Advice to my 18 year old self!

Advice to my 18 year old self - as a real-life “slumdog” in Silicon Valley!

I was born in Guduvancheri, the southern burbs of the suburbs of the city of Chennai in Tamil Nadu, India. The Tamil word “cheri” in Guduvancheri literally means slum. 45 years later, I find myself as a founder/entrepreneur in Silicon Valley.

I’m not a big “advice guy”! Context-free advice is not just useless, but can be dangerous. I’ve noticed that many advice seekers only want to reinforce the decision that they’ve already taken (I’ve been one too).

But, I’ve been getting a few requests during my coaching/mentoring sessions on what advice I would give not to them but to myself - my 18 year old self.

I agreed to write it even though I’m confident that my 18 year old self would read these as platitudes and not truly understand. So, here goes this week’s multidisciplinary post.

Table of Contents

• Ego is the enemy

• Don’t chase growth without development

• Via Negativa

• Unlearning > Learning

• Reading vs Thinking

• Complex systems require oblique interventions

• Decision Register

• Bonus Advice

• Appendix: Book Recommendations

Ego is the enemy

When I reflect back on my life, as I find myself here in Silicon Valley as the founder of a startup, at the age of 45, I must confess that two things punctuated my entire life and career - luck and failures. Mostly just luck/chance/randomness.

I have no sense of pride about my career - only gratitude about how lucky I have been - to have awesome managers who were supportive of my crazy ideas, to get the opportunities that I got, etc.

I’ve realized from the bottom of my heart that I got to where I am because of mostly random chance. Not because of my talent, skill, intelligence, grit, perseverance, knowledge, etc.

There was a point in time where I used think some of those things mattered the most and as a result my head was full of ego. But, as the area of the island of your knowledge grows so does the perimeter of your ignorance. Sometimes you have to know enough to know that you don’t know enough.

To clarify, I’m not saying you can ahead in life without skills or specialized knowledge. Things in life are always multi-factorial, but the most powerful factor is randomness and it is very easy to overlook that.

(Books have been written about this and so I don’t want to spend 20 pages explaining this with anecdotes from my life. While this post is open access to all curious subscribers, the serious subscribers will get access to the reusable template of my decision register and book recommendations towards the end.)

Learning about systems thinking and complexity profoundly changes your life. A new worldview emerges as you transform as a person - it is a messy cybernetic dance. The best way to explain this transformation is through stories:

For students of philosophy: Plato’s Cave.

For Movie lovers: The Matrix.

I’ve worked with and met so many VPs, SVPs, CXOs, founders and executives over my 23 year career. One common thing that prevents them from learning is their own ego. Epistemic Humility is a rare trait.

Here’s my advice: You will take the red pill a few times in your life and completely change your worldview on many things. This type of transformation will rock you to the core - but remember to become more and more humble in the process. As you rise through the ranks, as your wealth and reputation grows, remember this:

Don’t chase growth without development

Don’t go through life without learning the difference between growth and development. I’m not a fan of providing “definitions” for words so that we can standardize them - but instead we must give our own descriptions and have back-of-forth conversations about what those words mean to us. End of the day, it is the listener that determines the meaning of an utterance. Ackoff’s descriptions resonated with me the most on this topic:

There will be times in your life where you will face the option to choose between money and learning - from your very first job. But, listen to your grandmother’s advice and choose learning. Her advice was in the form of Hindu mythological stories - she told me that Lakshmi, the Goddess of Wealth, won’t stay with me, if I ignore Saraswati, the Goddess of Knowledge.

Even when I got the job offer to move to Silicon Valley from another state, the math was very clear - after accounting for cost of living and high taxes, I’d be taking home far less money than what I was already making. Of course, I tried to negotiate, but when that failed, I moved with no regrets. I figured how lucky I was to have a job in 2009 when so many people I knew were getting laid off and evicted from their homes amidst the global financial crisis. More importantly, how lucky to get paid to live and learn in the frontier of Tech!

Via Negativa

I used to be the person that optimized my life for happiness and would actively seek new things that I thought would make me happy (new games, movies, etc.)!

But over time, it became clear to me that this was a fool’s errand because I still felt miserable. I then inverted this problem and started eliminating things that made me miserable instead - but, I wish I took this approach much earlier from my life.

The changes ranged from getting rid of my blunt kitchen knife to moving to a new city; from exiting certain WhatsApp groups to breaking up relationships that drained my energy.

I became meticulous about removing things from my life that caused misery. As a result, the baseline happiness in my life significantly improved.

Now, how does this insight apply to other aspects of life and work?

Improving productivity is not about improving productivity by adding things (like AI)- it is about removing friction that impedes flow. That’s where the best bang for the buck is!

Similarly, a person worried about their health outcomes must first focus on removing things (quit smoking) rather than adding things (artificial sweeteners in their coffee).

Smartness isn't about being smart - it is about NOT doing dumb things. Keenly observe all the dumb mistakes (addiction, envy, leverage, debt, keeping up with the Joneses, etc.) adults around you make and just avoid them.

Unlearning > Learning

Unlearning (error correction of what I already knew) has given me the best ROI (Return on Investment) over learning new things. But again, what gets in the way of unlearning is also ego. As the saying goes, faced with the choice between changing one’s mind and proving there is no need to do so, almost everyone gets busy on the proof.

This manifests in many ways. The first person to escalate to a leader gets on their “good” side - the other person ends up doing a lot of explaining. Many leaders don’t pause and think “What if the other person escalated to me first?”

The later we meet someone, the more negatively we describe them. Watch this pattern unfold when you are interviewing for a job. If you are lucky to be the first and become a strong contender, you become the baseline. After you, it becomes a matter of “are the rest better or worse than you”.

Never fall for this trap! Being a fallibilist and being willing to change your mind when good explanations come forward has profound advantages.

Reading vs Thinking

Most people read themselves to stupidity. I chuckle when people publish a collage of all the books they’ve read so proudly at the beginning of each year.

People stuff their mind with useless facts and figures - the capital of country A, the population of city B, etc. But, they don’t spend time to think about what they’ve read and develop understanding of fundamental human nature, the complexity of the world we live in, etc.

We read many subjects in silos - that’s how our schools and colleges have been structured - into various classes and departments. But, the real magic is in the synthesis - putting things together. The thinking part involves connecting the dots.

The most important part of reading a book, is the thinking that follows. But, I’ve observed that most people don’t do it.

Many consume their book as an audiobook in 2x speed or read the TLDR “cliff notes” version (e.g.: Blinkist) and completely miss the profound insights from it.

Here’s my advice: Chase topics you are interested and focus on learning - go down rabbit holes and remember that you don’t have to complete every book you pickup in your hands.

There will be years where you don’t finish ANY book, but learn a lot. Read fewer but older books (aka Lindy books) over and over. More importantly, make room for solitude in your everyday life - to think.

Complex systems require oblique interventions

The goal is not the goal. The side effect is the real goal!

Parents who command their children and ask them to do stuff “because I said so”, only get short-term compliance. But, raising kids that can make their own decisions throughout their life is a completely different ballgame. The same goes for leadership.

Don’t become a command-and-control “leader” who seeks quarterly profit margins with direct actions - laying off people, consolidation/centralization of functions to gain “efficiency”, reducing buffer inventory, creative accounting practices, cutting corners - where quality & security suffers, etc. Be ready to experiment with counterintuitive and anti-mainstream ideas.

The shortest distance between two points is a straight line. But, the longest distance between two points is a shortcut. But, many leaders sacrifice the long-term for the short-term - those decisions eventually come back to bite the organization for sure.

Even in personal life, we all “know” we must exercise, eat healthy, sleep well, etc. But, only when you try to change yourself you’ll understand the true you. You need to deal with the emotional side of you that tries to maintain the status quo.

Setting a numerical weight-loss goal and killing yourself at the gym is never the long-term answer. Sustainable behavior change is very tricky without intrinsic motivation and a change in identity.

While the abstractions of knowledge, understanding, wisdom, etc. break down at some point, I will give a description from my own journey so that you can make your own meaning:

If you have knowledge, you know.

But, if you understand, you act!

This involves understanding of the self.

Decision Register

Every decision has both intended and unintended consequences. Your decision making failures fade out if you don’t keep track. A decision register helps in this regard… It serves two main purposes - to prospect the future and retrospect the past.

For example, many value investors decide to invest in a certain stock because they formulate specific hypothesis about the business. In the future, when that changes or gets disproven, the stock may continue to rise because of market insanity. But, the prudent investors that kept a log of why they invested in the first place sell and exit their position. The emotional ones that don’t, eventually crash and burn.

Similarly, leaders in a corporate setting make a lot of decisions but forget to log WHY they made certain decisions - Reorgs, Mergers & Acquisitions, Defunding/funding certain projects, Promoting individual A vs B, Partnering with company A vs Company B, etc.

But, when those decisions bomb they don’t seem to learn any lesson from it. They continue to make more poor decisions and focus on ensuring their own survival or jump ship, while their people and customers suffer.

Also, remember that ‘acts of omission’ are also decisions. For example, Nokia not investing heavily in the smart phone business early on is also a decision.

Here is a simple ‘decision register’ I’ve used for over a decade. Click the link below to download the template and use it - both for personal and work related decisions. Keep a log and learn profound lessons from it.

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