#6 - 10 Lessons Learned: Navigating 15 years of my work life

Insights and Milestones: Things I wish I had known 15 years back.

I still vividly remember the day (27th Jan 2008) I got placed at Invensys. As a mediocre student in Chemical Engineering, I was constantly under fear of not securing a job offer. It was a great relief. I was ambitious and wanted to make a mark in the world and prove that I am not a failure. So job was at hand but I was not sure what would I do at real job.

Now It has been almost 15 years (7th July 2008) since I commuted to the office for the first time. Today, I'd like to share some of the lessons I wish I had learned before starting my career, lessons that I often talk with my team. It's the guide I wish I'd had when I began my journey. I hope it will benefit you in the ways that it would’ve helped me

Journey is the destination. So enjoy it.

1. Optimise Broadly; Minimize regrets - A change in perspective

Recently I came across the concept of optimising the life broadly instead of narrow optimisation. If one wants to be at the top 1% of the population, he or she needs to sacrifice or optimise the life around that one. Be it career, money or power. You achieve what you focus and optimise for. Instead, if you try to be at the top 10%, you have higher probability and also you can be at top 10% on your career, money and happiness. It means coming in terms with being not great at one thing but good at many things.

When I started my career, only thing I thought of is how to progress through it faster and grow faster, make more wealth etc. By looking back, now I see how much I have lost on the way. I could have travelled more, spent more time with family and see so many lost opportunities which would have made my life more meaningful.

2. It is my job to find a good manager - Power of a good mentor

Good managers are good teachers and it is a two way relationship.

When I embarked on my career journey, the significance of having a "good manager" was often emphasized, yet its true meaning eluded me. I mistakenly believed that likeable and experienced individuals automatically equated to effective managers. Furthermore, I assumed that I had no say in determining who would become my manager. It was my responsibility to seek out a good manager, if I wanted one.

If you've spent more than a few months working alongside me, chances are you've heard me speak of Sitakanta Ray. Although our manager-employee relationship lacked formal sessions, we engaged in conversations that spanned life, work, and everything in between. Through our interactions, I learned the essence of genuine care, team respect, leading by example, and much more. These invaluable lessons and first principle thinking, acquired during my tenure at MySmartPrice, have shaped my leadership style and continue to serve me well to this day. I credit my professional growth to the discovery of such exceptional manager throughout my tenure.

3. The Subjectivity of Success: Running Your Own Race

Promotions and titles, often seen as benchmarks of growth or success, are merely arbitrary measurements shaped by someone else's standards. Looking back, I truly wish that someone had reminded me during my early days to stay focused on my own journey. Such guidance would have spared me countless nights of anguish and introspection, those "one of those days" when I was plagued by feelings of depression and frustration about the direction of my life.

Even now, I grapple with this issue. Changing the definition of success at a subconscious level proves to be a difficult task. While part of me still yearns for conventional success, I have grown wiser and learned to brush it off, shifting my focus towards what truly matters to me at present. Now I run my own race. Trust me, life is not a sprint but a marathon, so plan accordingly.

4. Learn, Persevere, Execute; Embrace Action, Avoid Over-planning

I’ve always been an over-planner. I used to map out my two-year plan every six months in my mind. Many are aware about the dozens of domains which I bought over the years to work on my ideas but never saw an IP address attached to them. Countless hours were spent immersed in planning, envisioning the success of specific ideas and imagining how they would transform my life and personal growth. But overplanning stressed me out when things inevitably didn’t go according to plan. Every setback felt like a personal shortcoming, a sign that I hadn't exerted enough effort. Then I would overcorrect by planning even more when, in reality, many things were beyond my control.

Looking back, even if those ideas did not achieve commercial success, I now wish I had persevered and executed on a few of them. They would have undoubtedly provided me with valuable lessons along the way. Unfortunately, I am currently learning these lessons the hard way.

5. Celebrate Your Wins: Fueling Growth Through Thoughtful Recognition

During the initial month of my very first job, the Head of India centre shared how he planned out to reach that level by his age of 35 and told us proudly how he achieved it over a drink. That left a mark on me.

Throughout my career, I experienced rapid growth. At the young age of 28, I built a team from the ground up at MySmartPrice. Later, I seized another opportunity, starting anew, and by the age of 33, I held the position of CTO in a $500 million company. However, I realize now that I never truly celebrated these achievements. Here I am at 35, embarking on a fresh journey from zero.

I have come to understand that thoughtful celebration is not self-indulgence; rather, it is a powerful tool for sustaining long-term growth. It allows me to break free from the relentless pursuit of perfection and the grip of imposter syndrome. Now, I ask myself if the "me from a decade ago" would be proud of who I have become today, and I celebrate the fact that the answer is a resounding yes.

6. It is a very small world: Nurturing Connections That Span Time

Like interconnected puzzle pieces, our paths often intersect in unexpected ways.

This has become my favorite phrase, one I share with others when they depart from my team or when I bid farewell. I must admit, I haven't always excelled at maintaining professional and personal relationships once the everyday interactions stops. It's not because I fail to recognize their value, but rather because I don't actively invest effort into staying in touch. However, despite the passing of time, I hold onto the sense of connection, as if no hiatus had occurred, when I do eventually reconnect with someone after years.

I have come to a realization: the world is remarkably small. We continuously encounter one another, whether as future colleagues or mutual connections sharing our workspaces. While there are ethical reasons to cultivate good relationships with fellow humans, it becomes even more crucial when considering the potential impact on one's career, which can be influenced for better or worse by these connections.

7. Building Bridges Through Giving

In the past, I found myself hesitant to reach out to individuals whom I deeply respect and admire. While my more confident peers confidently approached and introduced themselves, I would often remain in my seat, assuming that these experienced individuals wouldn't lend a helping hand because I had nothing tangible to offer in return.

However, as cliché as it may sound, I have come to realize the importance of giving, and giving more, before asking for help. In the past six months alone, I challenged myself to break free from the grip of imposter syndrome and the belief that I had nothing of value to offer. I began to open up and engage in conversations with people, recognizing that genuine connection can bridge gaps and create opportunities for mutual support. You always have something to offer to someone.

8. Check your values instead of boxes - Navigating Life's Path with Purpose

For the past 15 years, I meticulously tracked my bucket list, diligently ticking off each item on it. Score well in school, attend a reputable college, secure a decent job, climb the ladder of success, and eventually become a leader—I moved from one box to the next. However, things changed when the next box, such as writing a book, doing a side project, clashed with desires and aspirations that weren't neatly listed. I found myself struggling to maintain motivation.

Upon leaving MySmartPrice, I believed that happiness, learning and growth awaited me in larger, structured companies. Yet, that notion lasted less than two years, and I found myself drawn back to the excitement and thrill of the startups.

Reflecting on my most significant life decisions, I've discovered that the best choices were often guided by intuition rather than logical reasoning. For instance, leaving Amazon to join a pre-series A company with a significant salary cut proved to be a great move. Now, I am once again left the well-paid CTO role, pursuing my next calling starting at zero.

When I first heard Steve Jobs' Stanford commencement speech in 2007, connecting the dots didn't resonate deeply with me. However, as time passed, I began to see how those dots interconnected and shaped my journey.

It is easy to follow well laden paths that don't align with our true selves. Asking myself what I truly value has been a challenging endeavor because it requires honesty about my own definition of success. Though I still face struggles in this regard, I've learned that when I find myself at a crossroads, it's crucial to check my values. Only when I understand what truly matters to me can I chart a path that leads me there.

9. Manage your energy and optimise for happiness

I heard Naval Ravikant, the former CEO of AngelList, say that his number one priority in life—above his happiness, his family, and his work—was his health. I began to understand the profound truth behind the saying, "You can't pour from an empty cup.”

Energy and attention, not time alone, became the valuable currency that I learned to safeguard and invest wisely. Activities that I once believed I had no time for—such as exercising, taking leisurely walks, and socializing—became my top priorities, essential investments in recharging my mind and body. I grew conscious of the unconscious habits and behaviors that drained my energy and consumed valuable mental space, like endless rumination. If I found myself engaged in something I disliked for an extended period, and had no control over it, I made a deliberate effort to free myself from it. By managing my energy, I discovered that I could utilize my time more meaningfully and productively.

Understanding the profound link between energy management and overall well-being has enabled me to optimize my life for happiness. By replenishing my energy reserves and channeling them into activities that truly matter, I've unlocked a greater sense of fulfillment and purpose.

10. Career is a portfolio; Avoid getting attached.

Like a diligent gardener tending to a flourishing garden, your job is to create the ideal environment, exert the right effort, and provide the necessary circumstances for growth. Just as a tree that falls ill requires pruning and replanting, it's crucial not to become overly attached to a specific project or product. Attachment can cloud your sense of purpose and hinder progress. By adopting a mindset of balance, dedication, and adaptability, you can nurture your career, focusing on learnability and maintaining fertile soil for future bounties.

In the early stages of my career, I viewed my work output as a personal expression, taking offense if a product failed. I also believed that my career would follow a linear path, where success was guaranteed over time.

Whether it's in our careers, investments, or life as a whole, the probability and magnitude of success are inversely proportional—an idea I'll explore in another post. Additionally, luck plays a significant role in shaping outcomes. Therefore, it's essential to make multiple small high probable bets, increasing the probability of success. For instance, I could have started a newsletter a few years ago or continued writing my book, creating more opportunities and increasing the odds of success.

Approaching our careers as diverse portfolios allows us to embrace new possibilities, adapt to changing circumstances, and seize unexpected opportunities. By staying open-minded and embracing the role of a gardener, we can cultivate a fulfilling and dynamic professional journey.

Few things which I did right (I guess)

Leap into the unknown and shine your brightest

Reflecting on the past 15 years and connecting the dots, I realize that I wouldn't be where I am today without making a few daring decisions to leave the well-trodden path and embrace the unknown. Back in 2012, I departed from CTS to join a small startup with only three people operating from a 100 sq. ft. penthouse room. It turned out to be one of the best decisions of my life. Once again, leaving the comfort of Amazon and taking more than 75% salary cut to join another company and deciding over a phone call may have seemed daunting, but it allowed me to learn and grow. While this path may not be for everyone, I attribute my willingness to take these leaps to my upbringing by my parents and the support from my wife.

Your team is more than mere numbers

I have always hated referring to engineers or individuals as "resources." Humans are complex systems with unique qualities. Treating people as mere numbers diminishes their value. Everyone deserves respect. Empathy and compassion set us apart from the animal kingdom. It's important to recognize and leverage the strengths of each team member. It's unrealistic to expect immediate behavioral changes in individuals who have been shaped by 20+ years of their own experiences, both inside and outside of work.

There have been instances in my life where I made mistakes and experienced regret and guilt afterward. In the years 2014-2015, I focused solely on my work and assumed that my colleagues shared the same approach. I became frustrated when they didn't exhibit the same level of commitment or willingness to work as I did. I decided to take matters into my own hands, believing that it would prove my capability. However, truly getting to know my team as individuals helped me not only accomplish tasks but also become a better teammate and leader.

I am proud and confident to say that most of my team members still reach out to me, seeking career advice and considering me a mentor. I must have done something right. (Have I?)

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Navigating the early stages of my career was often perplexing and isolating, but I found it easier with great people who were on a similar journey. Through it all, I've come to realize that the journey itself is the destination. Instead of striving for some future state of nirvana, I've learned to embrace and enjoy the present. The start of your career marks the beginning of everyone's journey, and I hope my experiences can offer guidance and support to someone else along the way.