Is Your Experience an Asset or Liability?

Last week, as I spent a weekend morning finishing up work at a crowded Starbucks, a random woman approached and asked if she could grab the other end of my table.

I obliged.

I learned that she studied Art History and worked in art advisory; I had yet to meet anyone who had ever evaluated art and I was immediately curious.

The problem? I didn’t know the first thing about art.

I panicked.

Would she think I was uncultured? Apathetic? Did I need to brainstorm creative questions that would let her know that I somehow know what Picasso and pointillism was?

A piece of art I definitely could not name

As my mind raced around new ways to fake this conversation, the futility became more clear — I had no idea what a good or bad question was when it came to evaluating art.

Every time I began to open my mouth, I realized I couldn’t offer even a snippet of valuable contribution.

Would it impress her that I had seen pictures of the “Renwick Gallery” in my Instagram feed? Would it impress her that I watched “How I Met Your Mother” and saw Lily embark on a fictional career as an art connoisseur in Italy? Would she care that I went to the Louvre in 7th grade and saw the Mona Lisa?

I finally surrendered and admitted the truth about my ignorance. To my relief, she laughed.

Nobody knows about it, it’s okay.”

It was the perfect opportunity — I put my naiveté on full display and rattled off everything I never knew: What does a valuable painting look like? How is oil valued as opposed to other mediums? How is history taken into consideration? Why is Jackson Pollack so damn famous?

She took every question in stride and supported my curiosity through understandable, stupid and even the patently absurd questions.

I became gradually comfortable in this environment — Knowing little meant that I had no reason to fear how a question would be perceived.

As I began to reflect on how much I learned that day about the intricacies of evaluating fine art, I realized that my knowledge came less from strategizing my questions to sound impressive and more from the subconscious — questions I already knew were dumb.

When applying it to a workplace setting, it makes sense — the more experience we have in a specific domain, the more we begin to stake our reputation on this experience.

We worry about imposter syndrome, constantly finding ways to rationalize areas of success for fear of being exposed.

We want to seem conversational, sound aware, and even somehow convince ourselves that our years of experience should lead to nothing less than full confidence.

Despite this, there’s a certain feeling of comfort that comes with knowing absolutely nothing and admitting it. I had no qualms about my lack of intelligence and experience — in fact, I saw it as the impetus that drove learning. At what point does this lack of naïveté become a liability?

In his book, Hacking Leadership, Mike Myatt explores the concept of unlearning — unpacking false truths as real. He questions whether intellect is an asset or liability. In a Forbes piece arguing for the brilliance of naiveté, Myatt writes:

Is it true that the best leaders spend their time talking about, thinking about, and learning about what they don’t know?

Think about this:

  • When’s the last time you asked a stupid question?
  • When’s the last time you asked “what if” instead of immediately shutting down an idea you knew nothing about?
  • When’s the last time you held a candid openness to an approach that bordered on naiveté instead of a proverbial mental fence driven by fear?
  • Do you regularly confuse ego with intellect?

Think years ago about the criticism Mark Zuckerberg received when he pledged to donate $45 billion dollars from Facebook shares in an open letter to his daughter. In the letter, he wrote:

Our hopes for your generation focus on two ideas: advancing human potential and promoting equality.

Much of the criticism stemmed from the fact that he was solving a problem that had no immediate solution — he was too optimistic and naïve to believe equality and potential could be measured, solved, or even somehow move the needle in today’s society.

I was in the camp that immediately snapped that the entire idea was ridiculous. Within two minutes, every logical part of my brain had kicked the idea to the curb.

I wished I was in the initial camp that wondered: “What If?”

Maybe it’s worth it for us to get into areas where we have nobody to impress — where we can receive a deluge of new knowledge without worrying if it contradicts our old.

Of course, there is no one answer to this benefit. Scaling startups do need experience and anecdotal wisdom, after all — but it all comes down to whether this experience is moving your vision forward or stopping your vision from realizing its full potential.

In 2019, I joined the Tradecraft program in an effort to learn more about the world of growth. There was a certain comfort in asking questions about growth concepts that one might never dare to ask or wonder after years in growth.

Growth marketing is a moving target after all — and some of the best ways to move ahead in a world where Google and Facebook are changing their algorithms every day — is simply not to let your experience stunt your desire to continue feeling like there is less to learn.

I’m a Product and Growth Enthusiast based out of San Francisco and currently studying growth marketing out of Tradecraft with interests rooted in building products and empowering technologists to find the best tools to optimize growth. I share insights around Product and careers frequently on Medium or on Twitter at @kushaanshah. All opinions are my own.

Growth @Livongo • Bostonian • Fan of sports and quirky theatre • Marketing Nerd • Weekly reads ✍️

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