Conquer Your Need for Rules and Embrace Adaptability

by Len Wilson

What if you had two sons and they came to you with a request to take a cross-country trip on their own? Would you let them? What if they were ages 10 and 6 when they made the request? Taking creative risks goes hand in hand with new life. If you want to be able to handle the future, I recommend you learn adaptability.


Texan Jack Abernathy was a U.S. Marshal and one of Teddy’s Rough Riders. He once ran down a prairie wolf on his horse, jumping on it and capturing with his gloved hands. Roosevelt later remarked that it beat anything he’d ever seen, and he’d seen a lot.

Abernathy gave his adventurous spirit to his two sons, Bud and Temple. In 1910, when Bud was 10 and Temple was 6 years old, the two boys decided they wanted to ride their horses from Frederick Oklahoma, to New York City, to greet Teddy on his return from an African hunting expedition. Jack said, sure, and gave them a few rules:

  • 50 miles a day, max
  • No water crossings without an adult
  • $5 max carry at a time
  • No Sunday travel

Jack wrote them a note to keep, stating they weren’t runaways. The boys left home in April with clothes, bedrolls, oats for the horses, bacon and bread. They slept outside, sometimes on the free and open range. On the way, they stopped at friends’ houses, such as Quanah Parker, the last chief of the Comanche. As they rode, word rode ahead, and after a while they began to be greeted by families who’d invite them in for a meal.

In New York, at the end of their journey, they met the future president. Roosevelt put the boys in the middle of his Rough Rider parade down Fifth Avenue. After the parade, the boys put their horses on a train back home. Jack bought them a car, and the boys – without the dad! – drove it back to Oklahoma.

10 years old and 6 years old.


It goes without saying… this would never happen today. No parent would do it and no municipal government would miss the opportunity to jail the parents for endangerment. As a society, we’ve tried to remove risk-taking. It’s like the world is run by insurance adjustors. Maybe it is.

I read a book for my doctoral studies called Antifragile: Things That Gain from Disorder, by Nassim Nicholas Taleb. Taleb argues (in a long and winding tome that desperately needs a good editor) that “the more comfortable you are with looseness and uncertainty, the less fragile your environment is” and that “complex systems are weakened, even killed, when deprived of stressors.”

Taleb rightly claims that current society, with its tall fences and tightly wound structures, is quite fragile.

Malcolm Gladwell wrote the same thing 20 years ago (in a much more engaging way) in an article for New Yorker called “Blowup.” Gladwell’s controlling thesis is that it’s a myth to believe we can manage the error out of complex systems, whether in corporate settings or in personal relationships. His story – the blowup reference in the title – is the O-ring failure that caused the space shuttle Challenger to explode.

When your highest value is failure prevention, one little problem can ruin everything.

The premise of both of these readings is the same premise of innovation. Creative thinking introduces risk, which leads to innovative behaviors, practices, products and services. Innovation is down and out; it’s disruptive. It creates volatility to the status quo, and from that volatility new life emerges. New life cannot, in fact, emerge without this volatility.

But if we can recognize that volatility is essential to new life, why do we continually suppress it? That our fear of failure is greater than our love of gain is known as Prospect Theory. (Here’s why we have a self-defeating tendency to play it safe.) We favor “failure prevention” as our preferred value.


I looked up the history of the term “free range,” or open range, in America. Up through the 1870s everything was wide open. The invention of barbed wire changed that. For about a generation, cattle owners would put up fences wherever they felt like it – regardless if they owned the land or not. There’s a whole history called the Fence Cutting Wars. Federal laws intervened in 1890, and with the rise of the railroad, we began slowly to section off the country.

Now here in my home land in Texas, we have zero lots with 9 foot tall wooden fences so no one can see their neighbor. It’s the stupidest thing ever. When we lived in Tennessee, we were open yard. Our kids would roam all over the neighborhood. We got to know a lot of families that way. Compared to their life in Texas, our kids were free range.

Scripture has a lot to say about this problem.

One day he got into a boat with his disciples, and he said to them, “Let us go across to the other side of the lake.” So they set out, and as they sailed he fell asleep. And a windstorm came down on the lake, and they were filling with water and were in danger. And they went and woke him, saying, “Master, Master, we are perishing!” And he awoke and rebuked the wind and the raging waves, and they ceased, and there was a calm. He said to them, “Where is your faith?” – Luke 8:22-25 ESV

The disciples were afraid of the danger. And who are we to judge them? They were literally drowning. Sure, we want safety, and the reason is that there are real dangers. Yet what does the story tell us? No matter how dangerous life gets, Jesus is in the boat with us, calm to the point of sleeping, heart rate about 60 or so, there to tell us, have faith.

I once had a pastor tell me he wanted only uplifting music for worship. I thought, what about the Psalmist laments? Three years later he had an affair and left the ministry. Like the O-ring disaster, he was built for failure prevention, and eventually, what happened? He blew up.

There is value in affirming pain and loss within the context of a loving community. We try to remove risk, but we can’t. Bad things will happen.

When we focus on safety, we don’t get greater safety. All we get is increased fragility.


Taleb writes (with a typical grain of great insight wrapped around of bunch of poor writing):

Technology is the result of antifragility, exploited by risk-takers in the form of tinkering and trial and error, with nerd-driven design confined to the backstage. Engineers and tinkerers develop things while history books are written by academics; we will have to refine historical interpretations of growth, innovation, and many such things.

No, I wouldn’t let my two sons ride a horse from here to New York, then take a car back. But which approach to parenting is more endangering? Today our kids sit in closed off rooms staring at screens all day while pediatricians and psychologists cry how poorly they are doing.

There’s a movement called “free range parenting.” It’s “the concept of raising children in the spirit of encouraging them to function independently and with little parental supervision.” We are scared to death of letting our kids roam free.

And just as we’ve taken the free range out of our kids, we’ve taken free range out of our faith. We put up all kinds of fences. We want to create an environment in which we don’t have to worry. But is that possible? Or are we just lobotomizing faith itself? All of our rules and boundaries have fragilized the very thing we want to protect. When we lock things down, whether our kids or our faith, we make it fragile.

Growth comes from learning to navigate the free range, not from creating fences.


If we are not honest about risk, loss, lament, pain – danger – we are not honest at all. We need to free range our kids and we need to free range our religion. Hassib Taleb says, “antifragile systems are hurt when they are deprived of their natural variations (mostly thanks to naive intervention).” (p. 91)

Taleb writes that the goal is a third way – not fragility or anti fragility, but a robust approach that can adapt to risk as it arises.

If you want to create an environment that can handle the future well, focus not on safety but on adaptability.

In fact, Fast Company claims that our capability to adapt is the key to the future of work itself.

You’ve got real dangers ahead of you. It doesn’t matter what you’re doing. It’s true. Who knows what will happen next month. You may take on water. But your goal isn’t to worry about the water levels. Instead, have faith – look at Jesus. The Abernathy boys only had a few simple rules for their safety and well being. We have freedom on the open range of life. God just gives us a few rules for own safety.

Danger is part of the package. Life is dangerous. Jesus doesn’t promise us a danger-free life. In fact, he takes us out into dangerous waters. Instead of looking for safety, Jesus invites us to look at him. After a few near death experiences while following Jesus around, we’ll become robust indeed.