When Experience Becomes Certainty

One of the unexpected gifts of this stage of life has been becoming a beginner again.

After spending more than four decades in leadership, much of my professional life had come to feel familiar. Decisions came more easily, patterns revealed themselves more quickly, and uncertainty visited less often than it once had. That confidence had been earned over many years, and it served me well. I rarely stopped to wonder what ways of seeing that confidence might also have been quietly reinforcing.

Retirement changed that in ways I had not anticipated.

Over the past two years, I have found myself learning things that I once had little reason to learn – coaching, sketching, the game of Go, even conversational Marathi. None came naturally. Each reminded me how unfamiliar it feels to start from the beginning after spending much of one’s professional life being expected to know the answers.

Somewhere along the way, I began noticing a habit that had probably been with me for years.

Like most people, I form impressions quickly. I meet someone for a few minutes and instinctively begin filling in the blanks. I hear an opinion and quietly decide how much weight it deserves. I encounter an unfamiliar situation and compare it with something I already know.

These mental shortcuts are not flaws. They help us make sense of a world far too complex to analyse from first principles every day. They are usually the beginning of understanding, not the end of it.

The trouble begins when our first conclusion quietly becomes our final one.

Over time, I have found myself wondering whether these shortcuts sometimes become something more.

Curiosity doesn’t ask us to abandon first impressions. It asks us to delay our conclusions long enough for another possibility to emerge.

Many years ago, I came across a story about Sam Walton, the founder of Walmart. Already one of the most successful business leaders in the world, he was having breakfast in a small neighbourhood diner when another local businessman walked in. Walton turned to his companion and remarked that he admired the man and still had much to learn from him.

The man was not another retail executive or a celebrated entrepreneur. He had built a successful poultry business.

What has stayed with me over the years is not simply Walton’s humility, although that would have been remarkable enough. It was the quiet curiosity behind the remark. Success had not seemed to convince him that learning flowed only from people who looked successful by conventional measures. He appeared remarkably free from the need to decide someone’s value before discovering what they might teach us.

That story stayed with me because it exposed an assumption I had never consciously examined.

How many opportunities to learn disappear before they have a chance to appear – not because people have nothing to teach us, but because we quietly decide, within seconds, who is worth listening to?

Looking back, I cannot honestly say I always approached people that way.

There were occasions when I gave greater weight to an opinion because it came from someone senior or more experienced. Equally, there were probably times when I dismissed an idea too quickly because it came from someone younger, less experienced or outside my own field.

None of this happened consciously. Experience teaches us to recognise patterns, and much of leadership depends on that ability.

Yet I have increasingly wondered whether the same strength carries a quiet cost. The faster we become at recognising patterns, the easier it becomes to mistake a first impression for a complete understanding.

Retirement has quietly unsettled that certainty.

Some of the most meaningful conversations I have had over the past two years have been with people whose experiences bear little resemblance to my own. I have found myself learning from cleints whose questions have stayed with me long after our conversations ended. More than once, I have entered a coaching conversation expecting to contribute my experience and left reflecting on something a client had helped me understand instead.

The more I noticed these moments, the more I found myself wondering whether curiosity begins where certainty ends.

Another realisation arrived more slowly.

The habits of mind we practise with others rarely remain confined to others. It should perhaps not have surprised me that the same certainty I occasionally brought to evaluating people also found its way into how I evaluated myself.

When I began learning coaching, I often caught myself thinking I should already be asking better questions. Picking up a pencil again after many years, I instinctively compared my sketches with the work of people who had practised for decades.

Learning Marathi has become an ongoing lesson in making mistakes publicly and discovering that the world continues quite happily despite them.

I still remember standing outside a neighbourhood shop, searching for an ordinary word I knew I had practised many times. It refused to arrive. We both smiled, stumbled through the conversation, and somehow understood each other anyway.

I had been far more concerned about getting it right than the other person ever was.

None of these experiences asked me to prove myself. They asked for something much quieter: the willingness to remain a learner.

Gradually, I have come to suspect that what keeps us from growing is rarely a lack of knowledge or ability. More often, growth slows when we become too certain – too certain that we understand another person, that we know how something will unfold, or that we know who we ourselves are.

Perhaps that is one of the quieter privileges of growing older.

Experience gives us confidence, but life continues to offer gentle reminders that confidence and certainty are not quite the same thing. One helps us move forward. The other can quietly close doors before we even realise they were there.

Whether I am meeting another person, learning something unfamiliar, or simply noticing my own shortcomings, I have found it increasingly helpful to leave a little more space between what I first conclude and what may actually be true.

I don’t always succeed. First impressions still arrive uninvited.

I have become a little less willing to mistake them for the whole story.