Chasing Unhappiness

While lazing around on a Sunday afternoon, my mind, like most entrepreneurs, was working. In doing so, I asked myself one question – The day you reach the heights of success you’ve always envisioned for your company (my BHAG – Big Hairy Audacious Goal), how will you feel that day? The answer surprised me – Emptiness.

While I would feel a strong sense of accomplishment, proud of our team and what we built together, I also became acutely aware that it would be a shallow experience; I would feel a deep sense of emptiness.

With no credentials in the field, I started and ran a successful technology company with my brother. We worked with incredible clients like Samsonite, Taylor Swift, Pokémon, Viacom, Red Bull … the list was endlessly impressive and worthy of giving anyone a hard-on for days. The journey was not easy; and against all odds, we had accomplished something pretty cool. There was so much to be proud of. So why would anyone feel empty?

Working hard and with passion is part of my DNA. That will never change. But why was I driven to work so hard? After digging deep and cutting through layers, I discovered that I wanted my Dad to be proud of me. This came as yet another surprise since my Dad has always been proud and supportive of me. It’s amazing what you can find in the subliminal recesses of your being!

In business, we quickly learn that everything needs to be measured. So the only way I knew how to measure “success” in a quantifiable way, and hence, have my Dad be proud of me, was by how much money was in my bank account. While this was the primary driving factor, with all honesty, there were other reasons that were more self absorbing - personal ego, status and desire to leave a legacy.

I was chasing unhappiness.

And with that big aha and punchy insight, I took a revolutionary step the next day – I went back to work like every other day! And the next day, and the next, until I was able to drown out that insight by the noise of the daily grind. Sound familiar?

We find comfort in familiarity, stability and routine. It’s predictable. No matter how miserable we may be in our careers or personal relationships, we go back to what we know. Such choices have striking similarities to how domestic violence victims keep going back to their abusers.

Our decisions are driven by two things - our desire to seek pleasure and avoid pain. So we choose the seemingly “easy way” out. The alternative is hard and even sadistic. It requires us to dig deep and be brutally honest with ourselves, and others. And during this soul-searching journey, we could be lost for months or even years. That’s uncomfortable and painful.

Like everyone else, I did that for a while. When we accept mediocrity, resign or fail to have the courage to discover and live our purpose, it’s the fastest way to sentence our soul to a slow death. This is the moment when we cease to live, and choose to exist. We become the judge, jury and executioner for ourselves.

So what is success anyway? Society teaches us that “success” is money, power, status, fame, fancy titles, an office with a big window on the 18th floor, climbing the corporate ladder, hobnobbing with the big wigs, owning expensive things, having a custom home in an exclusive location, making it on the cover of a magazine, having thousands of followers on social media…

If any of this were true, then why would I feel emptiness the day I would reach the pinnacle of my “success?”

When you chase the wrong things,
you outrun the right things.


Success is none of the things that society has taught us since childhood. Knowingly or unknowingly, we choose to buy into society’s definition and system, without questioning it. So we dedicate our entire lives to chasing the wrong things and then wonder why we are unfulfilled or miserable.

None of what I’ve shared so far are earth-shatteringly new revelations. It’s fairly common knowledge that success is none of those things. The key, however, lies in what we choose to do with the knowledge and awareness. Do we choose to do something or nothing? Do we choose to think or do we choose to convert those thoughts into action? Where most of us get stuck is in the implementation and execution phase. That requires courage, perseverance and enduring some painful times on roads less traveled.

The realization of emptiness, along with being in the throes of depression from life events, allowed me to question my definition of “success” through the right lenses. Ironically, in such trying times, you have clarity and really understand what matters in life. And just like that, the moment I changed my definition of success, my entire life twisted around!

After several renditions, I re-wrote what success means to me. This is where I am today – “Success is sharing love and happiness in abundance.”

There are certainly more conversations to be had regarding this new definition. But amuse me for now … If this is the new definition of success, then what does happiness mean to you? How would you change your life and execute on this new finding?

Photo Credit - Michael Luna Photography

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