How to Succeed in Life? Play Chutes and Ladders

In our last post we discussed how inspirational quotes in social media are not inspiring the right behavior. Well, you would be forgiven for thinking this entry is the antithesis of that post. Here we dive into the lessons we learned from the childhood game Chutes and Ladders, and how learning to find the ladders all around us in plain sight is the secret to every success story ever written.

How Playing Chutes and Ladders Taught Me Everything I Needed To Know About Succeeding in Life

On the ladders of life, some people are at the top of their ladder, some are in the middle, still more are at the bottom, and a whole lot more don’t even know there are ladders at all.

Learning “Truths” Is The Easy (and Dangerous) Part

When I lived in Kazakhstan for a few years as a Peace Corps volunteer I was introduced to some interesting “truths”. For example, if you sat at a table’s corner, you would never be married. If you were a female and sat on cold concrete, you would never get pregnant. And if you shook hands across a doorway you would be plagued with bad luck forever.

I call them “truths” rather than superstitions because everyone I met believed them to be as true as they believed the sun would rise tomorrow. Silly, right? If you were born and raised in the United States you would likely “know” they are 100% wrong about what they believe to be true.

But then Germans believe that if you wish someone a happy birthday before their birthday you are bestowing upon them a year of bad luck. And if you want to ensure a year of good luck, break a plate on your wedding day. They are clearly wrong about both, right?

Salt was so prized as a preservative and seasoning for food, that spilling it was considered grossly unlucky. Thus the Sumerians around 3,500 B.C. created the practice of throwing a pinch of it over their left shoulders.

And then Mexicans believe if you sweep over your own feet you’re destined to marry a widow. My question is if the widow you are destined to marry is already a widow when the sweeping happens, or if the sweeping instructs the universe to first take a life before introducing you to their surviving partner.

(I actually don’t know if I want to know the answer to that.)

Mexicans also “know” that if you hold an image of Saint Anthony upside down and ask him to help you find something lost, he will help you find it. And when you find the lost item you must then place him right-side up or risk losing the item again.

When I was growing up we didn’t have any pictures of saints in our house, but we were instructed to say “Saint Anthony, Saint Anthony, please look around. Something is lost. May it be found,” until we found the item. It only had to work once for us to believe there was some “truth” to it.

And it rhymed, so that was fun.

Make Them Rhyme So They Go Down Easier

Speaking of rhyming, we also sung nursery rhymes with ignorant smiles on our faces, unaware of what we were actually saying by repeating the words.

Ring Around The Rosie? Blissfully ignorant to our celebration of the Great Plague in London in 1665, an outbreak of bubonic and pneumonic plague that brought death to over 15% of London’s population. Ashes to ashes, and all…

Poor London. London Bridge Is Falling Down? Did you know that the foundation of the bridge was composed of buried children to help watch over it and maintain its sturdiness, and that it requires more children else it will crumble–or so goes one of the many mythological origin stories of the rhyme.

And Eeny Meeny, Miny, Mo? Well, the “tiger” in “catch a tiger by his toe” wasn’t always a tiger. What we would timidly refer to as the “n-word” today was the original lyric. And this was taught to us by our school teachers and parents. Did they not know, or know and not care?

But as children, we are completely oblivious to the fucked up and nasty shit contained in what we are taught. As our brains are developing and as we are fed “truths” (we are going to keep that word in quotes for a while), they become the bricks in the house that is ultimately our character.

Once those bricks are set, and we continue building on top of them, unlearning those “truths” becomes a difficult and often painful task.


UnLearning “Truths” Is The Hard (but Necessary) Part

However, questioning your “truths” is an essential skill if your chosen path is continued growth and becoming a better version of yourself every day.

Think about what you know to be true. And I don’t just mean “think” are true, but deep in your bones you “know” without any hesitation or doubt that it is unequivocally true.

Here are some examples of what people “know” to be true:

  • God [exists or does not exist].
  • The [political party of your choice] is the best party.
  • Climate change [is real or is not real].
  • The death penalty is [just or unjust].
  • The best form of government is [insert form of your choice].
  • Life begins at [insert when].
  • Breaking Bad is the [best, or something less than] television show in history.
  • When waiting to enter a place, you are standing [in line, or on line].

What are the chances you are correct on every one of your “I know to be TRUEs”? Zero. Nil. No chance whatsoever you are right about everything you believe to be true.

Isn’t it worth our time, then, to question what we may be wrong about? (If your answer is “no”, then you may as well just stop reading…get a cookie and go be right about everything in your dark corner of what you are calling reality.)

The most important skill an adult needs to learn once they are through with their formal education is how to effectively (and selectively…that’s the most important part) unlearn what they just spent over a decade being fed by other people. If we cannot master that, and do so relatively early in our adulthood, we are destined to become one of those assholes we love to complain about.

What If I Am Wrong About Everything I Know?

I have spent the last few years (really, since crossing the 40-year-old marker) struggling with the following question: What if I am wrong about everything that I thought to be true?

Not just some of my truths. Not just particular truths. But every truth I believe.


As I got older, some of the “truths” I thought were absolute began to show fatigue. In the same way a lifetime con-artist just gets tired of the charade when death comes knocking because, well, what’s the point any longer?

For starters I grew up believing that I was supposed to prioritize my formal education if I was to expect a good job and good pay. Follow the rules, do what you’re told, and you will eventually be better off than those who broke the rules and never listened to authority figures.

And then I met individuals who never went to or finished college, who broke many of the rules I had been taught, and were further along in their careers than I was. Who were making far more money than I thought was ever possible for me. Who were fuck ups in school and somehow seemed further along professionally, financially, than I was. And loving what they were doing far more than I was.

I grew up being taught that it was smarter to get hired by a “good” company than to think I was smarter than said company and start my own business. After all, what was I going to when [insert the hundred negatives my then-teachers cautioned me on]?


And then I met and worked for individuals who did just that, took risks and started their own businesses, and got rich in the process while I worked for them.

I grew up believing that my love for creative writing should remain just a hobby, not something I should seriously think would put food on my table or pay my rent. That to pursue writing as a career was foolish, and I should just get a “real job”.

And then I turned 40 and looked back on my twenty years of “real” jobs, my twenty years of making other people rich, my twenty years of following someone else’s rules, and realized I had the wrong teachers. I didn’t know the right truths. I had been following the wrong rules.

What Are Rules and Why Are They Important

Oxford says rules are statements of what may, must or must not be done in a particular situation; of what is possible according to a particular system; or when playing a game.

Violate the rules and there are usually penalties. If there weren’t any penalties, the rule would be less a rule than just a suggested guideline.

For example, our parents have their unique rules of the house and their set of consequences. Like, “your room needs to be clean or you don’t get to go outside and play“. The consequence to not cleaning our room is being denied the right to play outside.

Our parents also decide what other desired behaviors will not have specific and immediate consequences. For example, it wasn’t a “rule” that we couldn’t eat the seeds of a watermelon; it was just a suggestion: “Don’t eat the seeds or a watermelon will grow in your stomach.

Rules Provide Structure

Rules can provide the following (among other things, I am sure):

  • Safety
  • Protection for those who are too weak to defend/protect themselves on their own
  • Trust
  • Predictability and consistency

But imagine a world without rules:

  • What if you could drive on the sidewalk?
  • What if anyone could take anyone else’s stuff?
  • What if anyone could take the life of anyone else they felt like?
  • What would sports or bad sitcom TV be like without rules?


But Everyone Has An Opinion On What Is “The Right Structure”

Learning which rules to break is important, since not all rules make any sense or would be considered by any sane individual to be just. Think about the rule we had back in 1776 about taxes and tea, and what would have happened had a few courageous individuals not decided to break that one?

But it’s hard to imagine breaking all of the rules we have set up for ourselves. Especially those established to ensure safety, protection and trust for all (note I wrote “all”; we can all point to rules that are meant to ensure those things for only one set of people while exploiting another group of people). And the ones that help direct a life of morality and good character should be inviolable.

Christians have their Ten Commandments, which include rules the non-Christian world also abides by such as not being able to murder or steal. Hindus have their Twenty Ethical Guidelines called yamas (restraints) and niyamas (observances), which include rules for good moral conduct like adherence to compassion and steadfastness in our pursuits.

The Buddhists have their Ten Precepts which speak to abstentions from using intoxicants, committing sexual misconduct, and taking what is not given to you. The Confucians sum up most moral conduct with their golden rule: Do not do unto others what you would not want others to do unto you.

But we can also look outside of the major religions for rules that govern general humanity.

Religious Rules Are Not The Only Game In Town

The Beatles gave us the rule that All You Need Is Love. Winston Churchill, Albert Einstein, Martin Luther King Jr. and Mother Theresa were all said to be avid believers of the Law of Attraction.

Sir Isaac Newton is among many scientists, mathematicians and philosophers who have discovered universal “laws” (another way to say “rules”), like the one that says: Your child will continue to be a misbehaving pain in the ass until you discipline him/her (otherwise known as the first law of motion).


And my personal favorite author of life’s universal rules, Dr. Seuss. Who can dispute “The more that you read, the more things you’ll know. The more that you learn, the more places you’ll go”? Or “Today you are you, that is truer than true. There is no one alive who is youer than you”? Or “Be who you are and say what you feel, because those who mind don’t matter and those who matter don’t mind”?

Learning the Secret to Chutes and Ladders

So what are the correct rules? What are the universal truths we need to live the life we imagine? And what rules or truths do we have at our foundation that are both false and rotting and keeping us from realizing that imagined life?

When you start down the path of questioning your “truths” and then begin to take steps to remove the false and rotting foundational bricks from your house, well you end up stumbling on your childhood in unexpected ways. And while I was traveling on this path I found myself thinking about the game Chutes and Ladders.

And one morning it seemed to hit me all at once.

Chutes and Ladders as a Morality Tool

Americans have been playing the game for less than 100 years (Milton Bradley released it in 1943, renaming it from its original Snakes and Ladders and having replaced the snakes with more playful playground equipment), but the game is over 1000 years old, invented sometime between 1200 and 1000 AD.

The original version of the game had snakes rather than the more playful and less intimidating chutes.

Originally an Indian dice board game that emphasized the Hindu philosophy of destiny (karma) and desire (kama), in all of its incarnations it has always been at its core a tool for teaching the consequences of good deeds versus bad deeds.

The ladders represented virtues (e.g. generosity, faith, humility). The snakes represented vices (e.g. lust, anger, murder, theft). The Indian version of the game had fewer ladders than snakes, emphasizing that the path of good is more difficult than a path of sin; while the English version had equal numbers of both paths (I’ll let you decide which was a more accurate rendering).

At the bottom of the ladders a child is doing a good deed, and at the top the child is enjoying the reward of the good deed. At the head of the snakes or chutes a child is doing something foolish or mischievous, and at the tail of the snakes or bottom of the chutes the child is suffering the consequences of their ill-conceived deed.

And the lesson of the game? A person can be saved by doing good deeds (ascending the ladders). But doing evil will cause you to be reborn as a lower form of life (descending down the snakes or chutes).

The board contains 100 colored squares, numbered 1 through 100, and the first player to spin their way to the 100th square is the winner.

The Milton Bradley version from my childhood.

Could Chutes and Ladders Be a Hidden Map for Achieving Success?

I was sitting at an outdoor cafe in Lyon, France several summers back, and struggling to order my breakfast. The menu was in French. I didn’t speak French. And every time I attempted to use my pocket phrase book to speak I heard “Je ne comprends pas.”

I don’t understand.

At the same time my stomach was wondering if I had died or forgotten how to chew, I was thinking about a quote I had been bouncing in my head all year: “To achieve what you never have, you must do what you have never done.

I had used this quote as my source of strength for almost a year. It was what I whispered to myself just before I quit my job, and then just before I enrolled in wine school, and then again when I bought a plane ticket to Italy without a return flight.

And so I called upon it again on this particular morning. I asked the cafe’s server if she spoke English. (I had promised myself I was not going to be one of those Americans in France who expected the French to speak with me in English). She did, and I finally got some breakfast.

Had I tried that the night before, I may not have gotten weird looks when I attempted to order tarte à la mode and then attempted to complain they forgot the ice cream (in French, à la mode just means fashionable…no ice cream). And was thoroughly confused by how small my entrée was (the word in French actually means an appetizer).

A Lightbulb Goes Off in Lyon

Ok, so every time I consciously and with purpose embarked on something I had never done, I achieved something I had never had. And the opposite happened when I didn’t. As long as I continued at the same job, thinking the same thoughts about how it would be stupid to quit without having another job lined up, nothing new happened. None of the things I believed I wanted ever happened.

And that’s when the proverbial “IT” hit me. 

In just a year, by attempting to make “To achieve what you never have, you must do what you have never done.” my guiding principle in all decisions, I managed to move myself further along then I had in the prior ten years by remaining at the same job, doing the same thing. 

I imagined my life as though it were a game. And that I had just jumped over a number of spaces. Like spinning your way in Chutes and Ladders onto a space with a ladder that jumps you forward. Moves you past the other players around you who didn’t have the fortune of landing on that space with the ladder.

And that my game (humanity’s game) was full of ladders. Spaces that, if you happened to land on them, would jump you forward, moving you past the other players, and further than you would have been had you not found yourself on a space with a ladder.

Step Through The “What If I Am Wrong” Process

So I began by asking myself the question: What if I am wrong about everything that I know?

What did I think I know?

I know that Chutes and Ladders was just a game, nothing more. But what if I was wrong?

What if there was something hidden in this 1000+ year old game that once found would reveal a lost truth (or set of truths) otherwise unseen by the masses? What if this game was designed to teach more than just morality, and doing good deeds vs bad deeds?

I know that life is random; there is no universal playbook with rules that if learned allows us to consistently navigate life better than others. But what if I was wrong?

What if there is a universal Success Playbook. And what if it is thousands of years old? And what if it transcends religion, and nationality, and any other dividing characteristic we employ today? 

I know the multi-billionaire college drop outs I admired for their successes (e.g. Bill Gates, Mark Zuckerberg, Steve Jobs) are the exception, not the rule to successful stories, and that to otherwise achieve what they have should require a higher ed degree. But what if I was wrong?

What if these supposed exceptions didn’t just get lucky, were in the right place at the right time, had a particular upbringing that created an advantage, just worked harder than anyone else, etc. but actually identified an intentional path, a specific rule or rules that if they just adhered to would guarantee their success? 


Now Pressure Test Your “Ladders” Theory

1000 failed experiments before Thomas Edison invented the lightbulb. How did he do it?

Michael Jordan cut from his high school basketball team before becoming the GOAT. How did he do it?

Walt Disney fired from multiple ventures because he “lacked creativity” before revolutionizing animation and building an empire (that has since destroyed Star Wars for me, but I digress). How did he do it?

Steve Jobs fired by his own board of directors before becoming, well, Steve Jobs. How did he do it?

They all learned where to find, or how to build, the right ladders. The path that enabled them to defy all popular judgement, to surpass all generally accepted “truths” believed by others.

Example Ladder:

None of the massive successes we value are born from ease—they are born from adversity, from failure. If you are not failing, you are not trying, and if you are not trying no measure of success will be possible. Learn how to fail effectively.

Johannes Gutenberg creating the printing press and changing the way we retain and share knowledge, literature and music, creating our modern form of education, and giving way to libraries and bookstores and the crushing weight of useless paperwork at the office (thanks Johannes!). How did he do it?

The Wright Brothers building and then flying the first fully practical airplane, giving humans the ability to do what they had never done in their hundreds of thousands of years of existence. How did they do it?

Roger Bannister breaking track and fields most notorious barrier, what had been deemed physically impossible, by running a mile in less than four minutes. How did he do it?

They all learned where to find, or how to build, the right ladders. The path that enabled them to defy all popular judgement, to surpass all generally accepted “truths” believed by others.

Example Ladder:

To achieve what you never have, you must do what you have never done. And all of the best things in life are on the other side of your maximum fear. Learn how to overcome the fear of doing what you have never done.

The Playbook on How To Always Succeed Is Nothing More Than a Collection of Ladders

So that morning in Lyon I began to call the universe’s inviolable maxims, rules, strategies, absolutes, the certainties in life that are infallible, as ladders.  I saw these ladders as the keys to unlocking the doors that enable us to navigate the world.  Like on a Chutes and Ladders board, I was understanding the ladders as the tunnels, the hidden passageways, the express trains, that move you forward and through (if not around, under or over) the complexities and strifes and confusions that other people struggle with overcoming on their way to their personal successes.

Michael Jordan was cut from a basketball team that had a dozen other players the coach thought played better basketball than Jordan. But Jordan found the right ladders that allowed him to surpass all of them—and where none of them managed to discover or learn how to achieve any comparable athleticism, despite playing the same game as Jordan and having seemingly a better advantage (e.g. not being cut from the team).

Roger Bannister was one of thousands of track and field runners who all had the same athletic bodies, who all studied the same historical athletes, who all were indoctrinated in the same absolute truth that the human body could not surpass the 4-minute mile. But Bannister was able to discover a path to achieving what every expert in his field agreed was physically impossible. 

We know these stories, and we use terms such as grit, and determination, and can-do attitude, to explain the possibility of the impossible happening. We listen to speeches about the importance of hard work, of pushing beyond our limits, and of never quitting. We hold up athletes and military leaders and business icons as examples of living the habits we need if we want to be successful.

And while all of that is sound reasoning, solid advice, what if…just what if…there was something else? What if there was also a set of universal, transcendental ladders that once discovered, learned, or if needed built, allowed us to advance beyond what others would say was possible?

And what if these ladders were not inaccessible to us, but just hidden waiting for a discerning and committed eye to find them? 

Most people do not achieve their potential.  Most people do not believe they are capable of greatness.  And I think that is because they have never found a ladder, never learned that if they just build one for themselves they can indeed climb over their current obstacles and get closer to realizing their greatness.

And that is the lesson Chutes and Ladders has taught me. For over a thousand years there has been a tool available to humanity for understanding how to successfully navigate the world. The design is simple. Learn the ladders—what they are, where they are, and if one does not yet exist learn how to build it and then go build it. 

We all start out from the same position on the Chutes and Ladders board, and have the same number of spaces ahead of us. Some of us find the ladders left behind by others, or learn how to build our own ladders, bypassing what everyone else struggles through. Some of us slip down a chute and either jump off early, or upon hitting the bottom bounce back up and keep moving forward, committed to finding or building our next ladder.

Life is not a mystery. It’s a game of Chutes and Ladders. The ones who win are the ones who do one thing better than anyone else. 

The learn the ladders.

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Published on: July 18, 2022  -  Filed under: Life Lessons  -  Tagged: , ,

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