The Viewpoint: The confidence gap – embracing that uncertain feeling

I have sat in a lot of rooms over the course of my career. Boardrooms, client meetings, investment committees, marketing roadshows. Rooms full of people waiting for answers.

For a long time, much longer than I care to admit, I would arrive at those rooms having barely slept the night before. I would spend hours lying awake attempting to predict every possible question, every small gap in my story, every moment where someone sharper than me might spot something I had missed and ask the one question I could not answer. The killer question, as I called it.

Here is the thing nobody tells you early in a career in investment management. Just about everyone else in that room either has done, or is doing, some version of the same thing. Many of us don’t like to admit it, but every now and then someone lets it slip, usually over a coffee or a beer in a more relaxed setting, or occasionally in a performance review: that impostor syndrome still has a voice. There are exceptions of course, but in my experience those exceptions are the ones worth watching most closely.

No doubt

We all know the type. They arrive with certainty already in place. Their macro call is unambiguous, their thesis watertight and their outcome essentially inevitable. They field questions with the easy fluency of someone who has never seriously entertained the possibility of being wrong. They are, in short, impressive, particularly to people who do not yet know enough to notice what is missing. What is missing, usually, is any honest accounting of uncertainty.

What is missing, usually, is any honest accounting of uncertainty.”

Markets are messy, reflective and have a very nasty habit of making you look stupid. Anyone who has spent serious time in this industry knows that the correct answer to most big questions is some version of “probably, but…” or “maybe, but what about….?” The person who skips that second bit is either performing for the room, or they genuinely believe it. One of those is dishonest while the other can be dangerous.

It is probably worth adding one caveat here. Not all outspoken confidence comes from certainty or belief. For some people, including those wrestling with impostor syndrome, decisiveness can be used as a coping mechanism. Talking quickly or forcefully can be their way of staying in the conversation. The volume is not always arrogance. Sometimes it reflects a need to stay relevant in the room.

And yet in the short term, confidence often wins the room. It gets the airtime, the column inches, the speaking slot at the conference. It feels decisive, reassuring, even soothing in moments when uncertainty is least welcome. The market for conviction is enormous, and the supply of genuine intellectual humility is, to put it charitably, quite constrained.

Now for me, for a long time, I thought the anxiety was the problem. The sleepless nights, the relentless prep, the fear of that killer question all felt like a weakness to be managed, evidence that I had not quite earned my place. I no longer believe that, though I cannot honestly remember the precise moment it changed. I suspect it followed one of those casually devastating remarks from my wife, offered without fuss, and understood only later.

I now think the anxiety was doing a job, it was the part of me that understood, before I was willing to admit it, how little control you sometimes have in this business. You are dealing with uncertainty and partial information most of the time and there is no version of that which is entirely comfortable for me. The people who feel that tend to take it seriously. The ones who don’t either have a perfect temperament for the job, which is rare, or they are missing something.

A sense of imposition

Impostor syndrome, that quiet sense that you are one difficult question away from being found out, is not a character flaw. In many cases it is a form of intellectual honesty. It is the awareness that you do not know as much as you would like, that luck plays a role, and that last year’s track record offers no guarantees about this year’s. These instincts are not problems to be fixed. They are tools in your professional toolbox. In this industry, they help anchor judgement, control  overconfidence, and sit quietly at the heart of good risk management.

Now that I have mentioned luck, it is worth staying with it for a moment. The best investors I have encountered share a quality that is surprisingly rare. They can distinguish between what they genuinely got right and when they were simply fortunate. Not in a performative way, but clinically, as part of the way they test their own process. A manager who attributes every good outcome to skill is not just being immodest, they are building a mental model of their own ability that does not leave room for chance. Sooner or later the market has a way of correcting that, usually without much warning.

The most impressive track record is not always the most instructive one. Sometimes it is simply the one that has not yet encountered the kind of market that exposes its weak points. Markets, to their considerable credit, are eventually quite honest about this. The confident thesis that charmed the room in the good years has a way of unravelling quickly, and the people who never doubted themselves are often the least prepared for that moment.

That is why I have learned to pay attention to a different signal.

Always the quiet ones

There is a particular type of person who shows up in investment meetings and says very little for quite a long time. Then they ask one question and the room shifts a little. I have learned to watch for these people. In my experience they are disproportionately likely to be the most genuinely dangerous thinker in the room; dangerous in the best possible sense. They have been listening, building a mental model, testing it silently against what is being said, and waiting until they have something worth contributing. They are not performing. They are just thinking.

The culture of finance, and perhaps professional life more broadly, does not always reward this. It tends to favour fluency, presence and the ability to project certainty in an uncertain world. These are useful skills, up to a point. But the quiet ones who are doing the actual work tend to reveal themselves eventually, not through how they sound in the room, but through what endures once the noise has faded.

The culture of finance… tends to favour fluency, presence and the ability to project certainty in an uncertain world.”

I spent years waiting for the killer question. Preparing for it, occasionally being asked something close to it and feeling the sudden need to slow down and think very carefully before answering. Over time, that sense of threat began to change. Not because the questions got easier, or because uncertainty receded. It never does, and anyone who suggests otherwise is usually simplifying something that should not be simplified.

Volume does not equal value

What changed was the relationship with that uncertainty. The anxiety did not disappear, but it shifted. I worried less about being exposed, more about being ready. Less about finding the perfect answer, more about being clear on the thinking behind it. The killer question was never really about being found out. It was about being willing to be clear about what I know, honest about what I don’t, and disciplined enough to explain why I still hold a view in spite of that uncertainty.

That shift, from dreading uncertainty to working with it, is the closest thing I have found to a durable professional edge. It does not make you the loudest person in the room and it rarely makes you the most immediately impressive.

But it compounds quietly and reliably over time. The kind of thing that doesn’t feel like much, right up until it does.

For professional investors only. This material is not suitable for a retail audience. Capital at risk. This is a financial promotion and is not investment advice. Past performance is not a guide to future performance. Reference to any security is for information purposes only and should not be considered a recommendation to buy or sell.

The value of investments and any income from them may go down as well as up and is not guaranteed. Investors may not get back the amount invested. Portfolio characteristics and holdings are subject to change without notice. The views expressed are those of the author at the date of publication unless otherwise indicated, which are subject to change. Forward looking statements are subject to certain risks and uncertainties. Actual outcomes may be materially different from those expressed or implied.