A founder's confidence: between vision and impostor syndrome

At ten in the morning he stood in front of twenty people and calmly explained why, within three years, their product would change the market. He spoke without notes, answered questions, made a joke. At three the next morning he lay awake, turning the same sentence over in his head: “When will they find out I have no idea what I’m doing?”

Both scenes are real, and both belong to the same person. When founders talk about this, they often add: “But that’s probably normal, isn’t it?” Partly, it is. Creating something out of nothing takes a kind of confidence most people don’t have — and at the same time it triggers, every single day, a kind of doubt most people never experience. A founder has to sell others a conviction that they themselves can sometimes barely hold upright.

In this post I want to write about the confidence of people who build companies: about the optimism this path needs, the doubt that comes with it, impostor syndrome, and its less noticed twin — overconfidence. And about why the two extremes are often two sides of the same coin.

Two truths in one head

Most people imagine confidence as a scale: some people have a lot, others have little. With founders, that picture doesn’t work. The same person can feel invincible and feel like a fraud about to be exposed within a single week. Often within a single day.

This is not a sign that something is wrong with them. It is a sign that their confidence hangs on something that keeps changing: the last meeting, the last figure, the last response from an investor. When things go well, it rises. When things go badly, it falls. And because good and bad days in a company alternate quickly, the founder is riding a lift they do not operate.

I wrote in more detail about the difference between self-image, self-worth and self-confidence in Self-image, self-worth, self-confidence: how they differ and how each is built. For this post, one idea matters: trust in your abilities and a sense of your own worth are not the same thing. The first can legitimately change with events. The second ought to be more stable — but for many founders, it isn’t.

The optimism entrepreneurship needs

Let’s start with what is good about founders’ confidence. Without a certain amount of unreasonable optimism, there would hardly be any companies. Who would leave a secure job and put their savings and years of work into something that statistically often fails, if they were aware of every possibility of failure all the time?

In the late 1980s the researchers Arnold Cooper, Carolyn Woo and William Dunkelberg asked almost three thousand American entrepreneurs how they rated their own company’s chances of success. The result became one of the most frequently quoted findings in the psychology of entrepreneurship: 81 per cent rated their chances at seven out of ten or better, and a third were convinced their chance of success was ten out of ten — in other words, that failure was not possible at all. When asked about the chances of other, similar businesses, they were considerably more cautious.

This is not just naivety. Optimism helps you persevere when things are hard, it attracts colleagues and investors who sense your conviction, and it gives you the energy for the hundreds of small rejections every beginning brings. Psychology also has the concept of self-efficacy — the belief that you can achieve what you set out to do — which is linked to greater persistence. A founder who soberly counted every reason they would fail each morning would probably not persist long enough to find out whether they would.

When optimism turns into blindness

The same optimism that carries a founder through the first years can later blind them. The psychologists Daniel Kahneman and Dan Lovallo described the difference between the “inside” and the “outside” view. When we judge our own project, we look from the inside: we know our plan, our commitment, our abilities — and so we underestimate how often similar projects fail. The outside view would ask a different question: what happened to others who tried something similar?

In a laboratory experiment, Colin Camerer and Dan Lovallo showed that people enter a competition more often when the outcome depends on their skill than when it depends on chance — even when the maths would advise them to stay out. Everyone believes they are above average. They called this reference group neglect: we do not stop to think that we are competing with people who are just as sure of themselves.

In founders, overconfidence rarely shows up as loud boasting. More often it shows up quietly: when you don’t hear the co-founder warning that the money is running out; when you experience every criticism as proof that others “don’t understand the vision”; when you won’t ask for advice because that would mean admitting you don’t know. And often it is others who pay the price — employees who trusted you, a family that remortgaged the house. I wrote about why real confidence is not the same as loudness in Confidence isn’t volume: what trusting yourself really means.

Impostor syndrome: when success doesn’t convince

On the other side is an experience many founders know, even though they rarely talk about it: the feeling that they achieved their success by luck, by performing well, or because people have not yet looked closely enough. In 1978 the psychologists Pauline Clance and Suzanne Imes described it in successful women and called it the impostor phenomenon. It later turned out that people of both sexes and in a wide range of professions experience it. You will find a short explanation in the knowledge base under impostor syndrome, and I wrote about it in more detail in Impostor syndrome: why successful people doubt themselves.

In founders, impostor syndrome takes a particular form. A founder often does work they were never formally trained for: today a managing director, tomorrow head of HR, the day after a finance officer. Nobody appointed them, nobody assesses them except the market. And because they have to show investors and the team more conviction than they feel, the gap between outer performance and inner experience grows. The more successfully the company develops, the wider the gap — and the greater the fear that one day it will be exposed.

The paradox is that success does not calm this fear. People with impostor syndrome often attribute success to external circumstances and failure to themselves. Each new achievement therefore does not become proof of ability, but a new ledge from which they could fall. Often the one responsible is the inner critic — the voice that finds, with every success, a reason why it doesn’t really count.

Fragile and stable confidence

The psychologist Michael Kernis proposed a distinction that is very useful for founders: self-esteem is not only high or low, but also fragile or secure. Fragile self-esteem can be very high, but it depends on external validation, swings strongly with successes and failures, and has to be constantly defended. Secure self-esteem may be more modest, but it does not need daily proof and can take criticism without collapsing.

This distinction explains something that seems strange at first sight: why inflation and impostor syndrome alternate in the same person. Both come from the same fragility. Inflated confidence is often a defence against doubt — if you don’t let it near, you don’t have to feel it. When the defence gives way, the doubt returns with full force. In therapy we don’t talk about such defence mechanisms as mistakes, but as the ways a person once protected themselves.

Where it comes from

When I explore with people where their relationship to their own worth comes from, we often arrive at similar stories. A child who was noticed only when they achieved something exceptional. A child who had to be “good and clever” so as not to burden their parents further. A child whose achievements mattered more to their parents than how they felt. Children like these often learn that love has to be earned — and as adults they sometimes become very successful precisely because that old need drives them.

Entrepreneurship is an almost perfect stage for this pattern. It offers endless opportunities to prove yourself and, at the same time, endless opportunities to fall. The company becomes an extension of the self; its identity merges with the founder’s. When the company grows, the founder is worth something. When the company suffers, it feels as if their worth is suffering.

Shame matters here too. Guilt says “I made a mistake”; shame says “I am a mistake”. A founder who experiences every business blow as an exposure of their worthlessness cannot simply analyse what went wrong — it hurts too much. So they retreat into one of the extremes: into inflation that won’t admit the mistake, or into self-flagellation that turns it into proof.

A conversation that is hard to have

This dynamic often shows most clearly in the relationship with a co-founder or a partner — the people who see the founder up close. Such a conversation might sound like this (a composite, not a real person):

“Every time I open the numbers, you brush me off. As if I’m the problem.”
“Because I know where we’re going. You only see the next three months.”
“Maybe. But when I listen to you, I get the feeling you can’t afford to be wrong.”
(a long pause)
“If I’m wrong about this, I’m wrong about everything. Then I’ve dragged people into something I can’t manage.”
“You didn’t drag us. We came because we wanted to. And you can be wrong about this and still be right about plenty of other things.”

Something happens in this conversation: behind the confident claim “I know where we’re going”, the fear appears that one mistake would expose everything. Once that fear is spoken, the conversation can move away from who is right and towards what is actually happening with the company. This is not only a business shift. It is a shift from defence to contact.

Exercise: an outside view of your own doubt

This exercise combines two things I have written about: the outside view, which helps with excessive optimism, and a kinder relationship with yourself, which helps with impostor syndrome. It takes about fifteen minutes.

1. Write down one decision that is troubling you this week. Not all of them — one. For example: “Should I hire two more people?”
2. Write down what your inner voice says about it. If it is “of course, it’ll work out”, write that. If it is “you have no idea what you’re doing”, write that. Don’t correct it.
3. Change chairs. Imagine that another founder you respect presents you with the same decision. What would you ask them? What would you tell them about the options they have?
4. Write down one thing you would need to make the decision easier. A piece of data, a conversation, advice from someone who has done it before. Then take one step in that direction.
5. Finally, answer the question: “If this decision turns out to be wrong, what will it say about me?” If the answer is “that I’m incompetent” or “nothing”, write down what you would say to a friend who said the same.

If you would like a similar exercise for the inner critic, the knowledge base describes the two columns for the inner critic exercise.

Where this view falls short

I want to be careful here, because a psychological explanation can easily be misused.

Not every doubt is a symptom. Sometimes a founder doubts because the reasons for doubt are real: the product isn’t finding buyers, the money really is running out, the team really can’t cope. If you explain every doubt away as impostor syndrome, you may silence the very signal that should be stopping you. Healthy confidence does not mean never doubting; it means being able to look at doubt and weigh it.

Not every big vision is overconfidence. Some ideas seem unrealistic until they come true. Psychology cannot tell in advance which founder will be right. What it can do is help a person not to tie their worth to whether they turn out to be right.

Not everything is psychology. The market, timing, luck and money decide a company’s success at least as much as the founder’s inner stance. Therapy won’t tell you whether to accept an investor’s offer. It can, however, help you make decisions from a clearer inner place.

And one more important limit: if periods of exceptional confidence, when you barely need sleep, your thoughts race and you make risky decisions you later regret, alternate with periods of deep low mood, talk to your GP or a psychiatrist. Swings like these can be a sign of a mood disorder that needs professional treatment — and that can be managed well.

When your worth equals the company’s worth

The hardest moment for fragile confidence comes when the company fails. That is when it becomes clear how far the founder’s worth had merged with the company. People who built their sense of worth elsewhere too — in relationships, in their bodies, in things they do with no outcome attached — find it hard, but they do get back up after failure. Those who invested everything in a single source of validation often go through a collapse that goes beyond the business loss. I will write about this in A company’s failure is not your failure: how to separate yourself from the business, and about confidence after failure in general in Confidence after failure: how to get back up when things don’t work out.

The way to more stable confidence does not go through more success. It goes through starting to separate your worth from your results. One path is self-compassion — a way of relating to yourself that Kristin Neff’s research links to greater resilience after failure, not to lower motivation, which ambitious people often fear. I wrote more about this in Self-compassion instead of self-criticism: what Kristin Neff’s research shows.

Another path is exploring where the need to always succeed comes from. In relational family therapy, in which I am training, we often see that such a need takes shape in the family — and that it can be understood once you look at it in the context of the relationships it grew out of. The inner critic is often a voice a person once heard from outside; more on that in The inner critic: where the voice that constantly judges you comes from. My sessions take place in person in Ljubljana, and I also work with English-speaking clients.

What to remember

• In founders, optimism and doubt often alternate in the same head — this is common, but it does not mean it is stable.
• Optimism helps entrepreneurship, but it can overshadow the outside view: what happened to others who tried something similar.
• Impostor syndrome and inflated confidence are often two sides of the same fragility — a worth that depends on success.
• Not every doubt is a symptom. Sometimes doubt is a justified signal worth listening to.
• Secure confidence does not grow from more success, but from a worth that is not for sale — one that does not depend on the latest figure in the report.