Start with “Why?”

Stanley Chia
4 min readNov 25, 2020

“Why did you choose entrepreneurship as a career?”

This was the question I’ve been asked the most during the initial phase of my entrepreneurship journey, and one which I took almost a decade to answer. It is a difficult question that I believe every individual regardless of age and seeking the path of entrepreneurship would have to answer.

Yet, for every entrepreneur, their answer would be different. It is often a unique, deeply personal, and self-reflective answer that you would have to find for yourself.

You can be inspired, you may seek advice, but the conviction required to fuel your perseverance through the ups and downs you will soon experience, needs to come from within you.

One of the most impactful videos that inspired me to seek the answer to this lofty “Why” question, was none other than Simon Sinek’s Ted talk on “How great leaders inspire action?” In his speech, Simon explained that in the core of all things we do, what matters and inspires people to follow, are often not what you do or how you do things, but the “Why?”

The “Why” lays the foundation for your purpose and motivations behind your actions, decisions, or cause. Before you attempt to sell your grand dreams/plans/ideas/vision to others, you have to first be able to convince yourself and the clearer it gets for yourself, the more aligned your actions and decisions would be. Derek Sivers nicely put it, it would be your compass that guides you and allow you to optimize towards your goals, especially when you are lost or in the slums.

Reflecting on my personal journey and stories of the past, I realized that my search for answers surprisingly began in my secondary school days. Though I may have failed in school, these failures brought me the opportunities to seek my own definition and path of success. The unceasing internal debates eventually led me to ask myself the question of…

Which career will allow me the path to achieving my personal definition of success in life?

Running down the list of aspirations, it came down to the realization that I needed to take charge of my own life, my own destiny. Instead of living in the paradigms of what society defines as success; in school, we use grades, post-school we use salaries when we’ve achieved financial success we seek other more profound ways to find meaning in life.

The goal post is an ever-moving one. Since our destiny is different from each other, why do we let society define us? It should be ourselves that decide who we are, can be, and should be.

And the only career that will allow me to do this, would be to become an entrepreneur. Entrepreneurship is not only a career, it is a lifestyle choice, a decision to take charge of your destiny, to define your own rules. As the “Boss” you make the decisions. You are accountable for your own decisions, and one of the perks is that you get to hire and work with those who are brighter and more talented than you.

Nonetheless, being the Boss isn’t the easiest job. In fact, I soon receive a hard surprise at how hard it would be. Just as Christ, who washed the feet of his disciples. I believe the best example of what a leader should look like can be seen in the Bible. As a servant leader, you will be the last to eat, the first to wake up, and at times of failure you take all the blame. Nonetheless, on the flip-side, if you can attain the respect and loyalty of your followers, the accumulated competencies, resources, and personal aspirations of everyone within your team can be aligned to help you succeed in achieving yours. And just like how the first-comer of any race is the one and only one, who is given the greatest recognition, so too will you be the one who receives the greatest rewards. Not always monetarily, but most definitely the realization of your dream. A destiny defined by you, led by you, owned by you (Not others).

So whenever a young aspiring entrepreneur asks me for advice on what he should do about his brilliant business idea, my first answer will always be “Just do it!” or when I’m overly passionate, “Just F*&King DO it!”

With all that has been said, it is crucial for anyone pondering on diving into the world of entrepreneurship to be brutally honest with oneself with the simple question of “Why?”

If you want a simpler life from your meaningless routine at work, it can perhaps be easier to just change your job.

If you want to enjoy riches that you can never imagine, then you may want to be reminded that there is only a statistical probability of 10% for you to succeed in your enterprise.

If you only desire recognition and have people clap for you, then you ought to consider a career as a clown or a comedian.

According to Derek Siver’s advice, it may be perfectly fine if one or more of the above reasons is what you truly desire. However, personally, I encourage you to seek a higher-purpose and values-driven approach before taking the plunge into the life of an entrepreneur.

Your hunger for success must be fuelled by more than just fame and/or fortune, fame and/or fortune are lower ranked in Maslow’s Hierarchy of Needs, which means that these short-termed needs can be easily fulfilled. Once achieved, then what’s next? Therefore, I implore that even if your initial motivations are of such, continue to challenge yourself to seek a deeper and higher purpose. Be genuine in your quest to create value and make a difference in the lives of others.

Use your powers and brilliance for good.

I pray that this personal reflection would be of value in your personal journey in answering your “Why?”

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Stanley Chia

Stanley Chia is the Co-founder of Cialfo, an edutech startup on the mission to democratize college access internationally.