In 1987, I found myself in what is called a Junior College (Grade 11) in Mumbai. Within a few months, I realised that many of my classmates, some of my neighbourhood playmates, and many former schoolmates were all talking careers, jobs, applications and the like. This was all Greek to me. Thankfully, I still had my very good childhood friends and made a couple of good new ones and our thoughts on life and living were pretty aligned: let’s learn and enjoy college life and deal with adult-stuff when we get there.

And so, my life went as it had done thus far: study, learn, go to an educational institution (college in that instant), learn, discuss, play, come back home, play, discuss, play some more, and discuss and play some more, go to bed. (eating, etc, is taken for granted). I played soccer, cricket, hockey, ran middle-distance, and played table tennis and badminton. I had started thinking of sports for a longer stint, but hurt my ligaments in an intercollegiate meet. But the learning and play continued.

As a result of this cavalier attitude, soon it was 1989 and the end of Junior College, and I found myself with a mark sheet and a decision to make: General graduation studies, specialist studies? I had no special skills, no inclination to spend 4-5 years in medical or engineering college, and then I found myself sitting for an entrance exam, taking an interview, and lo! I was in India’s best college for Business Management in Hospitality.

And so, my life continued as earlier: study, learn, play, discuss … and work. Work was an addition and it was a welcome one. This was a different college because it taught me to think about business and the running of it and from all possible angles and then some. I was also dancing and started thinking about starting a troupe.

Then, in 1991, I managed to tear my ACL (a knee ligament) asunder, in dramatic fashion. I was undergoing my six-month’s industrial training at the time, snd so, there I was in my crisp, white, chef’s uniform, frying Fish Amritsari in the Searock Sheraton Hotel in Bandra, Mumbai, for the Coffee Shop’s lunch buffet, and my right knee just gave way and I collapsed, literally, on the coffee shop floor. The Resident Manager of the hotel – a tall, well-built gentleman – had to carry me out of the Coffee Shop, the hotel and to the ambulance outside. Surgery followed, blah blah, and so professional sports and dancing seemed out of the question as career choices … but the learning and discussions and play continued unabated.

Too soon, the three years were done. And once again (it was 1992 now), I was faced with an easy choice: Join the marching ants in the hotel industry by going through placements in five-star hotels. All the big and medium and small hotels were there.  Or I could try for one of the cruise liners and see the world. Or I could try for flight purser in one of the new private airlines.

I did the only sensible thing to do under the circumstances: sit at home and watch MTV … for four whole months. I had company, one equally thoughtful friend, Dmess, who also wanted to take in the great education we had received and ponder over why it ought to be used to join a line to climb up a ladder. Any ladder.

Between 1992 and 1996, I worked 9 jobs in 9 different companies (some were more like outfits), I also cooked as freelance chef for catering outfits, helped out (as bartender) classmates who had started their own catering outfits, tried my hand at selling insurance, trained people at service and technical skills (one of the great benefits of an education from an industry-integrated college), and wrote several business plans. I sold stuff, made stuff, managed ice cream parlours, restaurants, pubs, organised events, was a travel guide, sold amusement parks to corporates and educational institutions for their annual picnic, and did sundry other stuff that caught my fancy. Now this was a time when a majority of people were building careers or career paths. Dmess and I on the other hand were floating about. Which meant we were not just frowned up but shunned even as bad influence since it was expected that in mid-20s youngsters would be constructing a career and preparing for a successful future. By the third year of being vagabonds, people started coming to us for opinions, inputs, advise even, but I soon realised that no one really listened. People just wanted to talk about their problems and challenges and to be listened to and told that it would be all right. So, I turned my attention and efforts on the one person who had to listen to me and do what I say if his life had to be better than it was: Me.

I learned a lot, especially about myself and people and what kind of work I liked to do and didn’t like to do, and created many new ideas, collaborated, and practiced, practiced, practiced. Practiced what? Practiced being myself.

I then shifted to Pune, went back to college, and became a journalist for three quarters of a decade (the first job lasted four months which was pretty much my benchmark, the second one lasted more than six years, much to everyone’s surprise); later shifted to the nascent learning industry for another half a decade, and all along the way, I kept learning, till one day I was ready to answer the questions I had consciously set out to answer since leaving college: Who Am I? What is my place in the world? How do I related to all that is around me? Did I want to be an employee or an artist or a self-employed person?

In essence, there is very little difference between being an employee, an artist and an entrepreneur, if one enjoys the work they do. The contrary is also true: there is very little difference between being an employee, an artist and an entrepreneur, if one does not enjoy the work they do. The difference lies in how the value of your work is perceived and who takes how much of that value. I am deliberately identifying ‘artist’ as a separate category of work approach and the reason for that will be a different rant.

But getting back to 2008, I looked at my work trail and found that I had enjoyed all the work I had done and learned and become proficient at. Whenever I had stopped enjoying something, I had stopped doing it. And in that moment, I quit yet another job, and revived a Social Enterprise business plan (the last plan I had written for myself ten years ago), because I was now crystal clear about how I wanted to do it. And so, I became a self-employed consultant.

I was 37 at that time, married with an infant in arms. At heart and by core skill, I continued to be a writer, composer, and artist. And that’s how I see myself: A person of many trades, who is self-employed. I am not a business person or an entrepreneur. I am not an employee or an employer. I am neither a servant nor an owner. I am just me.

I have three little children now, and I work as hard or as little and play as hard or as little as I ever have. I have two very small start-ups, one long-term consulting client, two short-term consulting engagements (different industries), minority equity interests in a couple of artistic endeavours, and a collaboration team of 13 highly competent and passionate professionals from very diverse backgrounds. I have an ever expanding circle of friends, family, well-wishers, acquaintances and strangers who I work with, am helped by, collaborate with. Every day is as hard and as tough as it can be, and every day has moments of joy, pain, toil, frustration, exasperation, satisfaction … and I am grateful for it all.

My best friends are mostly employees (except for one artist, and one entrepreneur), and all are in different professions. All of them except one have been in the same industry (a couple in the same company) for more than two decades. Exactly opposite of the way I have plodded along. And they are all as engaged, occupied and passionate about their life as I am.

So what should one be, and when should one take the decision?

You know what? There is no right time for doing anything. And there is no wrong time for doing anything either. Whenever you do what you do, is the right time. Some times things won’t work out; you can try again at a later point in time when you are better at doing it or conditions are more conducive. Some times things will work out; you can make it better by keeping at it; or you can do something different, learning some new lessons, applying old ones. It’s all in your hands. There is no judge or jury on what makes you, you and what makes your life meaningful or not meaningful.

In essence: There Is No Box.