The ubiquity of self-criticism among leaders

Wondering if someone else might be better at your job than you are? You are not alone.

Matt Munson
4 min readNov 6, 2022
The ubiquity of self-criticism among leaders

Originally posted at Subscribe here for regular updates.

I feel not enough nearly all the time. I constantly wonder whether the company would be better led by someone else. Someone who actually knows what they are doing. I feel like I do not know what I am doing. And the feelings of self-hatred come daily.

Reading the words above, you might assume they were spoken by the CEO of a failing company. The reality is quite the opposite. The company has been in the press frequently of late having received tens of millions of dollars from a top-tier Silicon Valley venture capital firm.

The company is by all accounts thriving. What is more, the company’s investors and employees seem to adore this founder. The investor who connected us wrote a glowing email about her intelligence, care for her team, and her openness to growth.

And yet, on our very first call, this confession of self-doubt and self-hatred came quickly.

As a coach, I witness daily a truth that I was oblivious to as a young founder: what is going on on the inside for nearly every leader is markedly different from what is going on on the outside.

This particular leader, like most I meet, shared feelings of extreme loneliness. She was exploring coaching in large part because there was no one else in her life with whom she felt she could share the full truth of her current experience.

I wish these experiences of loneliness, isolation, and self-doubt were the exception. Sadly, they are not; they are the norm.

In startup culture, we love to build up our mythical CEOs. Jobs, Musk, Dorsey. We tell stories of these giants and build them up like the gods of our age. It is never their humanity or vulnerability we praise; it is the parts of them that seem superhuman, even robotic.

We love the photo of Jobs sitting alone in his home in Palo Alto: void of family, friends, or even furniture.

We lap up stories of Musk sleeping on the factory floor.

We idolize Dorsey as a larger-than-life figure, the only savior who could drop back into Twitter and set the vision that escaped all others.

The fueling of these myths serves a purpose in the system. Anxious investors repeat them to founders they hope will sacrifice all else in their lives for the success of the business. Founders looking for a sense of significance, or a model of success in adult life, hold up these stories as a standard of a company well-led or perhaps even of a life well-lived.

Many of us founder types had experiences in childhood that set us up to embrace such myths. Many of us were told at a young age we had a unique ability in school or other related areas of achievement. We were told how special we were.

For some of us, those who should have been ensuring we felt safe and loved failed to do so. And so our ability to achieve outside the family became our only trusted way out. Many of us came from families where we were expected at a young age to be the stable one, the mature one, or the conciliar of one or both of our much older parents.

One way or another, many of us arrived at adulthood primed to lean into this myth: that some people are special or set apart and that leaders are those kinds of people. At least the great ones. We step into our own early leadership roles holding up these icons as our model.

The costs of entering into our leadership roles mimicking these icons are significant. Having spoken with hundreds of young leaders holding these models for their own success, I can feel the grief in my chest as I write these words even now.

As leaders, we would do well to welcome our own humanity and at times even our own frailty. We would do well to invite the humanity of those we seek to lead.

As investors, we would do well to check in with our portfolio CEOs as humans, not simply as operators.

You are not a robot. Neither was Jobs. And that, my friend, is wonderful if inconvenient news.

Originally posted at Subscribe here for regular updates.



Matt Munson

CEO coach @ Angel investor. Startup founder. Committed to helping leaders feel less alone in the journey.