Why Not?

A few weeks ago, I published an essay called The Freedom to Ask Why. It was a reflection on a lifelong habit of questioning assumptions and how that habit shaped many of the most important decisions in my life. I wrote about asking questions as a child, challenging inherited beliefs, and discovering that independent thought is something different from either conformity or rebellion.

The response to the essay was deeply encouraging, but one message in particular stayed with me. A longtime friend reached out to tell me how much he connected with the piece. He described growing up with the same need to understand rather than simply accept. Like me, he had never found “because you’re supposed to” to be a satisfying answer. Then, almost as an afterthought, he ended his message with two simple words.

Why not?

He was joking, at least partially. His family was packing up their lives and moving across the country, and he admitted he was feeling a little more “Why the hell not?” than “Why?” at the moment. We laughed about it, but after our conversation ended, I found myself returning to those two words again and again.

Eventually, I realized they weren’t simply the opposite of my previous essay. They were its companion. The Freedom to Ask Why was about questioning inherited beliefs. Why Not? is about questioning inherited limitations. The first asks whether something is true. The second asks whether something is possible. Asking “why” taught me to think for myself. Asking “why not?” taught me to live as though my choices mattered.

Looking back, I can see that this question has quietly accompanied me through every stage of my life.

As a teenager, after Kurt Cobain died, I picked up a guitar. I wasn’t trying to become a rock star. I simply remember thinking that if nobody was making the music I wanted to hear, why not try writing it myself? Whether anyone else ever heard it felt almost secondary. The act of creating was itself an answer to the question.

Years later, when I met the woman who would eventually become my wife, I was rejected more than once. Most people would have interpreted that as the end of the story. I didn’t. Something in me believed the relationship was worth pursuing, and beneath that conviction was a quiet but persistent question: why not keep trying?

The same pattern appeared again when we founded Wellspring Psychology. Conventional wisdom in our profession often says not to go into business with friends or family, and to build your identity around a narrow specialty. Both recommendations exist for good reasons, but neither fully matched my experience. I trusted the people I was building with, and I believed human beings lived across the entire developmental spectrum rather than inside diagnostic silos. Asking “Why not?” eventually helped shape what we now call Therapy for Every Season of Life. That philosophy wasn’t born from a business plan. It grew from repeatedly questioning whether the assumptions our profession had inherited were the only assumptions available to us. They weren’t, at least not for us.

As I reflected on these moments, I began to notice something they all had in common. None of them started with certainty. None of them began with confidence. They began with a willingness to examine a limitation that everyone else seemed to accept and ask whether it was actually real.

That realization didn’t begin in adulthood. Even as a child, I seemed fascinated by where authority ended and reality began. My parents could send me to bed, but they couldn’t make me sleep. They could decide what appeared on my dinner plate, but they couldn’t make me eat it. Looking back, I don’t think I was simply resisting authority. I was beginning to distinguish between actual constraints and perceived constraints.

That distinction has stayed with me ever since. Gravity is an actual constraint. Time is an actual constraint. Mortality is an actual constraint. There are realities that no amount of optimism or determination can erase.

Many of the limitations that shape our daily lives belong to an entirely different category. They are expectations, traditions, policies, habits, cultural norms, and inherited stories. Some are wise. Some deserve to be preserved. Some deserve to be questioned. The mistake is treating every human convention as though it carries the same authority as gravity.

One of the strangest realizations of adulthood is discovering how often we wait for permission from people who cannot actually give us what we are seeking. We wait for permission to write the book, start the business, change careers, charge what our work is worth, create something new, or become the person we quietly hope we might become. We imagine that one more credential, one more promotion, one more conversation, or one more year of preparation will finally make us ready. Although some barriers are external, far more are internal. We construct an invisible committee of imagined authorities and quietly hand them responsibility for decisions that have always belonged to us.

One must give value to their existence by behaving as if one’s very existence were a work of art.

— Friedrich Nietzsche, quoted by Dr. Josh Maddox in "Why Not?"

The pandemic made this visible on a scale I had never witnessed before. Almost overnight, assumptions that had felt unquestionable suddenly became negotiable. For decades, many people had accepted that work required an office, school required a classroom, productivity required physical supervision, and life had to be organized in a particular way. Then reality interrupted the script.

As a psychologist, I found that fascinating. The pandemic wasn’t simply a public health crisis or an economic disruption. It was, in many ways, a global experiment in questioning assumptions. Millions of people suddenly found themselves asking questions they had never seriously considered before. Why do I have to live here? Why do I work these hours? Why do I commute every day? Why can’t I work from somewhere else? Why can’t school look different?

Some people couldn’t wait to return to the old script. Others realized they wanted to write a different one. The point wasn’t that every change was good. Many weren’t. The point was that an event large enough to interrupt our routines also revealed how many of those routines had always been more negotiable than we imagined. For the first time in a long time, millions of people discovered the difference between a genuine constraint and an inherited assumption.

That, I think, is what the question “Why not?” is always trying to uncover.

For years, I interpreted this tendency as a rebellious streak. If someone told me, “Because that’s how it’s done,” I could feel resistance rise almost immediately. I now think that reaction had less to do with authority than with explanation. “Because that’s how it’s done” isn’t an explanation. It’s an appeal to tradition. It asks for compliance before understanding.

The younger version of me often responded with defiance. The older version responds with curiosity. Help me understand. Show me the reasoning. Convince me. If the constraint is real, I’ll gladly respect it. If the tradition contains wisdom, I’ll gladly learn from it. What I no longer want to do is surrender my agency before I’ve examined whether the limitation is actually real.

Over the past several weeks, I’ve come to believe that “Why not?” is really a question about authorship.

For much of our lives, we experience ourselves as characters moving through a story that someone else has written. Our families shape the opening chapters. Our culture provides the setting. Schools, institutions, traditions, and expectations hand us scripts long before we are old enough to question them. Without realizing it, we begin to confuse inheritance with destiny.

Then, gradually, a different realization emerges. The story is not finished. More importantly, no one else is holding the pen.

The question “Why not?” is the moment we stop seeing ourselves as passive characters waiting for the next chapter to unfold and begin recognizing that we are one of the authors of our lives. We cannot rewrite every page that came before us, nor can we control every plot twist that lies ahead. Life will always remain a collaboration between circumstance, chance, other people, and our own choices. Yet we retain something profoundly important: we participate in what comes next.

Years after I had begun thinking this way, I came across a line from Friedrich Nietzsche that stopped me in my tracks: “One must give value to their existence by behaving as if one’s very existence were a work of art.” I remember reading it and thinking, Yes. That’s it.

We are not standing in a gallery admiring a finished painting. We are holding a brush. We don’t control the canvas, the weather, or every color available to us. We don’t paint alone. Other people add strokes. Circumstances alter the composition. Chance introduces unexpected colors. Yet we still participate in what the painting becomes.

That realization transformed my understanding of freedom. In my previous essay, I argued that freedom is conscious participation in the creation of meaning. I still believe that with all my heart. I would simply add one more thought.

Meaning is not only discovered.

Meaning is also created.

Every time we ask “Why not?” we acknowledge that we are not merely inheriting a life. We are helping shape one. We are not simply readers watching the story unfold, nor are we omnipotent authors who control every chapter. We are something both more humble and, in many ways, more hopeful.

We are co-authors.

Perhaps that is the deepest invitation contained within those two simple words.

Not reckless optimism.

Not blind defiance.

Not the denial of reality.

Instead, they invite us to examine whether the boundaries that define our lives are genuine constraints or merely inherited assumptions. They remind us that while we will never control every chapter, we always participate in the next one.

Every meaningful chapter of my life seems to have begun the same way.

Not with certainty.

Not with confidence.

Not with permission.

With a question.

Why not?