It’s funny how quickly things can change. In early 2015 I was preparing to leave my job at a software startup to get my MBA. My boss was trying to convince me not to leave, he said an MBA wasn’t worth it and it would never pay off. He even offered me a management position if I stayed at the company.

At the time I was confident in my ability to be successful at any company and quickly climb the corporate ladder. I had started at the company just 2 years earlier in an entry-level position, now I was being offered a management position with a nice salary. I was the best person at the company in my role according to quantifiable metrics. I was one of five people in the whole Client Services organization (around 300 people) to receive an award of excellence my final year at the company– I felt invincible.

Despite my success and potential opportunities at the company, I decided to leave in order to get another accolade in hopes that I could move up faster and make more money quicker.

I finally “made it”

Now that I’m done with my MBA, I can say that I accomplished my objective. I switched to a career in corporate finance, I got the hefty raise I hoped for, and I’m working for a Fortune 50 company, none of which would have been possible without that MBA degree.

In my 2015 brain, I might have thought:

I’ve made it! Now I just need to work my butt off, and in 10-15 years I’ll be making really good money! From there I could either continue to climb the ladder, or go elsewhere and be a CFO or Director of Finance. I might even want to find a partner and start my own company. The world will be my oyster then!

A thought experiment

I invite you to enter into a little thought experiment. Think about your career track, think about who currently has the position you would love to have.

For me, that would be my boss’s boss. He is a senior controller (in the finance world that is a pretty big deal) likely making around $300k a year. He has the fancy car, nice watch, and expensive house. He is truly living the “American Dream.”

But why does it feel like something is missing?


A lot changed on August 21, 2017. I remember this date is because that was the day of the Solar Eclipse. Despite being able to see a partial eclipse in our location, we weren’t in the “path of totality.” I vividly remember hearing my senior controller on the phone with one of his business partners, “Yeah, the eclipse was pretty cool. Hopefully, I’ll be able to go to the path of totality the next time. Hopefully, I can watch it with my grandkids.”

This conversation hit me like a ton of bricks. Here was a man in his mid to late 50s who, by all appearances, had made it. He has the money, prized possessions, title, and power in our corporation, but he lacked the most important thing of all, his freedom.

Not only this but throughout his career, he, like so many others, had neglected his health. When his retirement day finally comes, he likely won’t be physically able to fully enjoy the fruits of his 40-year professional labors.

Sure he can visit grandkids, golf, go to the movies and get the senior discount, but what about the adventure? What about hiking Machu Pichu, backpacking through Europe, visiting and hiking through national parks, surfing, bungee jumping, snorkeling in the great barrier reef, running with the bulls, and cage diving with great white sharks?

My thought experiment did not yield the results I would have hoped for. I didn’t look at this man enviously, hoping to be where he is in 20 years. If you are one who doesn’t fall into the same category as me, consider yourself lucky. I would argue though, that many people THINK they want to be like their boss/ director/ owner/ friend, but in all reality, they may not.

People are great at tricking themselves that “they’ll be happy when…” I thought I would be happy if I could just make $30k a year, then make $50k a year, then make $100k a year…. but it’ll never stop, it’ll never be enough. I actually do feel like I’m a happy person overall, but that has very little to do with the money I make, but rather the life I live, choices I make, and my relationships.

Seeing through the Matrix


In the months leading up to me starting this blog I started to feel like Neo from the Matrix (corny I know, but just roll with it). I started to feel like I was seeing through the “American Dream” just as Morpheus taught Neo to see through Matrix.

Continually making more money so you can buy nicer things, which requires more time at work until you make more money, which allows you to buy even nicer things, and the cycle goes on and on, until you reach “retirement age,” and your “golden years,” then you can finally relax and enjoy the fruits of your labor.

For the first time in my life, it felt like a lie, and I wanted nothing to do with it.


My 2015 brain would have never understood the thoughts I have now. It took several years and several experiences like the one I described above to change my stubborn mind and illuminate an alternate path. Staying on the proverbial hamster wheel to continually upgrade your lifestyle is not what’ll make you happy.

Be like Neo, take the red pill, find out how deep the financial independence rabbit hole goes.

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