I Just Quit My Job. Here's What was Holding Me Back.

Last week, I left the job I’ve had since the moment I left college. To many, this wasn’t a surprise. I’ve always expressed my desire to be an entrepreneur and to “do my own thing.” I’ve talked a big game for years, always having some sort of “big idea” I was working on. First it was a recording studio, then it was a social media app, then it was Leavit, then my podcast Philly Who?. When asked about each venture, I would beam with passion and dive into some sort of tangent about how much I loved doing it. Then, in a way that felt almost apologetic, I would add that I’d be working on it in my spare time, since I had a day job.

My former coworkers were nothing but supportive. They even got me this cake from  Cake Life !

My former coworkers were nothing but supportive. They even got me this cake from Cake Life!

It wasn’t that I didn’t like my place of employment. Cigna really has a great company culture, and tons of opportunity to learn and advance your career - if a corporate career is what you want. It took me a while to admit that it isn't what I want. When I took the job out of college, I thought that the goal was to get a great, stable job with a high salary. Through Cigna, I won that game. Crushed it, in fact. Yet… I still had a constant yearning for something different.

For a long time, I felt bad about this. I was making more money than most people I knew right out of school. I got several raises, traveled a ton, and bought a house when I was 23. Who was I to be so unhappy while being so fortunate? It ate at me for ages, as I continued to dread the alarm clock in the morning. The stuff I was doing 9 to 5 was interesting enough, but it didn’t excite me. And when I would get home, there simply was no mental energy left for the things I really wanted to create.

I thought that I had missed the boat on entrepreneurship - with a car payment, mortgage, dog, and student loans, I had become a slave to the things that the job afforded me in the first place. 

Then, in August 2017, a book changed my life.

I always thought it was super cheesy when anybody said that a book changed their life. How can something change your perspective so dramatically? How can an idea that alters your reality be so hidden in plain sight? Can a book really give you something life-changing that you never have considered before?

It turns out: no. At least, not yet for me. But what a book can do is tweak your perspective ever so much, so that it opens new doors to brand new ideas and newfound confidence.

For me, that book was The 4-Hour Workweek by Tim Ferriss. Granted: the title is a little gimmicky, and he can be a little pushy in the book. To be clear, the book is not about only working 4 hours a week. The essence of the book is this:

The way we spend our time is often inefficient and unproductive, and sometimes you have to free yourself of the arbitrary 9-to-5 grind in order to live the life you want to live. 

Bingo. What I didn’t understand for so long is that the discomfort I had with my cushy job wasn’t me being ungrateful, it was my inner self rejecting a reality that had been prescribed to me by society.

Society tells us that the goal is to get a job.

Why do you go to college? “To get a good job.”

How is our economy doing? “Well, how many people have jobs?”

What’s the worst thing that could happen to you? “I lose my JOB!”

Who cares? Why is our metric of happiness based upon whether you sell 40 hours of your time per week to somebody else?

I’m not here to answer that question, though it probably is residue from the industrial age. Back then, the 40-hour workweek was arbitrarily agreed upon and then unilaterally applied to every singe industry, regardless of whether or not it made sense.

I am here, though, to answer the two questions I’ve been asked by each person who has heard the news. The first one:

“So what are you going to do now?”

Remember all of those things I did before in my spare time? Music Production, Software Development, Developing Leavit, and Podcasting. The answer is: all of them!

My plan is to simply make a living doing the things I want to do with my time. 

Now, before I continue gushing about how I’m throwing away a life that many yearn for, let me check the privileges I have: I have natural societal privilege in that I’m a straight tall white male. I have a natural disposition to enjoy creating things that people want to buy, and I have natural talents in music, productivity, and creativity. I have also acquired the privilege of financial runway through 4 years of a very comfortable salary. Finally, with no children, no significant other, and only moderate financial debts, I have little responsibility. Given all that: I have to make this move. I’m so fortunate to be in the spot that I am, why wouldn’t I take the chance to live my dream?

I firmly believe that through making my own music, DJing, freelance software development, launching Leavit, and the continued success of Philly Who?, I’ll continue living a comfortable and exciting life.

And while I don’t have a ton of revenue pouring in yet from these other ventures, this plan of mine to go out on my own was concocted back in August when I first read 4HWW. I was on a flight to visit a friend in Boston, and in that 90 minutes, I devoured the whole book. As the plane touched down in Logan, I made a vow that come next April (8 months), I would be in a place to take the leap. I would bet on myself for once, and adopt a life of excitement, creativity, and travel.

April came, and for various reasons I decided it would be best to wait until mid-June. But, the deadline had served its purpose: I was ready. I’d managed to shrink my expenses: I sold my car in February. I consolidated my “office” into my bedroom, and picked up a third housemate. I’ve reduced my food, drink, and entertainment expenditure dramatically. With a few months’ cash in the bank, it was time. 

It’s now July, and I’m writing this blog post from a hostel in Paris. 

The second question I’m asked:

“Are You Excited?”

Of course I’m excited! 

I’m also absolutely terrified. I’ve actually never been existentially scared like this before. At this moment, I have a finite bed of savings, and definitely not enough revenue to meet my monthly spending. So, there’s an expiration date to this arrangement. I’m over 26, so I’m gonna have to figure out Healthcare (ironic, given I just left a major health insurance company). I have student loans, a dog, and a mortgage - none of those things are going away any time soon.

But, for the first time since - well, ever - I’m excited when the alarm goes off in the morning. I get up, jump into whatever it is I’m creating, and suddenly it’s 10pm. It’s invigorating.

I have confidence that by the end of this year, I’ll be back to making what I’m spending. And, if I’m wrong, I’ll get by for a while. I'll DJ some weddings, build some websites, whatever. But I’ll get there.

Oh, actually, there’s one thing that everybody says before asking those two questions:


Congratulations? I just tossed away financial security, disposable income, and an extremely respectable and lucrative career. I’m now jobless. I’m a statistic that says the economy is doing badly.

I thought that society was to blame for pressuring me into the path of least resistance! Why are they celebrating my escape?

Nonetheless, every single person has congratulated me. When I ask them why, they say its for taking a risk and believing in myself. Some then say that they wish they could do the same.

So that's what was pushing me into a life I didn't want. It wasn't society. That simply was an excuse to avoid the truth:

It was fear.

When I tell my congratulators that they too can take the leap, they laugh.

“Oh no, not me.”

Maybe so. There’s nothing wrong with loving your career; many of my friends do, and that’s admirable.

Or maybe you do have enough responsibility to outweigh the risk.

Or, you don’t have the financial leeway I have accrued.

I’m a lucky guy, to be sure.

Just don’t kid yourself. If you aren’t happy with what you’re doing, take a hard look at it. Read The 4-Hour Workweek, understand its underlying principles, and know that those principles can apply to any job, career, or life. 

If you have any doubts, think long and hard about how and to whom you’re selling your time. If you work 40 hours a week, 70% of your waking moments are sold to somebody else in exchange for cash. And we’re taught to be grateful for the chance to sell that time to them. They’re not doing us a favor; it’s a business exchange.

If you’re like I was, and you’re making that sale every day solely due to fear, or others’ expectations, maybe it’s time to consider an alternative. Does that daily transaction make sense? Is it the best return for your time, attention, and energy?

This may end horribly for me. But, if I hit the floor, I’ll be alright - I can get another job. I’m incredibly grateful that I’m in a position to take this opportunity, and I also know it’ll be singlehandedly the hardest thing I’ve ever done in my life. I may fail and wind up back in the 9-to-5 life, but at least I’ll know I gave it the best I could. And, I could always try again. 

In the meanwhile, I ask you this: take a hard look at the decisions you make every day, and ask yourself whether you’re acting out of fear and obligation or out of excitement and curiosity.  At this point, you probably already know the answer to that question.

Either way, whether or not you change a thing, you’ll have thought critically and for yourself. You’ll have taken the first steps towards fulfillment and owning your fate.

Now THAT is what deserves congratulations.