Escape the Mundane + Experience the Remarkable

The Scariest Time of My Life: The Story of the Day I Quit My Job

It’s a warm autumn evening in 2008. I’m 22 years old. And I just quit my great job at a Fortune 500 company.

My hands are shaking as I struggle to find my mass transit card amongst a bag of papers and desk momentos.

The line of commuters behind me clearly display their displeasure as I’ve taken a few extra seconds to search for the card in my bag.

I’m at the Quincy station of Chicago’s iconic “L” subway system, surrounded by hundreds of people in suits and business casual garb.

By the time I find the card, swipe it, and go through the turn-style, the line has diverted to the other gates. And rightfully so, had it been the day before, I would have been in a rush too.

But not today.

Today I don’t care about rushing. I don’t mind if it takes 5 seconds longer to find my card. There are no signs of any trains coming, so no one is missing anything.

Standing on the platform, I watch them anxiously stare down the tracks for the next train to arrive, as if their focus on the empty third-rail will make the train come quicker.

A few minutes later, the “L” arrives, and the commuters pile into the train-car.

And with no seats available, I struggle to hold onto a handle.

Packed in the car like sardines in a can – and smelling as such – we continue on.

Finally, I take a moment to think back on how I got here:

The Evolution of Becoming an Employee

Having started my first business at the age of 12, I’ve always aspired to become a successful entrepreneur.

But while attending high school and college, the business could never find my full attention. School, friends, sports, and the 5,000 other things that students have going on made it extremely difficult to keep my web design business running full time.

So on occasion, I had also worked part-time jobs while going through school. Which were all fun for a kid like me:

I emulated the shenanigans of Caddyshack at a golf course. I talked computers for 8 hours a day at Best Buy. And I bartended at an upper-class supper club, tuxedo and all… Ask me to make you an Old Fashioned… Best. Drink. Ever.

These were all fun jobs. I gained experience. I earned beer money. But they didn’t mean anything. The jobs were just part-time gigs.

By the time I graduated college though, I had accepted the plight of a full-time corporate job. At least for a few years. Everyone told me a salaried job with good benefits and a 401k at a corporation is the next logical step in post-college life. After all, it is what everyone else is doing!

But the money and freedom I earned from my business during my younger years told me that I mustn’t make this a long-term career path.

And so, eighteen months after graduating college with $70,000 in student loan debt, here I was:

Voluntarily jobless…

Oh shit.

I liked my job. I liked my bosses. I liked most of my coworkers. I liked the money. I liked playing Wii Tennis on the conference room projector. I liked the continuous trainings. I liked the view of the Chicago River from the skyscraper. I liked it all….

But there was no turning back.

What have I done? Why would I give up that security?

Exploring the Employee Mindset

(let’s quickly fast forward to today)

Lately, when I talk with people who are employed for others, the conversation is much different than they are accustomed to thinking about. Because I don’t approach them from the perspective of another employee learning about what they do professionally. But rather, I approach the conversation as a person generally interested by the underlying decisions of their lifestyle choice.

At this point in my life, I generally don’t get why people choose to be employees. I’m rarely empathetic to that lifestyle. So I am always curious about what decisions have led them to their current mindset. And wondering why they choose to forgo their passions for a paycheck.

But over time, I have noticed there are three stages of employee job satisfaction:

Loving a Job

I’ve met a few people over the years who love their job and would never consider doing something different.

While I’ve never understood how someone could love working for someone else, making other people rich, and having to ask permission to do things. I can somewhat see the logic in following a passion while working for someone else.

A full-time writer & photographer for the National Geographic comes to mind as someone who probably loves their job.

Choose a job you love, and you will never have to work a day in your life.
~ Confucious

An extremely talented sales trainer once recited this quote when I asked them why they still worked for their company. And I think about that conversation often. As his thought-process was the first time having a job made sense to me.

Hating a Job

On the other end of the job enjoyment spectrum, is hating a job. This should be obvious for everyone. Hating a job is understandable:

A bad boss, horrible working conditions, annoying coworkers, low pay, boring tasks… the list is endless of why people hate their job.

Hating a job makes it easy for us to call it quits. You often hear of people who get disturbed with their life and make a drastic change. Because change needs to happen.

If you hate something with enough passion, you can find a way to overcome it.

Enduring a Job

I didn’t love my job. But I didn’t hate it either.

Rather, I was ok with it.

And in reality, this is where most people find themselves. They are content with their current job. It pays the bills, it allows for a couple martinis on Fridays, and it offers a decent vacation a couple times a year.

But being content should scare the shit out of anyone.

Because once you find yourself accepting your surroundings, it becomes nearly impossible to change.

“It’s not ideal, but it’s fine,” people say. Subconsciously knowing they are lying to themselves.

In turn, people who are content with the way things are, continue to suffer. Because it’s comfortable and there is no pressing need to change.

Ergo, they unfortunately settle for shitty lives, because it’s comfortable.

Escaping the Confort Zone

(ok, back to the story)

Here I am, standing on the “L” realizing what I just did.

They say ignorance is bliss. And it’s true. Because up until this point, I had only a wild-idea for an Internet company. No real rhyme or reason for leaving my job other than I had amassed the necessary training, capital, and skill-set to start my new business.

I had yet to fully think through the entire scenario:

No more guaranteed income means no more guaranteed life.

Shoulder to shoulder with a dozen strangers, I find myself in an intense fight or flight moment.

What if this new business doesn’t work out? What am I going to do about bills? Where am I going to live? How do I feed myself? What do I do now?

It was fucking scary…

But in those brief, tense moments I fought the urges to crawl back to my job.

Instead, I explored my life’s goals, examined my current lifestyle, and determined why quitting was a good thing:

Because I was confortable with my life.

I was comfortable with the view of the river. I was comfortable with my coworkers. I was comfortable with this shitty commute. I was comfortable with my job.

But I didn’t love any of it. I know my life is destined for more.

So I took a deep breath, smiled, and enjoyed the rest of the “L” ride.

There is no passion to be found playing small – in settling for a life that is less than the one you are capable of living.
~ Nelson Mandela

And now, looking back at that day, quitting my job has made all the difference in my life.

The Uncomfortable Challenge

Writing this post was extremely uncomfortable for me. So I hope you take my experience as a wake up call for change.

I challenge you to take a look at your life from an outside perspective and ask yourself:

Am I truly happy? Do I love what I do?

Or am I comfortable?

But please don’t keep quiet about what you discover. Tell people. Use the comment form below. Facebook your goals with your friends. Tweet your desires to your followers. Email your confidants. Share your desires at dinner with the family.

Do anything that helps you realize how comfortable you are with something in your life. And set out to change it.

Take action. It starts today. It starts now…

Enjoyed this Post & want More?

I've recently launched an online academy where your smartphone, tablet, or laptop becomes the instructor. And your daily life becomes the classroom.

Our courses cover the subjects that matter most to you, everyday life skills. Everything from health & peak performance to money & career development. And each lesson can be completed in less than 10 minutes a day:

Click Here to Change Your Life