How do you go about solving problems?

My father grew up playing chess in his native country of the Philippines, where the game is hugely popular. He became fairly skilled, and even won a few tournaments in the Navy after immigrating to the U.S. Of course, he was eager to teach me, his firstborn son, the rules of the game.

As a young child, I had an extraordinary interest in strategy and problem solving--and I firmly believe the love for chess that my father instilled in me contributed greatly to that.

Recently, I came across the following video. It beautifully captures a moment in New York City's famed Washington Square Park, where a trash-talking older man realizes he's been beat by an international grandmaster:



Maurice Ashley, the gentleman who won the game, just happens to be the first African-American International Grandmaster inducted into the U.S. Chess Hall of Fame. Ashley is passionate about sharing with others how the principles of chess can help on the larger stage.

"Chess changes lives," Ashley says in a documentary he filmed for Mashable. "I see it in students that I teach. I've coached kids in Harlem, in Brooklyn, in circumstances that are not easy...I've watched those exact same kids take the benefits of chess, the character building effects of chess--whether it be critical thinking, better problem solving, better concentration, better focus."

"And they've taken them and gone on to universities, top universities around the country, and gone on and gotten great jobs and great careers."

The Trick: Working Backwards

Chess is a great metaphor for life and business, if nothing else because of the sheer possibilities for variety the game presents.

For example, there are over 300 billion possible ways to play in the first four moves alone. There's a myth, explains Ashley, that Grandmasters can see up to 20 moves ahead. 

But it's only a myth. Kind of.

In an excellent TED-Ed talk Ashley gave at TEDYouth 2012, the expert shares a few techniques that give Grandmasters this apparent superpower to "see into the future". His favorite strategy--both in chess, and in life?

Retrograde analysis. Otherwise known as: working backwards.



"What you do with retrograde analysis," says Ashley, "is that in order to look ahead, it pays to look backwards."

Why is this so useful?

In chess, as the game continues forward after those initial four or five moves, the position of the pieces begins to get simpler. Pieces start to disappear. Eventually, when good chess players compete, the game progresses to a relatively "simple" position--one in which only a few options remain.

"[Grandmasters] like to study things like this," explains Ashley, "so that if we get to them, we know how to play them 'cold'...but also, so that we can steer the position that's in front of something this easy."

"So, in this way, when you're dead, I already knew like 10 moves ago. Because I knew where we were going."

Putting It into Practice

So, how do you apply this to your work? Here are just a few possibilities:

Plan your project backwards.

Many are in the habit of planning a project beginning with step one. But this often leads to a problem: More time and money are scheduled for early steps than is really needed. Then, the later--often more important steps--become rushed.

Instead, plan your project by working backwards from the final steps. This will enable you to allocate proper time and resources to help ensure a better end result.

For example, by creating a stricter budget and set of deadlines for beginning steps and allocating "extra" time and money for more important areas, you attain a more realistic view of the work and can eliminate the tendency to waste precious dollars, along with days and even weeks.


We are taught that more is better. But in business, that's not usually true.

Having too many choices can be paralyzing when it comes to decision making. Instead, aim to narrow things down whenever possible. It may be possible to sell a thousand varieties of a product, but how many will be truly interesting to most customers?

Of course, there is a place for flexibility and "tailor-made" solutions, but you should also try to simplify these as much as possible.

Steer things to your advantage.

Every organization and individual have specific strengths and weaknesses. By identifying these, you can often steer circumstances to your advantage.

For example, if you've got an infectious personality and are a great presenter, find a way to get that to as many people as possible. Maybe you can invest in making a professional video that will take advantage of spreading that enthusiasm.

Or maybe you're more introverted, but you happen to be very creative or an excellent writer. Work towards finding opportunities to use those strengths--for example, reach out to guest post on popular blogs or find another platform to showcase your work.

Similarly, if you know you're weak in a certain area, steer the ship to avoid situations where you could be exploited.

Making the Impossible, Possible

Retrograde analysis is a vital problem solving skill, but it works like any ability: You don't get good at it overnight. In life, just as in chess, it still takes:

Practice, practice, practice.

If you stick with it, learning to work backwards can help you develop better critical thinking skills--and the ability to solve your most pressing problems.

And in the end, you just might learn to see the future.