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Why Plans Are Overrated in My Life

And How I learned to Trust Serendipity More

“No operation extends with any certainty beyond the first encounter with the main body of the enemy.” — Helmuth Von Moltke

The pithier version of the above quote is “No plan survives the contact with the enemy.”

This is not to dilute the value of plans or the process of planning. Both are important. However, over the years, I have realized that plans are overrated in my life and slowly and steadily I started placing more trust in serendipity.

Here are few of the incidents (partial list) that influenced me to make the switch.

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8 years old

#1. The Library

My Dad used to work in Public Works Department (PWD) and we used to live in a small town called K.R. Nagar. One day my Dad came back home and told us that he has been transferred to Madikeri and we all will be moving.

It was quite common for us to move every few years as that was the nature of his job. But Madikeri? I did not even where it was. He told me that it only rains twice there in a week — first time it lasts four days and the second time it lasts the other three days. I love rain so I could only imagine how the place was going to be.

We didn’t know a single soul in Madikeri but soon I made some lifelong friends from there. When your Dad has a traveling job, a lot of things are not under your control. However, the very same fact opens up new avenues for serendipity in action.

What made the difference in Madikeri?

Of the many things, one was the location of the library and how far it was from our home. The library was located in the Madikeri Fort and we used to live in PWD quarters right outside the town. It was about 4 kilometers from my home if I am not mistaken. I used to walk almost every weekend to the library. While walking back home I would read one of those books on the road and if I completed reading it, I would walk back to the library to return that book and exchange for another one. Soon I discovered that it would be better to borrow thicker books so that I don’t run out of reading material.

If it were raining, that would provide an excuse for me to spend hours at the library reading books right there before heading home with two more.

Long story short, the reading non-stop for years finally led to me writing my own book at the age of ten and finally getting it published at the age of thirteen.

Plans, No. Why? Didn’t know what it meant at that age.

Serendipity. Yes, a series of events in that category is what made it happen.

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14 Years Old

2. The Hindi Exam AND The Big Lesson

By this time, I had published my first book and had written several hundred articles and poems. One of my books was about to be serialized in a monthly magazine. I used to get fan mail from people. That was one side of the story.

Then something interesting happened when I was in Eighth Grade. A teacher by the name of Govardhan came into the class to teach Hindi language. He established his authority and credibility right on day one in the way he approached his very first class. I still remember the first day. He threw his textbook to one of the students in the first bench and asked the student to randomly open the text book without showing the teacher and read out a line of a paragraph. Govardhan Sir would immediately say what chapter, page number, paragraph number and line number within the paragraph that line belonged to. First, I thought it was a setup. Then the exercise continued. The textbook was passed from one student to the other and the result was the same. Govardhan Sir would remember the chapter, page, paragraph and the line number for any sentence in the book. When the book was passed to me, I wanted to test this some more. I opened a random page and instead of reading something from there, I made up a sentence and looked at the teacher. Govardhan Sir was not happy. His response, “CP, don’t play games with me.” Then he spoke a sentence that was on the first line of the page I had opened. I was on the last bench. Govardhan Sir had guessed the exact page based on what he saw from the front. I was shocked, surprised, amazed and dumbstruck all at once. The power of the mind fascinated me.

On the other end, my parents were very clear that I had to keep getting good grades in school or else everything else outside the studies would come to a grinding halt. In hindsight, it was a good thing because I found ways of managing what was required for my studies in a very efficient way. Planning? No. Again, I didn’t know what they really meant at that time. I was doing what was necessary. That led to my interest in accelerated learning, music to enhance learning and so many other techniques that I use even today.

There was a Hindi exam called “Pahali.” Inspiration from Govardhan Sir and all the learning I did via my other research helped a ton. I surprised myself by securing 1st Rank for the State.

More than anything, Govardhan Sir taught me about expanding the possibilities simply by shedding our limitations and constraints.

Planning. No? Inspiration and Serendipity — A big Yes!

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16 Years Old

We used to live in Hassan during my Class X. By this time I had published several books and I was written up in magazines and newspapers for my ability to write fiction. However, the litmus test for students in India is how they fare in Public Exams. There was a lot of pressure to perform well and to prove that my talents were not simply limited to writing fiction and early journalism. My parents worry is that it may be difficult to put the food on the table with literary accomplishments however cool they were. In a way, I agreed with them and better yet, I didn’t have a way to prove them otherwise.

However, being one of the Top 20 among 460,000 students who were taking exams that year was a big stretch. The school that I was studying at Hassan didn’t have any history of anyone getting a state rank. The odds were clearly against me. It was a remote chance at best.

The preparation was good, exams were over and the results were announced. The first twenty ranks were usually announced in all major newspapers. It would be too optimistic to think I secured a rank, but that didn’t stop me from checking the morning newspaper. I quickly scanned through the entire list and did not find my name. I was disappointed but there was nothing I could now. My family members might also have scanned the newspaper and having found nothing, they didn’t say a word. There was more silence in the house than normal. Probably they didn’t want to add to my disappointment.

Around 10am, I got ready and started walking towards my school to get my scores. It was a 20 minute walk. Along the way, any known person who met me congratulated me. At least six of them. I thought they were congratulating me. I thanked them all thinking they were congratulating me because I had passed the exam.

Only when I reached the school did I know that I had secured 20th Rank for the state. They were celebrating at the school. I had checked the newspapers and wondered why I didn’t find my name. The answer was simple — 20th Rank like many other ranks were shared by THREE students and my name was in the middle. I had totally forgotten about the possibility that ranks could be shared.

In that moment, my life took a completely different turn for the positive. Until then, I had not thought of what college to join. But suddenly, everyone around us started advising all the best colleges in the State as possible options. After much debate, we finalized on National College in Bangalore and I would stay at the Ramakrishna Ashram hostel close by. At least that was the plan.

Per our plan, we went to National College next week. Little did we know that the seats were all filled up several weeks ago. It seems like an obvious thing now as that was one of the best colleges in the State. It didn’t matter that I was one of the Top 20 in the state. They refused to give me a seat.

With great disappointment, we returned back. On the way to our village, we stopped at Tumkur. My cousin Srinivas listened to the story and asked me why don’t you join the Sarvodaya College in Tumkur. That was the college where Srinivas had studied — in fact, he was the student of the very first batch of Sarvodaya College. He had some influence there.

Long story short — I ended up joining Sarvodaya College — happens to be one of the best things to happen in my life for many reasons. Read about The Final Push here.

Planned? Nope. Serendipity — Oh, Yes!

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22 Years Old

4. Joining CITIL

I passed my Electronics Engineering course with flying colors securing 4th Rank for the University. Two of my close friends and I decided to start a company as soon as we got out of the college. It was going to be a training institute that we would start in Mangalore. Won’t go into the details but it was a mini disaster. This meant I would have to find a job. I had to do that quickly.

My Brother told me that Infosys was hiring and I could take the placement test. I wanted to give it a shot and took the placement test. I don’t remember what all the test covered but I did reasonably well and I thought the next step would be the interview. I was wrong. There would be another filtering test and only those that pass that test would be offered an interview. I was game for it. Or, I thought I was.

The second test had only six questions. But they were all like brain teasers. We had one hour. I am not good at these brain teaser IQ puzzles. So I had to work really hard. I was able to complete four of them and I was almost done with the fifth one when the bell rang. I had to give back the paper without actually completing solving ALL the problems. It was over with Infosys. There was no point in waiting for the results as there were literally hundreds of people who had completed all of the questions. Many of them had completed those questions in less than 45 minutes. Unfortunately, I was not one of them.

I went back home and started getting good at solving these IQ problems.

Next week, my brother alerted me about another opportunity with a company called CITIL (Citicorp Information Technology Industries Limited). This time I was super prepared and didn’t want a repeat performance from the Infosys test. It was a similar series of tests but being prepared helped a lot. There were about 1,000 people who took the test and 20 of us finally made the cut and joined the company. Of all the companies I have worked for CITIL stands out the best. People were super friendly. My batch mates were awesome AND the learning was phenomenal. It was like one big family outside of real family.

Planned? No. Serendipity? You bet!

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5. Coming to Silicon Valley

After a 2-year stint in Malaysia, Kavitha and I had moved to Singapore. I was happily managing a part of a very large project for Standard Chartered Bank. It was a Credit Operations System that was spanning three countries — Singapore, Malaysia and Hong Kong. Singapore was great too. We had made a lot of friends and really there was nothing to complain.

That all changed one day.

It was a day when Alok, husband of my friend Sheenam (my colleague from CITIL days) came to our home. He was returning to India from Australia. Singapore was a stop over for him. While having dinner we talked about a number of things. He got to know my childhood, my interest in fiction and journalism etc. I talked a lot about my mega project at Standard Chartered Bank and that somehow did not impress Alok.

After about an hour, Alok said, “CP, you are a creative person. Why don’t you go to Silicon Valley?”

I responded immediately, “No Alok, the last few years we have lived in cities and I think we are comfortable living in a city. We don’t want to live in a valley.”

Alok started laughing and couldn’t control himself. I knew something was wrong. I asked him what was wrong and he had to explain what Silicon Valley was all about. I felt like an ignorant fool but beyond that it was a good education. Before he left for India, Alok urged both of us to think about what he told us.

Kavitha and I thought about this conversation for a number of days and finally one day we decided to try our luck. It took a few months to find a job (that’s another story some day) but it was all worth it in the end.

It’s been more than a decade living in Silicon Valley and most of my real career, building companies, writing business books, teaching courses for entrepreneurs everything happened here.

As Steve Jobs says, “We cannot connect the dots looking forward, we can only connect them looking backwards. “ Adding to that, my theory is that keep doing good AND continue to spread joy ALL the time and you will increase the chances of “right” dots connecting in the future.

Planned? Far from it. Serendipity? Without a doubt.

I can go on and on with dozens of stories but then it will become a big book by itself. So, I will stop here.

Things to Note:

Planning is always based on available information. If you are open to serendipity, there is always new information. Being open to serendipity is to keep going where you want to go but without the blinders on.

That’s the way it works. You and I know that there are far more options than what we can brainstorm and pin down anytime. Unless you walk down the path for a while and be open to looking around, you will not find these new paths.

I have found this time and again that completely surrendering to the present moment has innumerable benefits — one of the main ones being you observe a lot more as you are here and now. You are NOT in the future or you are NOT in the past. Serendipity blooms when you are living in the present. Try it for yourself and you will never want it any other way.

Written by

Entrepreneur, Author and Teacher, co-founder of Based in Silicon Valley. More about him at

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