Last month, I decided to quit my cushy job and go full-time into building both myself and my array of companies. Most of them have been under wraps for quite a while, as I have been servicing a small number of clients not having the need or motivation to look for more. This was particularly derived from the fact that I had a nice monthly paycheck from my current employer and thus entered into a comfort zone for about a year, and truth be told, it made me sick just thinking of how complacent I had become. So I decided to tender my resignation and risk it all. The psychology behind this was to give me the much needed kick I needed to achieve the goals I had always set for myself and not be complacent. Here’s the thought process that led me down this path :

1. You’re bored

A year and a half ago, I took a job as a Linux System Administrator (without knowing how to use a Linux terminal) after leaving a high-paying job at an Investment Bank. The goal was to sharpen my technology skills while expanding my network and this served as the perfect platform to do so. When I applied for the job, I posted a challenge to the Director of Engineering at that time – Prashant, saying that if I don’t pick up the necessary skills and impress you within a month, fire me. He accepted the challenge and thought I’d make a good culture fit. Within a month, I was confirmed for a full-time position and a few months later he left the company leaving the System Administration to me and the Web Development to Calvin. We survived. The learning curve was great. I had a lot to learn and the job was engaging enough. After a year however, boredom started setting in. The company almost doubled in size and I had to handle the low-level technician stuff and the high-level server administration as well because the job description wasn’t specialized and this resulted in a very very low or almost flatlined learning curve as demonstrated in the pic.

My productivity started waning and my mind was never challenged or excited anymore and it showed. It showed in my performance, and it showed in my motivation. At this point, I started realizing that I was doing a disservice to my employers and what is inherently worst, myself. I had commitments and debts to repay but it was minuscule compared to the brain drain I was in. This was the first and major factor that prompted my decision.


2. You prefer things to go your way

Having worked for both a Regional Investment Bank and a Startup-like Company, and an array of part-time jobs before that in college, I realized that I generally have a tendency of challenging the status quo. I generally tend to like thinking multiple steps ahead and I thank the Operational background I had for that. Its easy to anticipate where the conversation is going and whats the adequate solution for it, but it always puzzled me, why most people can’t seem to do the same. I hate meetings where people mindlessly discuss matters that could be solved by just picking up the phone and calling someone, or just sending an email. I hate meetings where people just ask questions for the sake of asking, and people answer for the sake of answering or what’s inherently worst, they don’t answer at all worried that if they do, they might need to take responsibility for the action items that follow.

I like to run processes and operations my way. I have a system and I like it when people follow it. Of course no process is perfect and I constantly refine my style but that’s how agile a company should be. If you are stuck implementing a process that’s broken and have no way to challenge it or change it, then you’re stuck in what I call “process-hell”. When you see a problem, change it, innovate on it, solve it but don’t ever just sit on it.

3. You have done enough with your portfolio

People always find it hard to believe when I mention what I have done before or am doing now. They find it hard to accept that I could have had such a diverse portfolio at such a young age. They find it hard to believe that I was interviewed for a comment on an article in BusinessWeek during my Junior year in college because of my believes in the democratization of knowledge, and that I got my business-oriented student organization (where I was one of the founding members) in Forbes within a year of taking the helm as President. What you have to realize is people will always be people and what matters is yourself and nothing else. When you have such a diverse portfolio that covers almost all aspects of business, its time to actually implement that knowledge and translate those capabilities towards growing your own companies. I realize that I may not be the best in any of them. Heck, I have a series of mentors in every single aspect of them, some younger and some older than me and significantly more successful than most can imagine, but that’s exactly what motivates me to run my own gig and make things happen.

Most people will only attempt to help or guide you, when they see that you have put in adequate effort in helping yourself achieve your goals. This was the most important factor that motivated my decision. So if and when you’re struggling to decide if you should risk everything and jump into the world of entrepreneurship, ask yourself if you fit some of these criteria ?