“I would not give a fig for the simplicity this side of complexity, but I would give my life for the simplicity on the other side of complexity.”
Oliver Wendell Holmes Jr
Keeping it Simple Doesn’t Work
Most people believe that “keeping it simple” is actually a good thing; however, this isn’t true at all.
Living a simple life is only good if you’ve no ambition, responsibilities or purpose on this planet.
It’s powerful to remember that when we fail to embrace and master the true complexities of life, we’ll find that they have a tendency to master us. Which allows complexities to build up around and on top of us.
We become busy. We stop caring for ourselves. Life takes the wheel and begins to drive.
We are no longer “cause in the matter”; instead, “the matter is now causing us.” We become a victim of our circumstances rather than the hero of our lives.
Do You Remember the Hero Within You? The Right and Wrong Side of Complexity.
The people on the “wrong side of complexity,” the “victim” side, react to the angst of a situation that produces and sustains high levels of busyness, repeat problems and blind spots for them.
Here we unintentionally develop the deep-seated and ineffective intuitions and habits that run our lives.
On the “right side of complexity,” the “hero” side, we not only handle our business, but we intentionally build deep-seated and highly effective intuitions and habits through the use of processes and practices.
It is here that the genesis of the “Habits of Heroes” resides. It is also here where true freedom is found.
Generating the Habits of Heroes
We generate these “habits of heroes” through the meticulous work we do while crossing complexity,
and it is that meticulous work that retools our habits and intuition in ways that support our ability to live a good life.
You see, freedom is the ability to…
…do what you want to do when you want, but most of us are not free because our environment is what has produced our thoughts, desires and even our perceived needs.
Here, in this phase of our work, we’ll shift our thoughts, desires and perceived needs to line up with a life that you and God say is good,
rather than what our culture, or your randomly produced feelings and desires, say is good.
This pathway to pure freedom begins by revealing what has and will continue to control every aspect of your life. Your operating system.
Strategic Writing
When we write, we expand our understanding in ways that produce new thinking—thinking that leads to more powerful distinctions, which allow us to better identify and fulfill the purposes for which we were created.
1: Why doesn’t “Keeping it Simple Stupid” work in a highly competitive environment?
In a highly competitive environment, “Keeping it Simple, Stupid” (KISS) doesn’t work effectively because it often encourages stopping at a superficial level of simplicity, failing to engage with the essential complexities that drive true success. While KISS is valuable for avoiding unnecessary complication, it can be misinterpreted as a mandate to avoid all complexity. This leads to a naive simplicity that ignores the dynamic and multifaceted nature of competitive markets, leaving individuals and organizations vulnerable to disruption and unable to develop the “deep-seated and highly effective intuitions and habits” needed to thrive.
True competitive advantage emerges from embracing and mastering complexity, “crossing complexity.” This involves the “meticulous work” of learning, training, and incorporating intricate details into a new, higher level of simplicity, what Oliver Wendell Holmes Jr. referred to as the “simplicity on the other side of complexity.” This is the essence of Albert Einstein’s advice: “Make things as simple as possible, but no simpler.” It means stripping away superfluous elements, then delving into the inherent complexities, and finally achieving an elegant, profound understanding that makes the previously complex feel simple and manageable.
Ultimately, a rigid adherence to an initial, unexamined KISS prevents this crucial adaptive cycle. In a competitive landscape, those who continuously engage with emerging complexities, integrate them into their operations, and achieve this hard-won simplicity will consistently outperform those who remain stuck in a basic, static understanding. It’s not about avoiding complexity, but about mastering it to unlock true freedom and sustained effectiveness.
Keeping it Simple allows someone to avoid the complexity of a situation. This tends to make the person accept the easy path. The quote by Oliver Wendell Homes describes a very common path for people on this side of complexity In order to become what we were intended then putting yourself through complexity is vital to live what we say is a good life. Viktor Frankel had a quote that is also relevant. “What is to give light must endure burning.” So, living on the other side of complexity will require you to live with complexity to truly find the purpose of what we were create to fulfill.
1: Why doesn’t “Keeping it Simple Stupid” work in a highly competitive environment?
A highly competitive environment is not simple itself, so it is not a good idea to keep things simple, stupid there. There are many important details and contexts, that are not constant. They change, some of them cease to exist, others are built. It is a constantly changed environment. We can use the “Keeping it Simple Stupid” principle in particular simple things (because they are simple itselves), but it is not possible to use it in a highly competitive environment. It doesn’t work, and it is even dangerous to use this principle in a constantly changing environment, because we can miss some important details and contexts in this way very easy.
1: Why doesn’t “Keeping it Simple Stupid” work in a highly competitive environment?
– There are several reasons “keeping it simple” doesn’t work. Our highly competitive environment is a “complex” one and trying to keep things “simple” means we have to ignore or deny the dynamics that impact our lives. It keeps us in a position of reacting to anxiety rather than mastering the processes and practices that shape our intuitions and habits so that we are the cause of outcomes rather than the victim of them.
Q: “Why doesn’t ‘Keeping it Simple Stupid’ work in a highly competitive environment?”
A: I used to believe K.I.S.S. did. It sounded clever. It felt efficient. But the truth is—when the stakes are high and the world keeps moving faster—“keeping it simple” can actually keep me stuck.
Life isn’t simple. Business isn’t simple. People aren’t simple. And neither is the calling I’ve been given. So when I try to oversimplify things that are complex by nature, by habit and conditioning I end up doing just enough to stay afloat—but never enough to truly grow.
In a highly competitive environment, the ones who win are those who’ve done the work to cross the swamp of complexity—to build systems, replace old habits with new ones, and intuition that can navigate and leverage real-world problems with real-world solutions. That’s not simple. That’s strategic.
“K.I.S.S.” might get me started, but it won’t get me to mastery. And it definitely won’t help me stand out in a world where everyone’s fighting for attention, trust, and results.
So I’ve learned that success doesn’t come from dodging complexity—it comes from training and crossing through it, mastering it, and rising above it. That’s where the freedom is. That’s where the power is. And that’s where I’m headed, and intend to live.
1: Why doesn’t “Keeping it Simple Stupid” work in a highly competitive environment? Because my simplicity means not identifying my purpose, not assessing all the parts of life and how they interrelate, and not creating an operating procedure that can produce the outcome I’m looking for. Fulfillment of any noble purpose requires valiant intentionality and disciplined execution. The process can then take me to a higher plane that makes the new normal seem easy. Success creates power which creates easier solutions to future problems.