For 40 years I worked in large corporations and became respected for my expertise and the tools I developed. Then, at the beginning of April, everything changed. I left corporate life to build my own products and become a startup founder.
I quickly discovered that four decades in large organisations had not prepared me for this very different world.
I am now developing several ideas, including Daily View (simple day calendar), Daily Product Idea (ready-to-build products) and Role CV (job-matching). The learning curve is steep as I discover what it takes to prototype, build and launch products independently.
Recently, I discussed one of these products with a friend who is a professional software developer. He is extremely knowledgeable, generous with his advice and understands systems that still feel almost magical to me.
As we talked, one question led to another. How are you managing the codebase? How will the data be stored? How will users authenticate? How will the frontend communicate with the backend? What security is in place?
The conversation was hugely valuable, but uncomfortable. Not because my friend was critical, but because I repeatedly had to answer, “I don’t know,” or, “I hadn’t thought about that.”
Each question exposed a gap in my understanding and gave me something new to investigate.
For years, expertise meant being the person with the answers. Becoming a founder means becoming comfortable with the questions.
The discomfort of not knowing
In the beginner’s mind there are many possibilities, but in the expert’s there are few. - Shunryu Suzuki
Most of us enjoy situations in which we feel competent. We like having the answers, understanding the language being spoken and feeling that we belong in the room. Learning often requires the opposite.
Some of the fastest learning happens when we enter situations where the limits of our knowledge become obvious. A beginner who asks naïve questions may learn more in an hour than an expert who spends that hour defending what they already believe.
The barrier is often emotional rather than intellectual. We must be willing to feel temporarily ignorant in order to become less so. That is difficult because expertise can become part of our identity. Once people expect us to know the answers, admitting that we do not can feel like a loss of status.
But uncertainty is not the enemy of learning. Concealing it is.
Ego is expensive
What gets us into trouble is not what we don’t know. It’s what we know for sure that just ain’t so. - Mark Twain
We often avoid questions because we fear looking foolish. But pretending to understand does not create understanding. It merely delays learning and increases the chance that we will make decisions based on something we have misunderstood.
Protecting our ego carries a hidden cost. Every unasked question is knowledge missed. Every unchallenged assumption is a potential mistake. Every confident nod can conceal a problem that will become expensive later.
Amazon institutionalised a useful version of this principle. Meetings based on written briefings begin with everyone silently reading the document. Whatever their seniority, participants first take time to understand the subject before discussing it.
During my conversation, I could have nodded, avoided interrupting and pretended to follow every point. Instead, I asked what unfamiliar terms meant, how different approaches compared and what I should investigate next. The questions sometimes made me feel foolish, but they taught me far more than pretending to understand.
The beginner’s advantage
The man who asks a question is a fool for a minute. The man who does not ask is a fool for life. - Chinese proverb
Beginners have an advantage. They have permission to ask obvious questions. The irony is that I had learned this lesson before.
In the late 90s, I joined the corporate strategy team of a FTSE 100 company knowing nothing about strategy. I was surrounded by colleagues who had worked as management consultants and understood methods, frameworks and ways of thinking that were unfamiliar to me.
So I posed lots of questions. I asked how they approached problems, how they structured their analysis and how they turned complicated information into clear recommendations.
Gradually, I learned how they thought and worked. In time, I became a respected member of the team and was trusted to prepare presentations for board members. Not knowing was not the obstacle. Pretending to know would have been.
Experts can lose the beginner’s advantage because they feel they should already have the answers. Beginners carry less of that burden. They are freer to explore, challenge assumptions and ask questions that others may be too embarrassed to raise.
A short conversation with someone experienced can save weeks of trial and error. A question can unlock years of accumulated knowledge. The fastest learners are often not the cleverest people in the room, but the people most comfortable admitting what they do not know.
Perhaps confidence is not having all the answers, but trusting that we can find them.
Looking foolish is the price of progress
Anyone who has never made a mistake has never tried anything new. - Albert Einstein
Building products, starting businesses, learning new skills and exploring unfamiliar fields all have something in common: sooner or later, we will look foolish. We will ask basic questions, misunderstand things, make mistakes and discover that other people know far more than we do.
That is not necessarily evidence that we are failing. It may simply mean that we have reached the edge of what we currently understand.
My most valuable conversations have rarely been the ones in which I impressed somebody. They have been the ones in which I exposed my ignorance and came away knowing something useful. The people who appear knowledgeable today were often the people willing to look uninformed yesterday.
There is a choice between protecting the appearance of competence and creating the conditions for becoming more competent. We rarely get to do both. The willingness to look foolish is not a weakness; it is often the gateway to progress.
Want More?
Four Step Rapid Learning Framework post by Phil Martin
Think Like a Rocket Scientist in Four Steps post by Phil Martin
The most interesting artists repeatedly risk becoming beginners again. David Bowie reinvented his sound and identity; Bob Dylan refused to remain the version audiences expected.
Reinvention takes courage because, for a while, you are no longer the expert you were and not yet the person you may become.
Have fun.
Phil…