After graduating with a Computer Science degree in 1999, I joined Wipro Technologies as a Software Engineer at a time when India’s tech and outsourcing industries were growing at breakneck speed.

One of the popular projects that virtually the entire Indian IT industry was working on at the time was called Y2K; the year 2000 problem, or the millennium bug, was caused due to the fact that calendar data was represented as 2-digit years versus 4-digit years (YY vs YYYY) in many software systems that were built during the days when memory was expensive. Imagine billing systems or interest computation modules of a bank which use dates to calculate duration and the implication of having ’00 instead of 2000 as your date. This is a good example of missing long-term thinking in systems design.

Our inability to predict and plan for the very long-term was fresh in my mind, as my final year project was to implement the IPv6 protocol, which was going to replace IPv4 addresses (Internet’s unique addressing mechanism to identify a connected device) as the world was running out of what once seemed like an inexhaustible 4.3 billion addresses (this eventually did happen in Feb 2011). Thinking and planning for the long-term is a difficult problem indeed when it comes to systems design.

In part 1 of this series, we saw why it makes tremendous sense for companies and individuals to play the long game. But in part 2, we explored how, in practice, it’s incredibly difficult, despite the many advantages. In this article, we will discuss what strategies and approaches may enable us to play the long game. For companies, this may be about building an enduring business; for individuals, this may be about leading a fulfilling life.

“When we intend to play the long game it should come with the realisation that the players will change over time.”

How to play the long game
  1. Start with the “why”: Simon Senek, in a book titled “The Infinite Game”, talks about how infinite players play to stay in the game and finite players play to win. The need to stay in the game is a powerful motivator to play long and one that needs a “just cause” or a “strong why”, Sinek explains. The ‘why’ is our purpose. And we need a sense of purpose to serve as a compass through long journeys which, undoubtedly, will be marked with uncertain times. If there is a strong mission or sense of purpose, there is usually high motivation to remain in the game for long. Jaydeep and Kallol, the cofounders of Rebel Foods (formerly Faaso’s) kept iterating on their model since their launch in 2003, until they invented and scaled the multi-brand cloud kitchen play, because they were intent on delivering on the mission to transform the way food is prepared and delivered to achieve great customer experience.
  2. Find intrinsic motivators: We meet people that play different sports, but if you’ve ever met a golfer you’ll know how deeply passionate they are about their game. I have often thought about why golfers are so obsessed and why everyone I’ve met has highly recommended the game to me. My view is that golfers are intrinsically motivated because it’s a “me against myself” kind of game and such a pursuit is perpetual, as you don’t play to win. You play to improve. There isn’t a destination, per se – it’s the journey that keeps you hooked.

    As individuals or companies, if we focus on extrinsic motivators like valuation or winning against competitors, such things could end up as short-term milestones versus fuelling your core mission to play the long game. Getting to #1 may be a good motivator, but once you achieve the goal, staying at #1 needs a stronger purpose to keep going. Byju Raveendran doesn’t want to stop working the 18-hour days because he feels he has barely made a dent in making high-quality education accessible to everyone in the country. Despite his decacorn status, he often says, “If I think I have won, the game is over for me!”
  3. Play with discipline, intentionality and consistency: If you ask any serious cricket test player, they will argue that the source of success in test match batting is to play with discipline and intent, and in knowing exactly which balls to leave. This requires patience and the willingness to be consistent in how you apply yourself, session after session. Playing long games is more about mental toughness and playing with some rules in mind – to be able to see the long-term and to orient towards that with the decisions you make without getting tempted to show short-term results that distract from the real game. Startup founders often ask the “growth vs. profit” question and the answer should come from understanding where your long-term ability to deliver on your mission will come from – dominance through market position or ability to be around in the long-term through fiscal discipline in an industry that’s not winner takes all.
  4. Create longevity through culture: When we intend to play the long game it should come with the realisation that the players will change over time. Leadership will undergo a transition over time and the new leaders will continue to pursue the mission. It’s important that companies and individuals give this adequate thought and plan for such transitions intentionally. This also builds a culture that puts the mission ahead of individuals. When Sequoia Capital’s founder, Don Valentine, set up our firm, he did not name the firm after himself but after the mighty Sequoia tree, which is known for its longevity. He also ensured that there was a smooth transition of the leadership to Doug Leone and Sir Michael Moritz when the time had come for the next generation to take over. By then, the new leaders had imbibed the culture of Sequoia and had become stewards of the institution and the brand.
  5. Adapt constantly: When Sequoia partnered with Go Colors, a women’s leg wear brand, we made the case based on the insight that Indian culture, which has been subject to centuries of invasion by outsiders, has kept itself relevant by absorbing western or eastern influences and making it its own. Go Colors was benefitting from the mix and match culture of urban working women who liked the convenience of a legging matched with the rich heritage of a salwar. Ethnic apparel in India is an example of how culture evolves to internalise influences without resisting it, thereby creating room to remain in the game. Playing the long game means adapting and evolving with the changing environment. For individuals, this means investing in upskilling to remain relevant and being open to new experiences, and for companies this means adapting and re-inventing itself to the changing needs of their consumers.
  6. Find the right partners: Naval Ravikant speaks about the value of playing the long game with long term people. This is so important and something that’s not usually given enough thought. Whether it’s a choice of a VC investor or the business partner/co-founder you decide to embark your journey with, finding people who want to play long is critical to ensuring you are able to make the right choices without pressures and vested interests. How many founders probe potential investors on whether or not they face pressure to show returns and hence may push for an early sale of the business vs. building it to an independent company in the long-term? As individuals, we typically choose a life partner who is aligned on long-term issues, like what a fulfilling life means or the level of commitment towards having kids, versus focussing on whether you like the same type of movies. Surround yourself with advisors who share your vision and values, and who can provide you the perspective that comes with experience.
  7. Eliminate extraordinary risks: In 2006, after 1,428 years of existence, the world’s oldest business – Kongo Gumi, builder of Buddhist temples – went into liquidation. They collapsed after loading up on debt they couldn’t service. When playing the long game, it’s important to play with some margin of safety and to not bet the house on things that could take you under. This could be debt or speculative investments, or unethical dealings for short-term gains. I have heard of companies defaulting on commitments because they took aggressive treasury calls and invested in equity and lost significantly when this was not their core business. For individuals, doing anything that can kill trust, hurts your ability to play long.

Finally, it may be helpful to create rituals and formats that remind us just how long the game we are playing actually is. In his book “The Clock of the Long Now: Time and Responsibility”, Steven Brand talks about how the Long Now foundation is building a 10,000 year clock inside a mountain in western Texas as a reminder to humanity to think and plan responsibly for the long-term. This seems to have the support of Jeff Bezos, the man who believes that Amazon should perpetually be in Day 1.

As I write this article on 09/11/02021 (if you did notice the extra zero that’s because I learnt from Steven who wrote dates in the DD/MM/YYYYY format, that this is a way to accommodate 10,000 year thinking!), I do hope many startup founders who aim to build enduring businesses find your “just cause” and play consistently and long enough to allow the power of compounding to help you build something meaningful that serves your core mission.

“As individuals or companies, if we focus on extrinsic motivators like valuation or winning against competitors, such things could end up as short-term milestones versus fuelling your core mission to play the long game.”

Recommended Reads

Here are three articles I read over the last few weeks that I found interesting:

What slime knows, is a long read, but if you are as curious as I am about this basic life form, which seems to have some innate intelligence, then this article is a must read.

The history of boredom might surprise you. This short read by Jessi Damiani explores how boredom became a thing and how attitudes towards boredom have evolved over time. To some of us, boredom feels like a luxury we are willing to pay for once in a while!

The Locker Room, by Ted Lamade, is yet another reminder to us about how culture determines success of companies and how teams that work in sync can deliver more than individual superstars. Also, I learned there is indeed a correlation between Glassdoor ratings and actual stock performance!

If you have time for a longer read, here are two books I’d like to recommend:

The Long Game: How to Be a Long-Term Thinker in a Short-Term World, by Dorie Clark.

This book was released recently and since I had just completed writing this series I was curious to read the book and check if there were overlapping ideas or if there were things I could learn. Overall a good read and it provides a more practical approach to how to focus and be at it to be able to play the long game. I particularly liked the idea of “strategic patience” discussed in one of the chapters.

How to Change, by Kathy Milkman.

I am really interested in behavioural economics as a topic, so it took me little time to buy this book, released a few months ago. I listen to Kathy’s podcasts and reading this book was like an extension of the conversations she hosts. She covers interesting topics like “temptation bundling” and “implementation intention” and covers interesting research behind such concepts. It’s an easy read and one that I enjoyed.

Do write in at if any of my interests intersect with yours! Click here to read more articles on Peak XV’s blog. I’m also on LinkedIn and Twitter.