Many people have different entry points into Entrepreneurship. To date, there have been countless stories told of layoffs and personal passions creating fertile ground to build a venture. However, everyone’s career falls in a spectrum and variety of job situations. Among those, there are some people that find themselves in dead-end careers; some that are simply satisfied with their positions; others that are supervised by poor managers; and those that find themselves at a precipice between dissatisfaction and wondering how things could be if they ran the show. What do these people feel at the different points of the spectrum? Are you close to that precipice?

My Story

Coming to this very moment has taken every day of my last 34 years. I have dreamt of becoming an entrepreneur since I can remember. It wasn’t the idea of being my own boss, nor the idea of taking over the world, but a simple notion: wanting freedom to express a certain set of ideas and ideals through business.

To be more concrete, my real path towards aspiring entrepreneurship began when I attended INSEAD for an Executive MBA. After many years of trying to obtain a Masters degree, I was fortunate enough to have the opportunity to attend a program that seemed tailormade for me. It pushed and probed me in just the right way and amount, that had me contemplating the idea of leaving the ‘Paycheck Life’ and moving towards freedom.

In July, I had a session at INSEAD that comprised a Leadership Coach and my Leadership group (5 peers going through coaching together). We sat in the gardens of the Fontainebleau campus and in the shade of a beautiful, sunny day, I was being grilled by my peers and our coach.

“What qualities do you feel you are lacking to become an entrepreneur?”

“So what if you fail? What’s so wrong with failing?”

“Why do you keep thinking you’re inadequate to get the job done?”

The questions kept coming and I didn’t seem to have an answer that satisfied them. I seemed to have a well-articulated and thought-out argument that would hold up rationally, but would crumble and get torn apart by anyone with a slight instinct to question matters more seriously and deeply. Going through that moment helped me shatter the glass box that I had been using to trap myself and hold on to a false sense of insurance.

So where to from here? As with any emotional turmoil, one needs a good plan: A bit of money aside. Some support. Contacts in case things went sour. And an idea or a direction.

A bit of money.

How much is the right amount? The leading fear when venturing on your own is money. If ‘Cash is King’, how long can you reign? The fear of money lasting is usually anchored by our ability to maintain a particular lifestyle, have vacations, a funded pension plan, and ensure a cushioned fall for that rainy day. But what if we thought differently? What if it was more important to have a contingency plan than a massive pile of cash?

I personally don’t think there’s a right answer. In fact, I think that you have to come to an acceptance of the fact that its never enough. Moreover, I tried to reframe my own thinking. How long can I survive? Where? And what is my contingency plan? What are the signs that I will need to activate this plan? And do I have a contingency for the contingency.

Some Support.

What if it really all goes to hell? Or what if you need some help along the way? Support structures are important. Beyond the finances, it’s important that you don’t have stresses that make your mind faulter or splay when it needs to be laser-focused. Are you moving towards the right environment where you’re maximizing your probability of success or are you really taking a dark plunge? Once again, there is probably not a right answer. The key is to be aware and continuously looking for blind spots.

I originally planned to go to California. But not knowing anyone that I could rely on in dire straights, I thought about this more rationally and selected Sri Lanka. My parents live there. I speak the language. We have several strong business and political contacts. The economy is booming. What else would I need for the formula to work?

Contacts in case things went sour.

What is your contingency plan? If you start seeing signs of decay and that your idea isn’t moving in the right direction, what is your backup and how long will it take to materialize. Moreover, if that happens, is the backup plan one in which you are able to lay low, squirrel some capital away and try again? Or would you have to hide out, lick your wounds for several years and fear the precipice again?

In the last 12 months, I worked on redesigning my profile. I came to the realization that my personality preferred advisory through creative solutions over daily operations. The result was a movement into topics such as Leadership, Business Thinking and Design. Departing from this point, I was able to round out my profile to remain marketable with both operational experience and Big Vision thinking. I also refreshed my professional networks to ensure that I didn’t fall off the map with many different hiring managers. Finally, I plan on advising as a side-arm as I do actually enjoy it. There will be periods where I am not able to undertake assignments, but I do believe that my previous and future experiences can continue to bring additional perspectives for the clients I will work with in the future.

An idea or a direction.

Before jumping out of safety, what will you do? What is your project? What are your deliverables? When you quit, you want to ensure that you hit the ground running. That means that you already know what is remaining to work on and that you are pushing with all your strength to get those completed.

In Sri Lanka, the real estate market was booming, but because of economic growth. Things were still done in the same, old ways. Though I have not been in the real estate industry before, I have been closely following technology and how it is disrupting most industries. In Sri Lanka, the proliferation of the internet and it’s use is becoming clear. However, the real estate industry seems disjointed. The idea/direction is to organize the information and resources behind real estate transactions so that the consumers have a one-stop shop for all their real estate needs.

What are your next steps?

What tangible steps do you have to take? Create an operational plan. Why can’t you work on them while you’re still working? Being honest with yourself at this juncture is critical.

I had to be honest with myself. Living in Rome, my post-natal city, but home, made me distracted. Working on the side of my day job, while sidelining my social life was a serious challenge. First step: is to move from Italy to Sri Lanka. The process has been delayed for countless reasons, including my recent aversion to risk. In the past, I was ready to jump at any opportunity, but as I have been building my work experiences, I have been grounding my aspirations to safer bets. What is my tangible plan? In the past months, I have started to speak to my father (and business partner) on how to develop the real estate idea. To be (hopefully) successful, we had to be contrarians. Doing what everyone else is doing is to compete in a market that we will not win in. But to look at the real estate market and provide a completely new solution… that is our way to go.

You may not be right, but you do need a belief or a hypothesis to go by. While you operationalize this belief and run into problems, you have to pivot. Knowing what you are willing to do and the direction you are willing to go in is fundamental to make the right decision in your pivots.

Quitting doesn’t make an entrepreneur. Building a successful, if not, sustainable business does (at least in my books).

Thanks for joining me on this journey. Please leave comments/questions below and I will try to respond to them. I welcome your thoughts and also insights on the blindspots I may have missed.

Stay tuned to hear the challenges up ahead.

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