Short and Long Games

Chess and checkers.

They’re the original table games. They’re tests of skill and strategy. And they take place on the same board, filled with squares of alternating colors.

Yet, that is where the similarities end.

Chess caters to the sophisticated. There are several types of pieces for the players to use — each of which has its own movement patterns. That means there are plenty of permutations to consider.

Success in chess means seeing five moves ahead better than your opponent can. It’s all about the long game.

Checkers, by contrast, is less complex. The pieces look identical, and their movement patterns are relatively straightforward.

Success in checkers means reacting appropriately in the moment. It’s all about the short game.

These table games each have ardent fans. Yet, that support doesn’t tend to overlap across contests.

Perhaps it should.


The discrepancy between chess and checkers seems like an amusing bit of annoyance. It feels similar to the debate about whether to put ketchup or mustard on a hot dog. (The answer is clearly mustard, by the way.)

But look deeper, and this dispute marks an important cultural schism.

For we like to divide our society into different groups. Rich and poor. Liberal and conservative. Old and young.

And yet, one of the most tantalizing divisions involves time horizon. It separates the short-term thinkers from the long-term ones.

Long-term thinkers are seen as visionaries. They can help our society prepare for the future or endure an uncertain present. But they don’t necessarily thrive in the day-to-day.

Steve Jobs, for instance, was a legendary long-term thinker. He ushered in an era of consumer-friendly computing and he helped spark the shift to smartphones. But he famously wore the same outfit to work most days, and he didn’t have a great rapport with his workforce.

Meanwhile, short-term thinkers are seen as practical. They can provide consistency, helping to keep things running in the day-to-day. But when there’s a paradigm shift, they might not be equipped to react.

John Antioco, for example, mastered short-term thinking — leading Blockbuster Video into the new millennium as the king of video rentals. But Antioco infamously turned down an offer to purchase Netflix around that same time, helping lead to the company’s decline.

There’s a longstanding debate about which school of thinking is more beneficial. But truth be told, they both are.

It’s important to maintain a vision for the future, and to have a sense of direction. But it’s also critical that we remain available to meet the needs of the moment.

And so, our society is split into two types of roles. Those in strategic positions help chart the road ahead. Those in operational positions keep the gears turning.

This split has paid dividends on a wide scale. But if you look deeper, it’s clear that this divide is failing us.


In my younger days, I would have considered myself a short-gamer.

I preferred checkers to chess, and I took plenty of stock in the needs of the moment.

This had nothing to do with spontaneity. Indeed, I have always been a planner.

But my plans were both practical and immediate. I didn’t have the energy to worry about what would happen five years down the road. Surviving the day was much more important.

This approach helped me excel in school, and it allowed me to navigate some lean financial times in early adulthood. But it also made my choices rigid.

For instance, if I stepped on the scale and didn’t like what I saw, I’d work out until my legs felt numb. If my bills were too high, I’d run the air conditioner less often. And if the scene at work got hectic, I’d stay late to get everything taken care of.

Days tended to compound on each other. So, this extreme approach did help me build long-term habits. For instance, I’ve built up an exercise regimen and eliminated both alcohol and sugary drinks from my diet in recent years. All those changes originating from a short game approach.

That said, devoting myself to such a pattern left me blind to the bigger picture. I had no idea where I was headed, or what I could do if my arbitrary choices failed.

This became apparent when I switched careers and moved to a new city. Making such drastic changes was in my best interest. But taking a chance on me wasn’t high on the list of priorities of prospective employers. And so, I languished, stuck in neutral.

I eventually gained a foothold in a new industry. But this only happened after I’d lived in an extended-stay hotel for three months and after I’d maxed out my credit card to cover food and gasoline.

In the aftermath of this experience, I started thinking about the long game. I considered where I wanted to end up, and how far I was from that objective. As I progressed through my new career and enrolled in business school, such concerns fueled me.

But switching approaches would prove to be no easy feat. Short-term thinking was all I knew. Now, I was asking myself to toss it aside and start anew.

I struggled to let go.

Then, a global pandemic put everything on pause. And in that moment of quiet self-reflection, I finally saw the light.


What you do today determines who you will be tomorrow.

Chances are, you’ve heard words like this. Maybe from a parent, a sports coach, or a professional development guru.

This advice is meant to bridge the gaps between the short game and the long game. It’s designed to make us intentional of our actions and aware of their consequences.

This all sounds great in theory. But it rarely works in practice.

For we do not have full control over the future. Unlike the chessboard, the world is volatile. Good short game fundamentals might position us for success, but they won’t necessarily get us across the threshold.

My past misadventures all but prove this point.

To see success, we must turn that advice on its head. We should rephrase it as follows:

Think of where you want to be tomorrow. Then consider what you can do today to help get there.

Such advice gives us a clear North Star. And it puts all our actions in service of that North Star.

No longer must we be wedded to rigid habits and routines. If the path to our objective becomes untenable, we have the liberty to try another approach. This flexibility can improve our chances of reaching our goal.

And yet, we remain accountable to the here and now. For our actions serve as building blocks, bringing us closer to our North Star. Without them, our path to success is gone.

The short game and the long game can work in tandem. But only if the long game leads.

This epiphany has led me to rethink everything. It’s made my decisions less rigid and my strategic vision more resilient. Best of all, it’s made me less apprehensive of the future and the uncertainty it brings.

So yes, it’s time to put the chess and checkers debate to bed. The short game, the long game — they’re just pieces of the same puzzle.

It’s up to us to put those pieces together.

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