My Dead End Job: How I Became Self Employed (Part 1)


When I graduated college, I was beyond excited to start my career. I had succeeded in the academic world – earning both good grades and various extracurricular awards – and thought the same principles would net similar adulations in my career. But little did I know my first year in the “real world” would transform my dream gig into a dead end job.

Shattered Expectations

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”

Nassim Nicholas Taleb

I was wooed into accepting my first position by bold promises from a charismatic executive – one that would unexpectedly announced their departure during my third week on the job. The innovative project I eagerly looked forward to joining was left without a champion and ultimately faced a slow and painful death. 

I quickly learned that very little was in my control as an entry-level employee at a massive corporation. 

Soon, my team forgot about me. My half-hearted, passive attempts to find more intriguing projects fell short. Soon, I was left spending my days looking busy instead of being busy.

Friends mocked my frustrations. They wished they could spend their days on Reddit or Facebook instead of suffering through the gruesome boredom their jobs shackled them to. But for an ambitious person, nothing was more depressing than a dead end job.

The van I lived in during this period…out of boredom more than anything

Hours passed slowly. Days were a blur. Weeks and months flew by. An emotional and mental fog tortured me. 

I started showing up later and later, but left earlier and earlier. I gained thirty pounds because eating refined carbohydrates and fatty foods was the only thing that genuinely brought excitement to my day. And smoking weed daily was the only way I found to escape my reality.

This slump lasted for months. But as my vesting date approached, I felt hopeful again. I started taking action to change my situation.

How to Leave a Dead End Job

“Happiness is not something ready made. It comes from your own actions.”

Dalai Lama XIV

I began applying for jobs that fit my interests. The only problem: I had no tangible skills or accomplishments in my current job. People think I’m embellishing when I say I made six-figures doing nothing for over a year…I wish I was joking. 

With no concrete proof to back up my marketable traits, I found it hard to get interviews or offers for the competitive jobs I constantly applied for. My resume seemed to fall into a black hole.

Tired of the helplessness and rejection, I started taking action. I knew that working on committees and projects outside of the classroom helped differentiate my resume when I was in college, so I applied the same framework to my after-hours projects.

I stumbled upon a book called Recession Proof Graduate by Charlie Hoehn which changed my perspective on landing jobs. Instead of being reactionary and applying to job listings, there’s a massive opportunity for those who are proactive and lead with value. 

The email I sent to land my first freelancing client

I used Hoehn’s tactics to land some freelance projects for businesses I was passionate about. Because I had experience launching my own blog, online store, and side hustles in the past, I built a small foundation of online content marketing knowledge. I knew I could provide value to smaller businesses that may not have the experience I did.

I looked for companies that were doing things I admired, analyzed their current digital presence, and came up with ideas for them to improve their operations. Using the templates laid out in the book, I sent cold emails and was chatting with founders soon thereafter.

My Introduction to Freelancing

“Try not to become a man of success. Rather become a man of value.”

Albert Einstein

Since I was a kid, my dream has always been to be the GM of the Indianapolis Colts and lead them to multiple Super Bowls. While that goal has since evolved slightly, my love for football remains. I know the game will play an important role in the rest of my life, it just won’t come in the form of a career.

But, at this point in time, my obsession was landing a job working for an NFL team. I didn’t care what it took, I was willing to put in the work to make it happen. Using the aforementioned strategy, I started gaining experience in the sports world. 

I freelanced for a startup focused on supplying American football equipment (helmets, shoulder pads, etc) to European teams. That helped me land a gig as a contributor for a fast-growing sports-business blog. I did the hard work necessary to build experience in a competitive industry. 

An awesome interview I landed through free work

And while I rarely made any money from this freelancing work, I learned the power of leading with value. Both clients gave me access to events (e.g., the NFL international series, LA Dodgers Accelerator demo day, etc) and people I couldn’t have reached on my own. I built momentum and started to understand that I could control my own destiny. 

After a few months of grinding out articles and optimizing WordPress sites, I figured I had enough experience to stand out in the crowded sports marketplace. I figured that, with my engineering degree, “prestigious” corporate dead end job, and extra freelancing work, teams would be champing at the bit to interview me.

But I was in for another rude awakening.

One Comment

  1. Justice

    Thanks for sharing this. I think it’s crazy you were making $100k for your first job but totally get being so frustrated by a dead end job. I’ve also had a couple jobs where things were not as advertised soon after. One was thankfully salvaged but one was extremely terrible

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