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Adii Pienaar

Family man, seeker and learner. Revealing my inner-poet. 2X Founder: Conversio (acquired by Campaign Monitor) + WooCommerce (acquired by Automattic. Ex-Rockstar.

Toxic Entrepreneurial Masculinity

"Just pull yourself up by your bootstraps."

"Impossible is nothing."

"Just do it."

"You are the master of your own destiny."

As a collective, we have contorted what it means to be an individual on an entrepreneurial journey. We have singled out the entrepreneur as the one with all the opportunity, privilege and power to build businesses, create immense wealth and - along the way - guide greater society into a Dystopian (supposed) Utopian future.

Professor Scott Galloway probably coins the best term for this ("sociopath with a Jesus complex") when talking about the recent WeWork bailout:

There's so much about the modern-day entrepreneurial archetype that resembles (and perpetuates) vast parts of toxic masculinity: There's an aggression and dominance in ambition and competition, where we believe that hard work should always pay off. Almost as if entrepreneurs are entitled to success purely because they show up and do the work. Mostly ignoring how they do that or what the consequences are, because the end justifies most means (and all means, considering the means that we all know are wrong, but we manage to keep those secret).

More than that, the thing that concerns me most is the over-reliance on self. The notion that, as an entrepreneur, the weight of the world is on my shoulders as I push this rock up the hill. With all of the odds stacked against me. With so many risks I need to take. So many people that I need to persuade to join this journey (as investors, customers, team members, partners etc). Beg, borrow and steal. All of it my responsibility (and right) as an entrepreneur.

But: no pain, no gain. Right?

No wonder we both see the rich only getting richer, whilst more entrepreneurs are speaking out about depression. Neither of these are intended or desirable outcomes.


I don't think that this is a question of gender (male versus female, men versus women). The more important challenge we have is to create a much better blend of feminine and masculine energy and traits when we speak about entrepreneurs and entrepreneurship.

Today's truth is that the historic patriarchy rewards many of those toxic masculine traits (sometimes exclusively so). Even when it is women that are made to play by those rules. It's that toxic model that we all have a responsibility for breaking down and evolving to something better.

There's a version of entrepreneurship and an expression of self here that I believe is closer to the feminine nature. One which does not understate the importance of a confident individual that decides to manifest their magic and ideas in this world, and has the perseverance to show up repeatedly - when it's fun and when it's incredibly tough - to create something of value.

But also one that has a softer and kinder perspective on self; one where the first step is always inward. Finding stillness and clarity. Reconnecting first with the magic that is already within us and only thereafter finding ways for that to emanate beyond us.

The book, The Art of Possibility, has this beautiful quote to support this idea:

β€œIn the measurement world, you set a goal and strive for it. In the universe of possibility, you set the context and let life unfold.”

As an entrepreneur we do have many responsibilities and we will always have to do hard things. But those are not the responsibilities and hard things as we know them today.

The bigger challenge here is to find ourselves before we find customers.

It's about learning to be still before we get stuck in busy work.

It's aligning our actions with our values, instead of pursuing the creation of value.

And it's about being a single node of positivity and energy, a facilitator for our collective magic, rather than ever believing that the I / Self is the only entity that can create something of value in our society.

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