What I learned From ‘Retiring’ Early, and Why Entrepreneurs Should Never Retire


When I was 18 years old, I was stuck with this idea that I would retire by 30. I think we all in some way, shape, or form, share a desire to be retired earlier than the average 70 year old person. At the end of the day, what is the point of retiring at an age where you can function in your optimum stage? None, if you ask me which is why I was always fascinated by that idea early on. By 18, I was determined to find way regardless that it was through owning a business, investing, or even having a career.

I reached that goal but it looked very different than what I originally envisioned. I guess what really changed wasn’t the vision but rather my definition of the word retirement. When I was 18, I envisioned retirement as not doing anything, sitting back, and simply enjoying life. A life full of adventures as most of us desire, free of any worries about money, or having to report to anyone. My definition today is drastically different and focused on fulfillment and impact, rather than a lavish and playful lifestyle.

I did reach my goal but as you’ll see by the end of this article, my view on retirement is very different today as it once was. Based on my experience, I assume the majority of the working class who is ambitious and driven will go through a similar transformation and process.

I retired from Corporate America at 25. After a 6 year career moving up through the ranks and truly pushing myself to new heights of learning, I managed to do tremendously well in real estate allowing me the financial freedom to no longer depend on a  job.

When Corporate America gave me the boot, it only made sense that I no longer believe in it, therefore chose to focus my efforts on small business ownership. I can say that without a plan to make money while I was being a banker, I would have never retired from it.

I learned early on that you can never retire wealthy from Corporate America unless you are ok with being old when doing it. My ambition to retire by 30 was met by my understanding that an alternative way was needed even though I enjoyed my work as a banker.

I then found myself faced with the constant pursuit of the next level of financial freedom. The one that includes making 7 figures working for yourself on a yearly basis.

Working 3 years back to back, I found such freedom with VIP Motoring which quickly became a great business to be in, but also helped me reach a whole new level of thinking, making me realize that I once more needed a transition.

Except this time it was on my terms and things were quite different as it wasn’t so much the pursuit for more money or further freedom, but rather legacy. My second retirement was from small business ownership and it came without an exit from business. It was rather an opportunity to trade money for time by hiring a general manager to run my business instead.

My last transition was that of a business owner gone entrepreneur and while it was very difficult, it was my best transition yet. While business ownership and Corporate America were much more rewarding from a monetary basis, they certainly didn’t seem to ever have an end, as the pursuit of profits seem to be never ending.

In entrepreneurship, I found something much more valuable than money and something that I felt could fulfill the word legacy rather than retirement. While my other businesses fulfilled my monetary ambitions, none ever would be creating a legacy for myself and therefore while they allow me to retire from money, they would ultimately only be a graduation past the second circle rather than the third circle, which is the only on that matters in life.

You see, I learned after my first time retiring from Corporate America that no matter how hard you work, how much time you devote to your work or how successful you are chasing money, no one will ever care as you are simply an placation away from being replaced. You are only part of a machine, and it is the machine itself or the creator that is remembered, rather than the very small pieces that keep that machine lubricated.

In entrepreneurship, you directly impact others based on creating value or facilitating a way of life and even when you own a business, it is very unlikely that you reach such heights of fulfillment.

This is why entrepreneurship is so much more than just creating things to sell them, it is truly the place where a person takes on a new crossroad in their life and makes a commitment to reach new heights in life, which is why such commitment can never be tied to a retirement simply justified by money. This is why many entrepreneurs can never truly retire.