You Can’t Always Pull Yourself Up By the Bootstraps

But you can find a different battle worth fighting

Jayla Sun
Jayla Sun
Jun 13 · 8 min read
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Photo by Tommy Lisbin on Unsplash

We think we have control over our fate. That’s why we try so damn hard at everything. We think that perseverance, grit, and determination all play a large role in our life’s outcome. And that’s why we’re bound for disappointment.

In college, I sent out nearly a thousand cold emails looking for summer jobs. Yeah, that’s right. Jesus, take the wheel? No, I’ll take the wheel from here — thank you.

I ignored the fact that most of my emails were ghosted and many of them were politely rejected.

The two measly offers I received were enough to convince me that my brute force bull’s determination was what got me there. It had nothing to do with sheer luck and bad probability, I told my self. Boy, was I in for a rude awakening.

See, I was the brown-nosed intern. Before my first day, I printed out all the onboarding documents sent to us. I really do mean all of them — the “Welcome!” pamphlet, the workplace safety powerpoint, and the payroll calendar. I also dated, signed, and organized them all in a duotang folder.

Sheer will and determination was what got me there. And I believe that it would bring me to the top.

On my first day, I put myself in a tunnel and vowed to focus on the work in front of me. Those who work hard are rewarded with success, right? And the harder you work, the more you succeed, right? I just needed to have the discipline to plow through my responsibilities. Wrong.

Wrong, wrong, wrong!

And that’s not how it turned out. That’s never how it turns out.

It started with a meeting. All the interns piled into a tiny little conference room to one by one present our biweekly updates. Days before, I fiddled with the formatting of my powerpoint and rehearsed my script for way too many hours. And my talk went well, but I couldn’t help but notice how our boss just beamed at Andrew’s presentation.

That caught my attention. Who is this Andrew kid anyways? That presentation didn’t blow my mind.

As I walking down the hallway back to the students’ office, I heard the boss joke casually with Andrew. Wait a second, what the heck.

Now I was concerned with more than just getting my work done.

Andrew was now on my radar. He was stepping on my territory, eating my Halloween candy!

So, like every maniacal, obsessed freak, I started to take careful note of everything Andrew was doing. If I wanted his success, I needed to first understand where our differences were.

What I found was infuriating.

He wasn’t the humble superstar I anticipated finding. He was everything but that.

Andrew waltzed in just before noon most days. He had his shoulders pulled back and a careless grin on his face. There was no anxious urgency to get started on work.

Mostly, he just looked around for someone to chat with. It seemed pretty innocent. And that just made me more angry.

Then if no one paid attention, he would sit down and sort of pout, like when a child can’t get anyone to play with them. Boo hoo, the rest of us had work to do — real work to do.

He spent most of his time carefully picking out a song on Spotify. Then, he’d refresh his email for the umpteenth time and when there was nothing (there was always nothing), he’d watch some sports on YouTube. If the stars aligned that day, he might have opened an excel sheet to do a bit of work. But that was really pushing it.

After less than an hour of barely doing anything, he would stand up and decide he deserved to go for lunch.

Since I worked at my desk so often, I realized he usually left for almost an hour — nearly double the allotted time!

Then returning from his break, he’d sit down for a few hours and repeat the the mindless routine. I guess three hours of doing nothing can get pretty exhausting because he’d leave early almost everyday.

I was really irritated, but also mostly confused.

What I would learn later in the summer was that Andrew was the son of our boss’ friend.

He didn’t apply for the internship. He didn’t create spreadsheets to track places he’d sent applications to. He didn’t refresh his email every second of the day hoping that someone had responded to his carefully constructed email — even if it was just another rejection.

He was handed the position. Maybe his parents even begged him to come to work. Or bribed him. Because they knew this would be good for his future.

Either way, it was like a 1000 piece puzzle just fell from the sky and right into place. It made so. much. sense.

After that I have to admit, I spent a lot of time hoping that his privileged, underground route to success would light up in fire and crumble under the flames.

Sometimes, I even tried to devise plans on how I would upsize him. But that was fruitless, of course.

I wasted a lot of time complaining about how unfair it was. But that didn’t help.

The whole thing made me feel kind of foolish. Like somehow I had taken the long, arduous journey to get to the top of the mountain. Then when I pulled myself over the edge, I’d see him standing there pointing to the very obvious cable car that would have made the trek much, much easier.

But of course, I didn’t have access to the cable car. That was an exclusive perk. A membership you could not buy.

And the worst thing about all this was, my arguments were all valid. Everyone I complained to agreed that nothing about this was fair. But that didn’t help either.

Why? Because that’s just reality.

We like to pretend we reward people for talent and hard work. And sometimes we do. We also put those things in the news. Like “Indigenous Student gets Accepted to 12 Ivy League schools” or “Small Town High School Sends Immigrant Students to Elite Colleges”.

When these things happen, we shout it from the rooftops because we want to show the world that we are working towards a meritocracy. That everyone has equal opportunity.

And maybe we are working towards more equality. But we’re not quite there yet. What those headlines really show us is that these things are rare. That’s why they gather so much attention on the internet.

The truth is that background, connections, and good old nepotism all still play a large part of our society’s decisions.

And we know it’s wrong. That’s why we’ve gotten really good at disguising it, concealing it, and covering it. It’s also why things like last year’s college scandal blow up in the media and come as a shock.

But passing down the privilege is a habit that perpetuates a nasty, vicious cycle.

Like if you had to fight and claw your way into a higher position, you’re going to use your power and advantage for your loved ones. Because why the hell not? You earned it, right? You had to watch others take the easy route while you laid down cement with your bare hands. It was the only way you could make sure you didn’t fall through the cracks.

And if you were a product of this underground club, you want to stay there. It’s nice and cozy and there’s sparkling water in the reception. And this messed up system — well, works. That’s part of how you got where you are. So, you keep letting your family, your friends, your children take that route.

But that makes the divide even wider. Those who on the privileged side have it easier and easier. And those who are less fortunate have it harder and harder.

They say the apple doesn’t fall too far from the tree. We see this all the time. Calvin’s parents are accountants and Calvin becomes an accountant. Thomas was raised by drug addicts and grows up in a rough neighbourhood and decides that college isn’t worth it. Stephanie comes from a long line of doctors and Stephanie gets into medical school.

Sure, sometimes it’s because they were “inspired” by the previous generation. Or maybe I’m reading your college application. Yawn. Tell me a story I haven’t heard yet.

That’s just life. It sucks, it hurts, and it burns. It also took me almost four years to figure out what to do about it.

There was no ah-ha moment. The story doesn’t rope around with a brilliant plan for us lay people. At least not for most of us.

Here’s the thing. I just left.

When my contract reached its’ expiration date, I packed my things, thanked them for the riveting experience, and just left.

And that was hard because the place had a great reputation. It looked so good on my resume. It felt so good to say at dinner parties. It just glistened on my LinkedIn profile. And I was just starting a career. Those things were hard to leave.

I also earned my right to be there.

But I knew deep down that a place that lets things like that happen isn’t a place I want to stay long term. Sometimes big name companies and fancy titles are like pretty faces with empty souls.

You can’t help but gawk at them from a distance. They inspire so much jealousy in everyone around you. And you want people to be jealous of you. But it’s until you get it, that you realize that it’s not as good as it looks. It’s never as good as it seems.

See, these places start off as something really amazing. That’s how they build their name.

But somewhere along the way, someone decides to cut corners and gain the system — just a little. It can’t hurt, right? They let someone who isn’t quite qualified in. That person gets a leg up and lets another person who isn’t quite qualified in. And soon enough, the place becomes a group of sub-par people who form a pact to keep each other’s secrets.

That’s corruption. And spending your time and energy isn’t worth it if you want grow as a person.

These places usually don’t allow you to build yourself up with determination and hard work. The company’s blueprint is all messed up, from amendments made by people who don’t know what the hell they’re doing. So no one really knows how to get to success. They only know how to feign it.

I mean, you could just join the gang. But I don’t recommend that.

What you need is a place that values your work and effort. A company that is built on talent and knowledge — real talent and knowledge.

Maybe that’s a no-name company. Probably the dress code will be, just casual. But you’ll likely have real mentors, ones who care and actually teach. Maybe you’ll make good friends — you know, the kind that don’t flex on their designer clothes and fancy cars.

And that’s the battle you want to pick. So pack your things, take your boots somewhere else.

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Jayla Sun

Written by

Jayla Sun

Life is a sea-saw, we’re all just trying to find our centre.

Age of Awareness

Stories providing creative, innovative, and sustainable changes to the education system

Jayla Sun

Written by

Jayla Sun

Life is a sea-saw, we’re all just trying to find our centre.

Age of Awareness

Stories providing creative, innovative, and sustainable changes to the education system

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