Reboot Podcast Episode #34 – Self-Actualization is Limitless – with Henry May

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Episode 34 // March 3, 2016

Your vision will become clear only when you can look into your own heart. Who looks outside, dreams; who looks inside, awakens.


Henry May

Henry May

CEO and Co-Founder of CoSchool

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Episode Description

“Work is difficulty and drama, a high-stakes game in which our identity, our self-esteem, and our ability to provide are mixed inside us in a volatile, sometimes explosive ways.” from David Whyte in his incredible book, Crossing the Unknown Sea: Work as a Pilgrimage of Identity.

That volatile, explosive mix is a gift. It presents a tremendous opportunity for us to do our own work, our inner work, and further develop our own understanding of self. In our conversation today, Jerry is joined by Henry May, founder, and CEO of CoSchool, based in Colombia.  Henry comes to Jerry with this very issue: How might the journey of entrepreneurship, specifically his own, open up new opportunities for him to grow? How might entrepreneurship be a powerful journey of self-actualization? Or said more directly: How might he use his work at Coschool to do the real work on his humanity?

Henry May on Twitter

Show Highlights

Top Quotes:

“The journey of discovery of self is a really powerful journey.” – Jerry Colonna

“Being an entrepreneur is not necessarily about all the tools you have access to around you. It is about going inwards, and finding out what you’ve got inside.” – Henry May

“I started to see the successful entrepreneurs around me were those doing really interesting and meaningful work, and connecting with themselves.” – Henry May

“We start to lose access to some very powerful forces within ourselves when we don’t spend the time to actually understand who we are.” – Jerry Colonna

“To protect myself, I was a bully as much as I was bullied by other kids.” – Henry May

“The ability to get people to gang up on other people is a part of the bully’s arsenal.” – Henry May

“In these kinds of moments of self-inquiry, the impulse can be really strong to tip over into self-denigration. Let me explain to Jerry, what a shit I am. You are not a shit. You are a complex and multivariable human.” – Jerry Colonna

“You are not a shit. You are a complex and multivariable human.” – Jerry Colonna

“Being CEO of a startup in a foreign country, in a foreign language, and with team members from a different country, means that there is some fear at my core that I am out of my depth.” – Henry May

“The ultimate fear is that things go wrong, and the dream to which we are sacrificing so much for disintegrates, and I have played a role in the disintegration of that by not being the right person at the right time.” – Henry May

“As the opportunity gets bigger, it feels like the risk is getting bigger.” – Henry May

“We work with kids from private schools, public schools, rural communities, and urban communities, and they see the same need in all of them.” – Henry May

“We have all worked for bosses where you feel like you are being used, and you feel this way because you are being used.” – Jerry Colonna

“ It’s a challenge that soft skills are not so measurable, but they are limitless.” – Henry May

“It’s the movement towards this awakening that is the most important thing.” – Jerry Colonna

“There’s an endless realm of depth, growth, and self-actualization.” – Jerry Colonna

“The more you can truly love who you are and what you do the more that little voice of fear starts to go away.” – Henry May 

“Whatever job or decision you make, if you continue to live life wholeheartedly and with love, you should be okay.” – Henry May