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Impostor Syndrome - it doesn't care about your background


A few years ago I joined the Entrepreneurs Organization. It’s a very cool tribe, with a global reach. I didn’t quite understand it at the very beginning, I thought it was a learning organization through which I could study at the world’s best schools.


Now, that is true, but it’s a whole lot more. First, I met some of the local members in Cape Town. And they were amazing people, doing amazing things in business and life – and I was inspired.


Then I jumped on a plane to Dubai to go to a 3-day seminar led by two Professors from Harvard. The crowd there was mostly middle-Eastern. And most of the delegates had businesses way bigger than mine. And I mean way bigger.


That’s when I realized there is also a strong element of second-generation leaders in the organization, guys who are now leading their family businesses. And some of these businesses are massive, the market leaders in their respective countries.


Having been groomed for leadership in our market-leading family business many many years ago, I found myself wondering: Do they feel like I felt? Despite outwardly being very confident, were they inwardly besieged by a doubt that they were good enough? Did they wonder if people spoke derisively about them behind their back, and did they care like I did how many even openly demeaned them and their accomplishments by citing their “Free ride”?


There was little sign of it.


But, I’m sure it was there. You see, that’s kind of what our organization is built on. A peer-to-peer organization where, in your Forum cohorts, you can just let your guard down. And tell people that you feel inadequate, you don’t know what the hell you’re doing, and you have no idea what to do next.


I recently watched an interview Michelle Obama gave on the topic of Impostors Syndrome (check it out below) and it was enlightening. The same feeling I had as a privileged white dude was shared by her as not only a member of a minority but also a female making her way in business and an impactful life. Only it came from a wholly different angle.


There weren’t a lot of people telling me I didn’t belong as I grew up. In a way, I probably felt quite a bit of entitlement. But as a direct correlation, I always tried to overcompensate for a fundamental feeling of inadequacy. Having been given such a disproportionately big jumpstart in life, I frequently didn’t know how to be properly grateful for it or how to leverage it without guilt to make a bigger impact. I spent a worrying amount of time trying to just fly under the radar and not screw up.


For Michelle Obama, there were a ton of people telling her that she didn’t belong. Whether she felt this based on gender or colour, it speaks to her fortitude that she channelled this into something positive. But for a lot of people that incessant messaging becomes part of their DNA. It limits them, comes to define them in a way. And they don’t get to their full potential as a result. She is, unfortunately, the exception not the rule.

I also reckon a lot of the aspirational brands in the world have built their business on Impostor Syndrome. Whether it’s Rolex, BMW, or Chanel, people will throw an inordinate amount of money at being seen to be successful.


But the more I study this, the more it appears to me that Impostor Syndrome is one of the great undiagnosed ailments of our time. That you could directly link psychological conditions such as severe anxiety or depression to not dealing with the feeling of persistent inadequacy and alienation.


So what to do?


Well, I decided to study some great leaders and just great people. And this is what I found:


They do the work. And they cut themselves a break.


And by the work, I mean they take the time for reflection, introspection, and inner work. Their lifelong journey is to come to grips with who they really are and what drives them, finding ways to channel their inner gifts and mitigate the influence of their demons.


And as they wrestle those demons, they somehow manage to channel them. Demons can be useful, as long as they don’t have the final say.


I really liked this Ted Talk by Mike Cannon-Brookes, founder of Atlassian. This guy has succeeded by any given metric available to us – and yet he still struggles with Impostor Syndrome. But he reckons it fuels him. It drives him. And not just in work – in marriage.


To his hypotheses, a truly successful union is where both partners feel slightly out of their league. As if they should count their lucky stars every day to wake up next to the other. Also keeps them hungry and motivated to show up every day, and be at their best for the other.


Food for thought hey.


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