The case for self-awareness and humility in entrepreneurship

If you spend a few minutes reading online advice to entrepreneurs, one thing becomes clear from the start – entrepreneurs are encouraged to be arrogant.

‘Fake it till you make it’

‘You can be often wrong, but never uncertain’

‘You have to be your own walking billboard’

‘Steve Jobs was arrogant’

And the list goes on and on.

This shouldn’t come as a surprise. Start-up literature is a reflection of society – and for years, we have declared confidence and high-self esteem as the cure for all social and economic ills. And social media is the fuel to professional curation for personal branding. I mean you need to possess some form of reliability and boldness – not just to convince the investors of your worth but also yourself, so you can endure long dark days of ‘hustling’. But this practice has created a massive disconnect between headline reading and practitioner-ship. If we keep pushing the narrative that everyone needs to be number one – a lot of people are going to lose.

From my own personal experience, I’ve found that the traits that separates good entrepreneurs from the great ones are self-awareness and humility. This is not some new-age call to disregard your self-worth. Being humble doesn’t mean to think less of yourself, but rather to think of yourself less.

I remember listening to Ben Silbermann in 2011 when Pinterest had less than 10 employees and millions of user. He never bragged about the rapid growth they were going through. Or the fact that he came up with this ground breaking idea. He genuinely was concerned about the impact of scale on the community. He spoke of ‘our company’ not ‘my company’. And his humility has served him well.

The case for self-awareness

Confidence and power are often prioritised in leadership roles, but shouldn’t self-awareness be the top criterion? Don’t get me wrong – I have often had to project confidence to sell an idea or rally up my team – but ‘projection’ should never be confused with ‘pretension’. Self-awareness allows us to recognise our strengths but also acknowledge our weaknesses. It is also the ability to recognise how we fit in with the rest of the world.

When entrepreneurs are self-aware, they know how to hire teammates who are strong in the areas where they themselves are weak. And additionally, their humility allows them to accept the fact that someone on their team may have an idea that is even better than their own. By building more self-aware teams, we can persevere through adversity and learn at ever increasing rates. Highly functioning teams have the courage to own their behaviour and achieve any goal and carry out any plan.

Jim Collins discusses the role of self-awareness in leadership in his seminal book Good to Great. He suggests that great leaders are a study in duality: modest but willing, shy but fearless.”

I’ve had the privilege to meet and work with many great entrepreneurs, and when they combine self-awareness with exceedingly high levels of intellect and curiosity – BOOM – they’re guaranteed winners! Self-awareness is my number one predictor of future success because it essentially determines our capacity for growth.

On your journey of being an entrepreneur, you will likely face extreme hardship on the road to success – so being self-aware and humble will ensure that your team and your investors follow you when times are tough as they did when times were good. Being humble will make you question vanity metrics and celebrate meaningful ones. It will lend your story credibility.

These aren’t traits you are born with. It’s something you practice. So in the middle of reading all the blog posts about exuding confidence, try replacing some of it with self-awareness and humility. Your start-up may be better for it. And you certainly will be.

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