When Have You Ever Been Creative?

This was the question I faced one day at lunch. I was with a woman who ran her own business and had a vision for it that I admired. She was full of energy, and I could see the potential in what she wanted to build. But then she asked me this question, and I wondered if she did not get it at all.

Our conversation that day had led her to this question because we were discussing what I wanted to do next in my career. I said I was not interested in going back into a role I had already done. I felt I was moving toward something more creative. Her question, “When have you ever been creative?” took me aback. It felt like an insult.

She had known me for a few years. We had met several times but never very seriously. That day at lunch, we had talked about markets, about ideas, about the shape of things. And yet in that moment I realized she had only ever seen the version of me that showed up to work. She had seen my career from a LinkedIn profile. The firms I worked for, the businesses I helped build, the university I attended, and the professional credentials I had obtained. But she had never been given much reason to look further. That was partly on me.

She did not know about the book I had been working on. She probably did not think about the investor letters and research reports I had written throughout my career. Were those not creative? She probably did not see the act of preparing the body for an endurance event as creative work either. She had no way to know about the photography work that had moved from hobby into something more. Contests I had won. A series of images that landed in commercial publications because I wanted to see if I could do it. She did not know any of it because I had never offered it.

It is true I cannot sing. Or act. Or paint. Or draw. Or play a musical instrument. But even that is not quite true. I sing all the time. I enjoy banging on the drums. I can act and paint and draw. No one would ever pay me to do any of those things, but is that limit where the boundaries of creativity begin? Is payment the threshold? Is professional recognition the entry requirement?

I was triggered for a moment, but it passed quickly. Not long after that lunch, my daughter commented one day about her own lack of creativity. She was expressing the difficulty of writing a story in English class. I pressed her. Do you think you are creative? She said not really. So now the same question had arrived twice within a short period of time, from two different directions. That felt like something worth paying attention to.

I did not like my daughter’s self-characterization. It felt limiting without really examining the truth. So I asked my daughter to play a little game with me. I said, you love reading all those books about dragons and vampires, and you love Harry Potter. I want you to close your eyes and think of a character that is unique to your mind. What is it? Is it human? Is it alien? Is it mystical? Where is it from?

She answered all these questions. The character was a combination of the influences she was drawn toward, but it was unique to her mind. So where does it live? Is it alone there? What does it do?

Now think of something that happens to it. Is that event dangerous? Exciting? Life changing? We were on a long drive, so I kept this going for a while. By the end, she had created an entire universe and an entire story that was unique to her. It may have even made for a pretty good short story. When we got to the barn, I asked her one more simple question.

Kendall, are you creative or not?

As one might expect of a 16-year-old, she did not say a word, got out of the car, and went to see her horse. Dad 1, Kid 0.

But here is what I know. My daughter is creative, and I had her demonstrate it to me and to herself. If I had been in that car with the woman from lunch, the same exercise would have worked on her. Close your eyes. Think about the business you are building. What does it look like in ten years that is different from today? Who is there who is not there now? What problem does it solve that no one has named yet? What do you need to do to bring that vision into focus? What architecture do you need to build to make it real?

That is not only strategy. That is imagination. That is creativity operating in a domain she trusted. She just did not see it that way yet.

There is an irony I have noticed. Many people who are drawn to creativity spend a long time reading about it before they give themselves permission to do it. They finish one book and move to the next, collecting frameworks and methods and permission structures, as if the next chapter will be the one that finally unlocks something. Creativity does not come from reading another book. It arrives in the moment you stop waiting for the conditions to be right and start anyway. Badly, slowly, and uncertainly. The discomfort of that is not a signal that you are not creative. It is often the signal that you are.

We are all creative. We can all perform or create or build. Some can do so better than others. But the more honest question is how long you have worked at it. Creativity is not a fixed trait distributed at birth. It is a capacity that responds to pressure, repetition, and time. It is like any other form of endurance. It requires training the creative muscles. The people who seem most creative are usually just the ones who kept going when it felt uncomfortable or unnatural or amateur.

I have moved toward something more creative in my career. There are these essays on Wondering Aloud. There is a forthcoming book. There is a body of work building around it. Those things exist because I kept asking questions and refused to stop when the answers were uncertain. That is what creativity requires. Of course, I hope it all becomes commercially viable, but commercial viability is not what will define whether it was creative.

Maybe that is why I have become so interested in the difference between constraints and limits. I believe in the constraints that allow creativity to become possible. I do not believe in limits. Limits are what get created when we misjudge reality. The biggest misjudgment may be believing you need to become something you already are.

Thank you for reading Wondering Aloud.

Steve Barth, CFA

Wondering Macro LLC