Why I left my cushy job to work for myself In the middle of a pandemic?

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In Aug 2020, I left my cushy job as a senior engineer at Uber and work for myself in the middle of a pandemic and a looming recession.

To be honest, this was not sudden. Becoming an entrepreneur was always a dream since 2011. I think this is because of how my beliefs got shaped up over the years. It probably had to do with my father being a serial entrepreneur + some of my side projects got moderate traction + me spending years in the silicon valley + me believing entrepreneurship is one of the best ways to learn about the world and contribute. But my finances were not good enough to give me ample time to start something of my own. In 2014, on the very first day to work for Uber, while walking from the SF Caltrain station 1455 Market St, I made a promise to myself - "This would be my last job before I do something of my own".

Fast forward to the next 5 years during which my professional and personal life made tremendous strides. I got married, traveled a lot with my wife, and relocated to India. On the professional side, I had a couple of promotions, a great rise in pay, and opportunities to build a new team. It was a quite satisfying job in most ways. The dream was still back of my mind but a great job and a peaceful personal life had dampened my enthusiasm. Almost 99% of colleagues and friends I was surrounded with had no such interests. The Tech sector is in such a boom that many top tech companies are literally showering engineers with stocks and money. Most of them were content with that. So breaking away from the herd felt scary. I started having second thoughts on why should I put myself through such hardship when things are just so great. While I was going through this confusion, Corona was declared a pandemic, and the world turned upside down.

Ultimately, in Aug-2020, I quit my job. Here is what led me to my decision -

1. A Builder's Mind

Answers to many confusing questions often come from within. I started introspecting my life and tried remembering what made me happy and proud in the last 10 years. While I remembered my graduation, salary hikes, promotions, etc, I realized most of my sense of accomplishment came from my passion project in all these years. I have a builder's mind. All my side projects were for solving a real-world problem using technology. I thoroughly enjoy learning and building stuff. I did so many side projects on a personal as well as the professional side until the last few years. In fact, much of professional success also came when my side projects eventually became mainstream at work. On the personal side, my proudest moments had come from reading the reviews of 5000+ random strangers who loved my transliteration app. And from a small invoicing/inventory management app based on a tablet that has been helping my family operate our manufacturing business post my father's death in 2012. That impact made, no matter how small it was, felt extremely rewarding.

But as I grew senior in a company, my roles and responsibilities changed. I had to focus more on consultation, cross-time zone collaboration, processes, goal setting, consensus building, and decision making, etc. I always saw these as necessary evils against something you do out of passion. I was spending more time on these and less time building new stuff. Working on side projects had gotten harder lately because of a demanding job and the necessity to maintain a good work-health-family balance. With the addition of a newborn in early 2020, choices became clearer. I cannot spend my personal time after office work to work on things I am passionate about to keep myself satisfied. I should quit my day job and work on passion projects and find ways to get paid for them. But is it too ambitious to do?

2. Rational Risk Assessment

One of the interesting points, I learned from Naval's podcast is

Starting a company has asymmetric risk. i.e. there are huge upsides and limited downsides.

If you make sure that you maintain a healthy life balance and not squander money, there are literally no other risks. Building a SAAS company has become easier than ever. Capital requirements are quite low. Access to capital is becoming easier. Hardware costs are constantly going down. Software building just requires a few laptops and time. You can sell your products globally. You may not always succeed in the first shot, but if you give enough shots, the probability of finding gold is good. And even if you don't, there is so much demand for good engineers that you can always fall back. In fact, if you have learned some new skills and met similar minded people along the way, you may land even a better opportunity than before.

But is it too risky to do this with a pandemic and a looming recession? These are actually good times to try out. The world is going through a massive transformation and is scrambling to find solutions for the new problems that arose after the pandemic. A mindset shift has kicked in. New habits are getting formed. The world will not go back completely to where it was before the pandemic. If you can put together something, you may get an early movers' advantage.

3. Compounding Effects

Knowledge and relationships have compounding effects. I had earned more money in the last 1 year than the total of the first 5 years of my job. This is because I had grown an expert and built good relationships in what I was doing. So just like they say in investing, time in the market is more important than timing the market. If you aim to be X in life, then starting as early in that direction as possible is more important than waiting for a perfect time to make a move. There will never be a more perfect time than now. If you think, someday you will have a mindblowing idea that you love to build with and would pay great, and you will have a great friend or partner who will also be equally passionate to do it with you, it's almost like expecting all the stars in the universe to align for you.

It is not necessary to have a good idea, a solid plan, and partners even before you begin. Just make sure you have enough financial cover for a reasonable time, say a year. In that 1st year, all you have to do is figure out something pays for monthly expenses and buys you another year of doing this. I know this sounds simpler than it is. But the internet has tremendous power and we have many such examples out there. One thing that I relate to most from the famous Steve Job Stanford speech is -

“You have to trust in something -- your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well-worn path, and that will make all the difference.”

With these thoughts, in July 2020, I quit my job. As I embark on this journey, I wish to meet new like-minded people, build new stuff with them, learn new skills, and enjoy new experiences. I am optimistic that I will find something I love to do and get paid for.

Writing these down, was important for me as a reminder every now and then of why I chose this path and share my journey with similar minded people. My heartfelt thanks to my family, friends, and colleagues who have been vehemently supportive of my decision.

To learn more about how this is going, follow me on twitter twitter.com/nilesh_mahajan

Comments (2)

Dinys Monvoisin's photo

This was a great article, very insightful. I will be pleased to know about your progress throughout the year.

Nilesh Mahajan's photo

Hey Dinys,

Thanks for kind words. I plan to write my progress on blog and share some stories on twitter here twitter.com/nilesh_mahajan