The Conversation I Thought I Had Left Behind

A few months ago, a young member of my family completed his first semester of college.

When we met, I expected the usual conversation about new friends, professors, assignments and what it was like living away from home for the first time.

Instead, he handed me a single sheet of paper and said, “I’ve been thinking about myself.”

On that page were observations about his own behaviour. He had noticed how he avoided things he didn’t feel confident doing, how he sometimes worried more about tomorrow than today, and how easily he sought approval without quite realising it.

There was no dramatic revelation in what he had written. He hadn’t solved anything. He was simply an eighteen-year-old trying, in his own way, to understand why he did what he did.
I began reading it as the reflections of an eighteen-year-old. Somewhere along the way, I stopped reading about him and started recognising myself.
Not in the details. My life at eighteen was very different from his, and the world he is growing up in is different too. But beneath the circumstances were questions I had known for much of my life.

Am I good enough? What if I get this wrong? Should I wait until I feel more confident?

I recognised the voice because I had heard it recently myself.

When I decided to take up sketching, something I had never done before, the thought was not, “I am afraid.” It was much more respectable: “This probably isn’t the right time.”

I almost smiled when I noticed it. I knew that voice.

For much of my adult life, I had assumed that growing older would gradually take me beyond such questions. Looking back, that was one of my quieter misconceptions about maturity. I imagined that experience would eventually replace uncertainty. If I accumulated enough of it through work, relationships, responsibility, successes and mistakes, there would come a point when I would know myself well enough not to be troubled by the same old questions.

Experience certainly changes us. It gives us perspective, teaches us which battles matter and which don’t, and makes us less eager to prove ourselves. Some of the things that once occupied our minds simply stop seeming worth solving.

But experience does not make us immune to being human.

Over the years, I have sat with people at very different stages of life – young professionals trying to find their footing, leaders carrying difficult decisions, parents wondering whether they are getting it right, and people standing at the threshold of retirement. Their circumstances could hardly have been more different, yet some of the conversations underneath were remarkably familiar.

At eighteen, it might be, “Am I good enough?”
Later, it may become, “I need a little more experience.”

With time, it can become harder to recognise because it begins to sound reasonable.

“This isn’t the right time.”
“I need a little more certainty before I decide.”

The words change. Sometimes the conversation becomes better at making its case.

I still recognise those moments in myself: a familiar hesitation before doing something new, a quiet tightening before a difficult conversation, a moment of wondering whether I am equal to what lies ahead.

The surprise is not that these thoughts are still there in my sixties. The surprise is that I once expected them not to be.

I wonder if we place an unreasonable burden on maturity. We imagine that becoming wiser should mean becoming less uncertain, that confidence should eventually replace doubt, and that knowing ourselves should mean no longer being unsettled by ourselves.

But perhaps maturity asks something different.

The same hesitation can appear at very different ages, wearing very different clothes. At one stage it may look like insecurity. Later it may call itself caution. Eventually it may present itself as wisdom.

Sometimes it is wisdom. Sometimes it is simply an old fear that has become better at making its case.

The difficulty is that we cannot always tell the difference immediately. Caution can protect us from a mistake, while fear can disguise itself as caution. And sometimes what feels like fear is simply the discomfort of doing something unfamiliar.

It can be worth asking what the hesitation is protecting us from. Sometimes there is a genuine risk worth considering. Sometimes there is something more personal underneath it – the possibility of failing, being judged, or discovering that we are not quite as ready as we hoped.

Perhaps the more useful response is not to silence the voice, but to become curious about it before deciding whether to follow it.

Years ago, I often mistook the first thought that came into my head for the truth. If I felt uncertain, I assumed I wasn’t ready. If I felt afraid, I took it as a warning to stop. I sometimes gave another person’s judgment more weight than it deserved.

With time, I have learned to pause before giving those thoughts authority.

There is, I have found, a small space between noticing a thought and allowing it to determine what we do.

I have come to value that space more than I value the disappearance of doubt itself.

Doubt may still be there. So may fear, the need for reassurance, and the possibility of getting something wrong. Perhaps these are not unfinished parts of us waiting to be outgrown; they are part of the conversation we carry as we move through life.

When I handed the page back, I thanked him. Not because he had found the answers. He hadn’t.

I thanked him because, without knowing it, he had reminded me of a conversation I thought I had left behind many years ago.

It turns out I hadn’t. I had learned to listen to it differently.