Why Imposter Syndrome Appears at the Peak of Your Career
Why high-achieving founders doubt themselves at their most pivotal moments and how to lead with quiet confidence
Imposter syndrome is often portrayed as something that troubles people at the beginning of their careers, when they are still finding their feet and proving their worth. Yet in my work with founders and business owners, I see the opposite. The most significant wave of self-doubt often arrives not at the start, but at the peak; at the moment when your decisions carry the most weight, when legacy becomes real, and when others look to you as the person who holds the answers.
And I know this feeling personally. I have spent decades leading, advising, navigating change, and guiding high-stakes transitions. I am a high-achieving founder myself, yet when I was recently invited to speak on succession dynamics to a network of construction family businesses, my first reaction was not confidence. It was a quiet internal question:
Why me? … Am I really the person for this?
This is where the School of Life perspective becomes so helpful. The book explains that we often assume those in prestigious roles feel calm, assured, and superior. We imagine an inner world of clarity and composure. Yet their inner lives are as anxious, contradictory, and unpolished as our own. Founder or CEO, successor or chairperson, we all have moments where we feel uncertain.
The book puts it plainly; other people are not as psychologically tidy as they appear. We compare our own private worries, doubts, and tangled thoughts with the calm surface we project onto them. It is an unfair comparison. We see ourselves in full colour and everyone else in an edited snapshot.
At the peak of your career, this tension becomes sharper. You carry years of responsibility, experience, and influence. You understand the stakes. You know how much your decisions affect others. And when you approach a new chapter (such as preparing a business for sale, stepping back from day-to-day leadership, or guiding the next generation), you become acutely aware of the psychological complexity involved.
It is at these pivotal moments that founders have the same doubts:
What if I do this part wrong?
What if my judgment is flawed now, at the most important stage?
What if the business is too dependent on me?
What if others expect more than I can deliver?
What if the next chapter exposes gaps I have always carried quietly?
These are not signs of inadequacy. They are signs of depth. As the School of Life reminds us, maturity is often paired with humility. We recognise our limits. We see our vulnerabilities more clearly than we did when we were younger. It gives us awareness, but it also gives us doubt.
The truth is simple; you feel imposter syndrome at the peak of your career because the chapter you are entering matters. You understand the consequences. You see the emotional weight. You care about doing it well.
In my own work, this is what keeps me steady and confident, even when those internal questions arise:
I return to the reality that everyone, regardless of title, is as human as I am.
They have the same anxieties, private thoughts, and internal contradictions. The “elite founder mind” does not exist, sorry Elon. What exists are people who have taken responsibility, learned to live with uncertainty, and kept going.
Quiet confidence comes from remembering this. Confidence does not mean feeling certain. It means staying grounded when uncertainty shows up. It means understanding that doubt is not a personal flaw, but a natural reaction to stepping into significant leadership moments.
If you are a founder at the peak of your career and feeling imposter syndrome, here is the most important reminder:
You are not an imposter.
You are a leader who understands the weight of your decisions.
You are aware.
You are responsible.
You are engaged.
And that is exactly what the next chapter requires.
You do not need perfect certainty to lead well. You need perspective, self-awareness, and the ability to see yourself and others as real, complex human beings. That is where confidence grows. That is where clarity emerges. And that is how founders lead powerfully through the moments that matter most.
