The Freedom to Ask Why

I have been asking “why” for as long as I can remember.

My parents will tell you that I started early. Every answer seemed to generate another question. Why does that work? Why do we do it that way? Why is that true? Some people found my curiosity charming. Others found it exhausting. A few found it threatening.

One of my earliest memories of this tendency comes from Sunday school. I remember hearing the story of Noah’s Ark and raising my hand with what seemed to me like a perfectly reasonable question.

“If Noah brought two of every animal onto the ark, what about the fish?”

The teacher looked confused.

“Well, fish are animals. Dolphins are animals. Whales are animals. Why weren’t they on the ark too?”

I was not trying to challenge religion. I was not trying to start an argument. I was certainly not trying to make some sophisticated philosophical point. I was a child trying to make sense of a story. The explanation I had been given and my understanding of the world did not quite fit together, and I wanted help reconciling the two.

Looking back, I think that moment captures something fundamental about how I have moved through life. I have never been particularly comfortable accepting ideas simply because they are widely accepted. If something doesn’t make sense to me, I feel compelled to examine it. Not because I assume it is wrong, but because I want to understand whether it is true.

That habit followed me into school. I often struggled with subjects when nobody could explain why they mattered. It wasn’t that I disliked learning. Quite the opposite. I loved learning. What I found difficult was memorizing information without understanding its purpose. If someone could show me how a concept connected to reality, I was all in. If the answer was simply, “Because you need to know it,” my interest quickly faded.

The same pattern showed up in sports, religion, business, politics, and social life. I found myself drawn toward the assumptions that most people seemed to accept without examination. Why do we structure education this way? Why do we define success this way? Why are these social norms treated as self-evident? Why do some ideas become unquestionable while others remain open to debate?

For many years, I described myself as a contrarian. More recently, I have become less convinced that the label fits.

One of the most useful distinctions I have encountered came from the observation that the opposite of conformity is not rebellion. At first glance that sounds wrong, but the more I thought about it, the more sense it made. The conformist accepts an idea because the group accepts it. The rebel rejects an idea because the group accepts it. Both remain psychologically tethered to the crowd. One moves toward consensus and the other moves away from it, but the crowd still determines the direction.

The rebel seeks the edge. The questioner often finds himself there.

— Dr. Josh Maddox, "The Freedom to Ask Why"

Independent thought requires something different. It requires a willingness to examine assumptions without already knowing where you will land. Sometimes that process leads you away from conventional wisdom. Other times it leads you directly back to it. The goal is not agreement or disagreement. The goal is understanding.

This realization helped me make sense of many of the choices I have made throughout my life.

When I entered private practice, I was repeatedly told that specialization was the key to success. Find a niche. Become known for one thing. Focus your efforts. There was certainly logic behind the advice, and I know many people for whom it has worked well. Yet the more I examined the assumption, the more I found myself asking whether it actually reflected the complexity of human beings.

My experience as a psychologist suggested something different. Anxiety affects relationships. Relationships affect identity. Identity affects meaning. Meaning affects purpose. The challenges people face rarely arrive neatly separated into categories. The more I worked with people, the more interconnected everything seemed. That understanding ultimately shaped the way we built our practice. We chose a different path not because we wanted to rebel against conventional wisdom, but because a different model felt more consistent with what we were observing.

The same process occurred when I was told that going into business with friends or family was a terrible idea. Like most conventional wisdom, the advice existed for a reason. Plenty of people have learned that lesson the hard way. Yet I could not help asking whether the rule was universally true or simply generally true. Could trust, shared values, and a long history of mutual respect outweigh the risks? Could relationships be a strength rather than a liability?

Nearly two decades later, I am grateful that I was willing to ask the question.

Questioning assumptions has not always made life easier. It has occasionally put me at odds with institutions, groups, and individuals. It has led some people to see me as difficult, argumentative, rebellious, or contrarian. It has cost me relationships. It has sometimes placed me on the outside looking in.

For a long time, I embraced those labels because they seemed to explain my experience. Today I see things a little differently.

I do not think I became comfortable being an outsider because I wanted to be different. I think I became comfortable being an outsider because asking honest questions often put me there.

That distinction matters.

The rebel seeks the edge. The questioner often finds himself there.

When I look back across my life, I do not see someone trying to oppose convention for its own sake. I see someone who kept asking why long after many people had stopped. Sometimes those questions led me toward conventional wisdom. Other times they led me away from it. In either case, the process itself mattered more than the destination.

What eventually became clear to me is that questioning assumptions was never really about being right. It was about freedom.

For much of my life, freedom meant the ability to do what I wanted. I wanted the freedom to choose my work, spend time with the people I loved, structure my days according to my values, and pursue projects that felt meaningful to me. Like many people, I associated freedom with external circumstances. Financial freedom, professional freedom, and freedom of time all seemed important because they expanded the range of choices available to me.

I still believe those freedoms matter. There is something profoundly valuable about having the ability to shape your life rather than having your life shaped entirely by necessity. Yet as the years passed, I began to notice that another kind of freedom mattered just as much.

Once you acquire enough freedom to do what you want, a different question begins to emerge. What are you still trapped by?

A person can have financial freedom and still be governed by fear. They can have professional success and still be dependent on approval. They can have autonomy and still be controlled by resentment, anger, insecurity, or the expectations of other people. They can possess every external freedom they once dreamed about and still find themselves living according to assumptions they never consciously chose.

Over time, I became increasingly interested in what might be called freedom from. Freedom from inherited expectations. Freedom from identities that no longer fit. Freedom from beliefs that had been absorbed from family, culture, institutions, and social norms without ever being examined. Freedom from the need to control every outcome. Freedom from the assumption that my worth depended upon achievement, productivity, status, or the opinions of others.

Questioning assumptions turned out to be a path toward both forms of freedom. It helped me create a life that felt more aligned with my values, but it also helped me identify many of the invisible structures that had been shaping my decisions from behind the scenes. In many cases, the assumptions that most limited my freedom were not the ones imposed upon me by other people. They were the ones I had unknowingly accepted as my own.

Perhaps this is why I have always felt drawn toward existential philosophy and phenomenology. Both traditions begin with a simple but radical observation: experience comes before explanation. Before there are theories about life, there is life itself. Before there are concepts, there is experience. Before there are stories about who we are, there is the direct experience of being alive.

This does not mean that explanations are unimportant. Explanations help us communicate, organize, and understand our experience. The mistake is believing that our explanations are the experience itself. The map is not the territory. The finger pointing at the moon is not the moon. Our concepts, however useful, are always one step removed from the reality they are attempting to describe.

The more I reflected on this, the more I realized that many of the assumptions I had spent my life questioning were ultimately stories. Some of those stories were helpful. Some were limiting. Some were true. Some were not. Yet all of them stood between direct experience and interpretation. Questioning assumptions created a space in which I could encounter my experience more honestly and decide which stories still deserved a place in my life.

That process, more than anything else, has shaped my understanding of freedom. Freedom is not simply the absence of constraints, nor is it the ability to do whatever we want whenever we want. Freedom is conscious participation in the creation of meaning. It is the willingness to examine the stories we have inherited, to keep those that ring true, to let go of those that do not, and to accept responsibility for the life that emerges from those choices.

When I think about that child in Sunday school asking about fish and whales, I no longer see a future rebel, iconoclast, or contrarian. I see someone trying to understand the world as honestly as he could. In many ways, I have been engaged in the same project ever since. The questions have become larger and the stakes have become higher, but the underlying impulse remains unchanged.

Life presents us with countless assumptions about who we are, what matters, and how we are supposed to live. Some deserve to be carried forward. Others deserve to be questioned. The challenge is learning the difference. For me, that process has always begun with a simple question, one that has shaped nearly every meaningful decision of my life:

Why?