October 1

Color Outside the Lines: Why It’s Okay to Break Some Rules

There are three categories of people in this world: rule followers, rule benders, and rule-breakers. I firmly belong to the first camp—the followers, the kind who would rather not color outside the lines. You draw lines; I’ll stay well within them. You tell me what is and isn’t acceptable, and I’ll do my best to obey. No reminders necessary.

It’s no wonder, growing up, I was the quintessential low-maintenance kid. I was well-liked by people in positions of authority—teachers, supervisors, and in general, by all adults, I interacted with. In contrast, my likeability factor amongst peers, especially those keen on bending or breaking the rules? Not so much. I was seen as the boring spoilsport, the one who tended to conform rather than challenge.

Friends couldn’t get why I was so intent on always dotting the i’s and crossing the t’s. And truth be told, I was unable to fathom why someone would struggle to follow the rules. Why were they, such troublemakers? Why could they simply not color within the lines drawn for them?

The impasse lasted many years (decades, even.) But with age comes wisdom, and with wisdom come epiphanies. I have since learned a few valuable life lessons. Especially this: it’s not always what it seems. Allow me to explain.

Template culture

The systems around us are seemingly designed to reward rule followers. We like kids who do their homework and turn in assignments on time; we prefer to hire people who show up at work and say the right things; we like to hang out with folks in social settings who get on well with everyone and generally tend not to ruffle any feathers.

As a species, we are great at making up rules and templates. We create rule books and guidelines on "how to be" and are often suspicious of anyone who deviates from the template or tries to color outside the lines. There are two good reasons for that.

1. Survival

We are a social species, and our very existence has always depended on cooperation rather than dissent. United we stand, divided we fall. Indeed, there would be utter mayhem if we let everyone act according to their whims and fancies.

2. Ease

Rule followers usually have attributes we label as desirable — conscientiousness, self-discipline, and the ability to take directions. These behaviors are encouraged because they create more manageable people and don’t cause headaches for those in positions of authority.

When the template does not work

That said, we take the game of adherence and compliance a little too seriously. We end up drawing arbitrary lines and expect others to never color outside these lines. But this quest for perfect acquiescence keeps us from taking risks, leaving us moored in our comfort zones. If there’s one thing we can all agree on, it’s that life begins outside the comfort zone.

In his 2017 book, Barking up the wrong tree, author Eric Barker says,

Following the rules doesn’t create success; it just eliminates extremes—both good and bad.

Not what rule-followers want to hear, right? Yet, we still like to raise kids who play by the rules. Name one parent who does not want their child to get good grades and be class president?

But, since not everyone can become class president, what happens to the kids that don’t? Are they less successful later in life compared to their presidential peers?

The answers will surprise you.

Contrary to popular perception, the world is not run by rule followers. Instead, it is run by outliers.

The outliers

These are people who deviate from the norm. They are simply different. They tend not to be well-rounded. Some are exceptional in their chosen field but lacking in many others. They are the specialists, not the generalists. The hedgehogs instead of the foxes. They are the ones who do not hesitate to color outside the lines.

Outliers are the creative types with offbeat, oddball, and sometimes even off-putting ideas and behaviors. Their leaps of imagination are really what move the human race forward. Without them, we all risk becoming robots, or worse, Stepford wives—pleasing, but devoid of personality.

But, here’s the thing about outliers. They act, think, speak, dress, and may look different from those considered “normal.” They can be awkward to interact with. Uncomfortably so.

But instead of finding ways to deal with our discomfort, we are on a mission to normalize the outliers. We want to convert them from their extreme into our average. That can have troubling consequences.

I had a professor in college who routinely disparaged the concept of average. His favorite quote was,

A man with his head in the fire and feet in an icebox is said to be on the whole comfortable.

Averaging data to explain concepts is usually a cop-out. Averages don’t tell us the real stories. The juicy and exciting details are often hidden in the extremes. It’s a similar situation with the outliers.

Trying to moderate the outliers is an exercise in futility. Our time would be better spent figuring out how to be more comfortable and receptive around the outliers instead of trying to woo them over to the "normal" side.

Resist the urge to convert outliers

So, how do we stop ourselves from judging others for their nonconforming behavior? Or, for that matter, how can we learn to be an outlier instead of an average Joe or Jane?

Here are three key behavioral traps to watch out for. If you find yourself indulging in these, it’s time to press pause and reflect.

1. Always done this way

I typically stay away from sports anecdotes, but here’s one that illustrates the point beautifully.

Football is a rough, dangerous sport and requires a high degree of discipline and commitment from its players. The training, therefore, has to be commensurately hard-hitting. Players need to be in beast mode—all the time. These were the unwritten, but clear rules for coaching college football teams.

But there was one person who didn’t buy the above arguments. His name was John Gagliardi.

Gagliardi was the football head coach at St John’s University who did things a little differently. His coaching philosophy differed from the traditional, often sadistic methods used to coach college football.

There were no loud whistles to assert the coach’s dominance. He did not withhold water from the players to toughen them up. To prevent injuries, he disallowed tackling in practice. His practice sessions never lasted longer than 90 minutes.

Gagliardi pretty much singlehandedly rewrote the rule book on how to train college football athletes. “Winning with no” was Gagliardi’s philosophy. And it served him well. So well, that Gagliardi is by far the most successful, or as they say, the winningest coach in the history of college football.

When Gagliardi took up the job of coaching, he started by eliminating all the things he disliked as a football player himself. Initially, his decisions didn’t sit well with those who hired him. His choices were questioned. But then the results started to speak for themselves, proving that Gagliardi was on the right track. It didn’t take long for him to win over his skeptics.

The lesson here: It’s okay to attempt to color outside the lines. It’s okay to question the status quo even when you’re told things are always done a certain way.

2. Looks weird

Walk into the produce section of most mainstream grocery stores in America. You’ll be greeted with row upon row of perfect-looking, shiny produce. Store displays are an art form aimed at creating visually appealing produce using color and shape synergies. What you won’t find are the misfits, the ugly produce. Odd-shaped carrots, discolored oranges, scarred apples —basically anything that isn’t alluring to the eye is discarded.

Corporate America is great at spotting niche opportunities. In the age of sustainability and to be on the right side of the fight against food waste, new companies were quick to capitalize on the ugly produce industry. Now, many companies sell produce boxes containing misshapen and flawed produce.

It is a capitalist win-win success story. The ugly produce industry makes buyers and sellers feel like do-gooders, purports to reduce food waste, and is lighter on the wallet.

The crazy thing is that, by its very nature, the ugly produce is probably closer to a real fruit or vegetable in its nutritional content and taste than its genetically modified, perfect-looking supermarket cousin.   

Discarding something of value just because it doesn’t look the part is a rookie mistake. Appearances are deceptive. This is how we miss the forest for the trees.

3. The right thing

Dorothy Shaver’s early career as a 7th-grade teacher was abruptly terminated in 1914 because she, with three other single female teachers, had attended a local dance, unchaperoned. (Oh, the horror!) Eventually, Shaver moved to New York and found a job (a stupid job, according to her) at Lord and Taylor in 1921 in the “comparison bureau” (spying on other stores’ prices.) From there, Shaver rapidly rose to be the President of the organization in 1945, becoming the first woman in the United States to head a multimillion-dollar firm.

Dorothy Shaver (1893-1959) was a trailblazing entrepreneur who shattered the glass ceiling before the term was even created. She was a nonconformist and a dreamer. In 1953, as she presented Einstein with the Lord and Taylor award for nonconformist thinking, she said:

If the world is to go forward, we must continually produce new ideas, new expression, new hope. Yesterday’s dreams are today’s realities, and yesterday’s dreamers, today’s authorities. This is as true in business as in archaeology, in medicine as in aviation, in philosophy as in television.

Einstein, for his part, gratefully accepted the award, alluding to himself as "an incorrigible nonconformist.”

Societal norms do change with time.  It’s quaint and frankly appalling to even think there was a time when unchaperoned single women weren't welcome at dances . The right thing yesterday may no more be the right thing today. And the only way to find out is by ruffling some feathers and questioning the status quo.


Any essay on nonconformist thinking would be incomplete without mentioning the master of the unconventional—Steve Jobs.

Apple’s Think Different ad campaign under Jobs’ direction has earned its cult status for a reason. The words are  powerful and spot on.

Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules… You can quote them, disagree with them, glorify or vilify them. Still, the only thing you can’t do is ignore them because they change things… they push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.

So, the next time you see a child, a coworker, or a friend acting or thinking unconventionally (okay, weird), try not to rush to judgment. And if you are that person, well, you don’t need any further convincing, right?

Be wise. Know yourself. And think twice before you judge.

It’s okay to color outside the lines. You don’t have to always fit in. It’s okay to disagree and ruffle feathers if you strongly believe in something because what is right can in and of itself be a subjective call to make.

And don’t bother with average. 

The average of an elephant and a mouse is a cow, but you won’t learn much about either elephants or mice by studying cows -  Lawrence Dworsky, author Probably Not



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