My last 10 years — Part 1

Vivek Shanmugasundaram
4 min readFeb 27, 2025

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The night before my birthday, I found myself wrestling with conflicting emotions. Call it a mid-life crisis or existential questioning. I’m not entirely sure which, but something was compelling me to reflect deeply on where I’ve been and where I’m heading.

I was sitting in my apartment in Bangalore. My career has grown from strength to strength in the last 10 years. If you have asked me 10 years back, I wouldn’t have imagined I will be doing so well. Earned decent amount of money, have good friends and family. Still Single. Love and Marriage seems to elude me in all possible ways. More or less I have given up on them now.

I find myself questioning the direction of my life. What’s the purpose of accumulating wealth and enjoying comfort when I don’t have a family (wife or kids) to share it with? Perhaps, I should use this freedom to do something else in my life. May be take a sabbatical and go for a world tour or become a full time Yoga teacher. Why not pursue both? So many questions, no answers yet.

While pondering this, I wanted to think about what I want to do in the next 10 years.

To better understand where I might go next, I need to reflect on where I’ve been. My career journey over these past 10 years has shaped who I am today, beginning with those uncertain months at Virtusa where I first realized corporate life wasn’t for me.

There is going to be lots of blabbering, so please bear with me.

Its been 10 years 6 months since I started working after my MBA.

When I graduated in 2014, I had an education loan, almost zero bank balance and absolutely confused what I wanted to do next in my life. But somehow I had that confident that I will figure it out. I have worked at 4 different startups (not counting my first stint) till now and every company helped me to learn (and unlearn)

Life at Virtusa Consulting (Jun — Aug 2014)

My corporate stint post MBA lasted just 3 months (including 1 month training in Hyderabad). The training was just a mix of different sessions and I was bored to death in that 1 month. Thankfully, Football World cup was going on and I always look forward to watching matches late night (Brazil time) and go to office sleepy-headed. Post my training, i was asked to join Chennai office at DLF Porur. I was staying with my friend Arengs in Adyar. I was asked to work on few UK/US based projects, but i was not too keen on them. So I was on bench for 2 months.

This was my schedule there

10.30 AM — Leave Adyar by bus or auto

11.15 AM — Reach office

1 PM — Go to near by Andhra mess with colleagues for lunch and eat full meals (No one can work after this)

2 PM — Nap time

3 PM — Complan time ( I used to bring Vanilla or Strawberry flavours in a dabba to office)

3.30 PM — Catchup with colleagues

4.30 — Leave office by taking share auto till Guindy and bus to Adyar.

I was bored to death during those 2 months. I know, if I stay at Virtusa, I will be assigned to some US project and they will ask me to travel and eventually settle down there, which I didn’t want. Also, I didn’t want to be an IT consultant.

In 2014, startups are slowly getting traction in India, but still its not B-school grads first choice because of high risk involved and not clear about what they do.

During one random conversation with my IIMB college senior, Venkatesh, I came to know he joined a e-commerce startup, Hopscotch in Mumbai and he asked me if I am interested.

Never heard about that company and I was shocked to know there is an e-commerce company only for Kids products.

He referred me and one thing led to another and I got an offer in 3 days time. Absolutely loved talking to my CEO, Rahul. Though they offered Product Manager role, I refused it as I didn’t understand what to do in that role and took up Analytics role as they wanted to build an Analytics team from scratch.

Life at Hopscotch (Sep’14 — Apr’16)

I was excited to move back to Mumbai (a city I absolutely love), though nervous about entering e-commerce with no prior experience. With blind faith, I took the plunge and joined Hopscotch.

The initial few months were extremely difficult. I understood neither head nor tail about each function’s role, and acronyms were flying around constantly.

After about 3 months, I began to grasp operations. Around this time, we hired Puneet as Head of e-commerce, and I started working closely with him. Having worked with several US startups, he was a treasure trove of information. Working under his guidance steepened my learning curve.

That said, he was one of the toughest managers in my career — a real taskmaster. Our good rapport ultimately helped me professionally. Over time, I understood what Product Managers do and wanted to transition into that role. Thanks to Puneet and Rahul, I began managing data products, eventually becoming a PM focused on Segmentation and Personalization. Though I loved working 14–16 hour days, my health deteriorated. Realizing this pace was unsustainable, I decided it was time to move on.

At Hopscotch, one of the best things that happened to me was the strong friendship I developed with Venkatesh, who had initially referred me to the company.

During this time, my sole focus was to do well in my career and learn as much as possible and quickly paying off my loans. I didn’t go on a single date during this period — in retrospect, one of the several mistakes I made.

You can read Part 2 here

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