How do you go about solving problems?

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

This love of chess, instilled by my dad, led to a great interest in strategy and problem solving, even at an early age. 

Fast forward to today. I recently 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 how the principles of chess can help on the larger stage of life.

"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 and gotten great jobs and made great careers."

The trick: working backward.

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

For example, there are more than 300 billion possible ways to play in the first four moves alone. There's a myth, says 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 backward.


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

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."

In essence, working backward doesn't just solve problems--it helps prevent them from appearing in the first place.

Putting it into practice.

Ashley's advice isn't new. As he points out, retrograde analysis is used in fields like law, science, medicine, and even the stock market.

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

Plan your project backward.

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 initial steps than are really needed. Then, the latter--often more important steps--become rushed or under-funded.

Instead, plan your project by working backward from the final steps. This enables 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 is often 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 truly interest your 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 has specific strengths and weaknesses. By identifying these, you can often steer circumstances to work for you, instead of against you.

For example, if you're a great presenter and have an infectious personality, find a way to get that to as many people as possible. Maybe you can invest in making a professional video that will help you spread that enthusiasm.

Or maybe you're introverted, but you happen to be very creative or an excellent writer. Work toward 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 those weaknesses could be exploited.

Making the impossible possible.

Retrograde analysis is a vital problem-solving skill, but it works like any ability: You don't become great overnight. In life, just as in chess, the following holds true:

Practice, practice, practice.

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

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