My older son just started 1st grade. As expected with any kid growing up in the Bay Area, he is already being bombarded with tons of activities – from soccer classes & cricket camps to music classes, karate & regular play dates. This is in addition to a school schedule that to me, already looks super intense.

Just 2 weeks into the new school year, I have been compelled to bring up the importance of prioritization with my better half. With work commitments & regular school duties, there is only so much a kid and 2 working parents can get done in 24 hours.

My humble submission to the family has been that we need to be smart in picking our battles. Essentially, have the kid gradually start focusing on a few areas, instead of spreading himself thin.

This predicament has prompted me to look back at my own career and reflect on what I have experientially learned about this topic both directly while executing in my jobs as well as indirectly by observing others around me. In particular, what I have gathered from working with and studying founders & investors I have come to respect.

Reflecting on my journey – the ‘discovery’ part

Growing up, I was the kid who always wanted to try out a variety of things and experiences. Even for a specific school project, I would boil the ocean, reading every book and resource I could get my hands on. While preparing for IIT JEE, I would read every reference book any friend recommended, and try and do every practice test series that looked even remotely relevant.

I carried this same behavior into my professional career. Over a decade and a half, I worked directly or indirectly in multiple sectors (oil & gas, software, medical devices, consumer Internet, eCommerce, SaaS, etc.), dabbling in multiple functions (finance & investment banking, product, operations, strategy, BD, partnerships, etc.), operating across multiple regions (US, India, China, SE Asia, etc.) and stages of maturity (founding my own startup, Series B startup, tech conglomerate, institutional VC, operator-angel).

Luckily, I figured out last year that venture investing is my true calling and this type of career design actually feeds really well into pursuing it professionally. Be it public or private markets, the best investors have a diverse set of mental models and best practices from many different fields meshed in their heads. This helps them to connect the dots in unique ways while evaluating any opportunity, thus giving them the proverbial ‘edge’. The best example of this is Charlie Munger. PS: I wrote about how he thinks in ‘Munger’s Tao‘.

Having a rich tapestry of experience across many areas definitely helped me develop a unique ‘strategic 360⁰ product leader’ positioning as an operator vis-a-vis my peers, and is now helping me carve my path as a venture investor.

Coming back to the earlier retrospective exercise, though this story so far made sense, a specific question still kept bothering me – “Have I missed a trick by not focusing deeply enough on any one area?”.

As we operate in a cluttered and flat global marketplace where everyone has access to almost the same information, and it has become easy to create shallow narratives in any area, I started questioning whether I had peanut-buttered my career to my own detriment.

Reflecting on my journey – the ‘focus’ part

During discussions with some of my friends, mentors, and especially my better half, an interesting nuance hidden in my story was uncovered. Even while hopping across many fields, countries, and skills, the one parallel constant in my life’s equation was venture investing. Since stepping into VC for the first time in 2011, I continued to go deeper into it, studying and practicing it over the subsequent decade.

For 10 years – I read every Fred Wilson blog. I made everything Paul Graham said about building a company from scratch on his blog and Twitter my religious text. I listened to everything Peter Thiel had to say about competition, Reid Hoffman about network effects & Vinod Khosla about building long-lasting companies.

While working at a VC firm, I went to obscure cities & events where no other investor could be seen. I did full-day boot camps across the nation to demystify venture capital for founders at the grassroots, even when it was unlikely that any of them would be fundable deal flow for the firm.

During 2011-13, when Indian VCs were yet to discover Twitter in a mainstream way, I was one of the most active investors on the platform, trying to replicate the playbook of Valley VCs on it. PS: credit to Shradha of YourStory for encouraging me to get on Twitter during those early days. Twitter has added value to my world in ways that are hard to quantify.

Subsequently, when I stepped out of the VC world and became an operator in the Bay Area, I continued deploying my salaried money into early-stage startups each year, a majority of which was invested in the first round at an idea stage. By the way, this was before it became fashionable to become an angel during ZIRP.

While working intense continent-hopping jobs, I continued to get on calls with founders at 2 AM, trying to work on strategies to save a company on its last breath. In between building products and founding a startup, I strived to keep making myself better as an operator-angel by studying the journeys & frameworks of the likes of Semil Shah (totally in love with his blog), Elad Gil (substack), Jason Calacanis (love his old but raw Angel Podcast episodes), Ron Conway & Pejman Nozad.

Purely as a result of following my natural curiosity, I had inadvertently ended up focusing and going extremely deep into the craft of venture investing.

Balancing ‘discovery’ and ‘focus’

Connecting the dots now with my kid’s 1st-grade predicaments, there is an idea here from my journey that I believe is relevant. Careers (and life) are about a balance between ‘discovery’ and focus’. While conventional wisdom talks about the importance of each in silos, I have come to experience that a healthy mix of both is needed to design a thriving career and live a fulfilling life.

It’s important to have enough room to discover – try different things & test different ideas, while still striving for focus and actively looking for leading signals that indicate what to focus on.

The relative proportion of discovery and focus will be dependent on each person’s context. While most kids and youngsters will naturally have a high proportion of discovery, we also know prodigies tend to start focusing really early in life (Tiger Woods took to golf at 6 years of age; Warren Buffet bought his first stock at age 11).

People in the middle phase of their careers typically tend to gravitate more towards focus, trying to climb the ladder at a specific company or type of job. A counter view would be that many of them would do well to increase the proportion of discovery in their careers, in order to get to a global maxima.

Folks in the latter phase of their careers organically become experts at something, thereby increasing the proportion of focus in their lives. A view worth considering here is whether increasing the proportion of discovery in their careers might help avoid getting jaded and bring in fresh perspectives into their field of expertise.

There are no right or wrong answers here. Everyone will need to find their own balance considering their holistic context – age, location, family structure, social setting, and economic circumstances. Although, just based on a sample size of 1 (i.e. my journey), is following your natural curiosity a good way to organically evolve an optimal mix of discovery & focus? Perhaps…

PS: check out this podcast clip by Naval Ravikant, elaborating on “specific knowledge is found by pursuing your curiosity“.

Visually representing discovery vs. focus

To close out, I would like to share a pictorial representation of this idea of balancing discovery and focus. I tend to think of ideas & mental models in terms of pictures; I guess there is some merit to that age-old wisdom of “a picture is better than a thousand words”.

To me, this balance can be represented as a free-flowing river being directed by its banks. The middle of the river is in discovery, having enough room for the water to go in any direction, form vortexes, change color, and experiment with constituents like soil, mud, rocks, etc. But, the banks give the river focus, ensuring it stays on a desirable path, moving within specific boundary conditions and ultimately, meeting its true calling of merging into the sea.

As a parent, I hope to be the river bank that provides focus to my kid’s discovery. As you reflect on your own journey, how might you strike the balance between discovery and focus in your career and life? Are there areas where you feel the need to freely discover more, and others where honing your focus could lead to breakthroughs? Would love to hear your insights and experiences in the comments below, or on LinkedIn and Twitter.

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