “dream job” five years ago:
“Last week, upon sharing the news that i was resigning from my role and giving two weeks notice, i was referred to as a square peg not fitting into a round hole.
Blame my insecurities, upbringing, high standards for myself, brainwashing of a patriarchal and white supremacist society (there we go!), but when i heard this, i felt inadequate.
I proceeded to internalize the idiomatic expression as a critique of my skills, performance, leadership, contributions, communication, accomplishments...
That is, until i remembered that this was coming from someone i did not want to be. And that the ‘square hole’ i wasn’t fitting into is a publicly-traded corporate institution run by mostly white folks who care more about perception than anything.”
Recent happenings have prompted me to revisit this scene in the movie of me life.
Whether someone casually used the phrase in conversation, or I’ve shared the story of my career journey with someone, this memory has been stirred up more frequently in the last little bit.
So, I decided I can share more - about the memory, what it meant to me at the time, what it’s revealed to me now, and the changes that took place for the experience to evolve.
What it Mean to Me (at the time)
*closes eyes and time travels backward five years*
I’m living in LA and have decided to bet on myself as a freelance marketing consultant by leaving a toxic work culture in the rearview.
I’m giving a supervisor verbal confirmation of my decision after being put on a PIP.
Square peg, round hole. The words sting.
It honestly catches me off guard the moment it’s uttered.
The person is describing things about me that I know to be true - my tone does change when I get upset. I’m not a robot. Don’t human’s voices change when they get upset? or when they feel anything for that matter? Joy, excitement, stress, confusion?
So, when they tells me that I’m a square peg not fitting in, I internalize this subliminal message that I am the problem. Not the round hole. Me.
Logically, I know this not to be true. Not discounting my own flaws because I’m self-aware enough. Emotionally, however, it’s like any insecurity I’ve ever had is now at the surface, glaring at me, with the validation of these words.
I put in two-weeks notice and they pass relatively smoothly. It’s not until the laptop is turned in and the work comms are severed that I revisit these words. The confusion has faded.
The defensiveness I feel of my capabilities, intelligence, contributions, accomplishments and humanity. The injustice of it all. The expectation that capitalism was supposed to function in fairness at all. Especially for me.
And the frustrating empathy I simultaneously feel for those who’ve wronged me.
I’d spend months in therapy complaining about how this job impacted my mental health and somehow it still feels like a heavy weight on my shoulders. This healing takes some time.
About a year later, in 2022, John and I move to Austin, TX for his job and this very hard and healing chapter of solitude and clarity begins.
What it Means to Me Now (and the change it took to evolve)
*Fast forward to the year of our lord 2026*
When I look back on this written excerpt, I’m proud of me.
I laugh too, because 2021 Kaitlin didn’t name capitalism, but she witnessed first-hand the major problems with systems and corporations that externally act one way and internally operate in another way. The gross hypocrisy, the inauthenticity, the lack of integrity, the dishonesty, the misalignment with my values, the tension, the erosion of self-trust, the performative nature, the illusion. The lie.
She’s put these companies, their leaders and titles, and standards of success on pedestals for as long as she can remember, and yet is understanding of the fact that critiques from someone else only hold weight when you let them.
What people say about you hurts when you believe those same things about yourself.
In this case, I do believe myself to be a square peg, but what that means has changed for me. context matters.
The round hole is not my aspiration. Being true to the square peg and all if it’s dynamic nature, is.
I’m honest, curious, optimistic, hopeful, sensitive, tender, and have a practically nonexistent tolerance for bullshit. And in my own experience, the round hole is no place for these qualities.
The round hole is a carefully constructed system that required me to shrink, to offer up my time, energy, and peace willingly, to condense my spirit and disconnect from myself in order to “belong”. At the end of the day, what does it mean to “belong” inside of corporations that are loyal to the bottom line over all else?
The beauty of life is truly free will because I got to decide to remove myself (multiple times) from those environments. I’m not the first, I will not be the last and if I can do it, so can you!
Cheers to the wave of folks betting on themselves and building the world we want to be living in.
xx