The Mirage of Perfect Information

FM (Friday Morning) Reflection #29

Ever since I started writing, lecturing, and appearing in public forums, I’ve been asked a familiar question:

"You seem to have a really cool job. How did you get there?"

The answer is both personal and professional, shaped by who I am, where I started, and the choices I made along the way. My career began in media—working across photography, television, and digital content creation. Over time, I became fascinated by how data and emerging technologies could transform business strategy. That curiosity pulled me deeper into analytics, AI, and innovation—fields that not only intrigued me but also provided a way to help companies navigate change.

At each stage, I’ve tried to stay open to new ideas, experiment, and learn what’s next. That mindset—alongside a mix of strategic thinking, hands-on problem-solving, and a willingness to take some leaps—has led me to where I am today, helping shape the future of media and business through AI and technology. But if I’m being honest, I didn’t plan it.

Uncertainty and the Uncomfortable Moments

For every opportunity that worked out, there were moments of doubt, failure, and tough decisions.

In 2001, my role and most of my team were eliminated because the owner of the ad agency I worked at chose not to invest in digital. I’ve worked under leaders who prioritized their own interests above those of the business or their employees. And sometimes, I’ve let my own ego cloud my judgment.

I share this because in retrospect, things often look as if they were certain or intentional—as if we should have seen every sign and anticipated every outcome. But the reality is, we never have perfect information. This is despite the endless number of sources to scroll, explainer videos to watch, searches to do, and people being willing to offer their advice. And we all have biases.

Looking back, I realize that even if I had to make the same decisions over again—knowing only what I did at the time—I’d likely make similar choices. That recognition surfaces a few key insights:

1. We owe ourselves a bit of kindness.
   Despite things not always going our way, we often do the best we can with the resources, knowledge, and circumstances at hand.

2. There is always something to learn.
   Every experience—good or bad—offers a lesson, an insight, or a piece of wisdom that can serve us in the future. Curiosity is a powerful intrinsic motivator, especially when discomfort or uncertainty sets in. When we combine curiosity with empathy and self-awareness, we become better at processing cognitive dissonance—when new information challenges what we thought we knew.

3. We can be generally right but specifically wrong.
   A good principle might not always translate into a perfect decision. Take baking bread: the essential ingredients—flour, water, yeast, and salt—are the same, yet endless variations exist. Small adjustments in process, technique, and environment make all the difference. The same applies to careers, leadership, and life.

4. Experience and competency matter.
   Dreaming big is great, but execution matters. Ambitious goals require hard work, know-how, teamwork, and persistence. The moonshot ideas we celebrate only succeed when paired with rigorous effort and expertise.

5. We all start as complete noobs.
   Whether we stay that way is up to us. Every expert was once a beginner. The willingness to embrace that truth—and embrace the discomfort of learning—separates those who grow from those who stagnate.

Choosing to Learn and Adapt

Many of the pivots I’ve made in my career were driven by curiosity, a desire to tackle a challenge, or the necessity to adapt. It would be easy (and a little self-aggrandizing) to tell others to follow my path. But the truth is, we each have our own path to forge.

What we can do is share what we’ve learned along the way—offering perspectives, insights, and reflections that might help others navigate their own journeys. And in that, we can learn together and hopefully, do good by better.

Have a great weekend!

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Photo Bonus

This is an example of how something becomes obvious in retrospect.

I was walking through Manhattan with my Polaroid camera and happened to look down to see light filtering through the sidewalk grate. I thought the pattern of light and silhouetting of my shoes was interesting and decided to attempt a time exposure while hand-holding the camera. If you’ve ever taken a long-exposure photo you will know that’s hard to do and I anticipated that it would be a throwaway shot.

But as the photo developed, I was in for a complete surprise! Not only did the image come out reasonably well, but it also revealed the presence of a train line below — and which I had not noticed when standing right there above it. I was focused on the pattern of the light coming through the grate and had failed to recognize the tracks hiding in plain sight below — the thing that actually makes this photo interesting.

Taken with my Polaroid SX-70/MiNT SLR 670-X Ming Edition, on Polaroid B&W 600 film.