Are you in the process of dying happy? What would you dream or do or start or create if you knew for certain that if you didn't you'd feel the stabbing sting of regret at the end?

I am blessed with an amazing network of entrepreneurs whose collective wisdom could easily tackle running the universe. I've also had and have some amazing mentors, friends, guides and climbing partners. My kids are unafraid of knocking me down a peg and my spouse understands who she married. And I have a coach.

Phil has been a consistent source of counsel and perspective and the occasional smack down in the face of stupid shit I've done, am doing or thinking of doing. He's also the older man with whom I have the closest relationship. My father does not play that role. His dad did not play it for him either.

My father was put up for adoption by his father – a famous Canadian surgeon working in London – and his aristocratic mistress. Later he was run out of Jamaica by the well-to-do parents of his first wife before his daughter was even born. History repeats.

Our father's history, which is really our grandfather's legacy, has hung over the heads of all three of us kids. In each our own way, we have had a lifetime of overcoming deep feelings of not being good enough. And we are not alone either. Canada is a colonial nation and despite the so many ways we are a world-class country producing world-class scientists, philanthropists, artists, athletes and entrepreneurs we seem to be mired in some sort of National Inferiority Complex. And it is complex.

Inadequacy offers of deep well of motivation to create, excel and achieve. Steven Spielberg, for example has been vocal about how his insecurities as a man have led directly to his greatest film achievements.

The life of P.T. Barnum is the subject of The Greatest Showman. He grew up poor and without the status of the swells he so wished he could be. He spent his life trying to prove himself to the upper classes. My guess is that my grandfather could relate as they grew up in similar times.

P.T. Barnum in the end created something I think is marvelous. I wonder if he thought it is was marvelous. I hope he died happy, but I have my doubts. We are all dying who are living. The reverse is not automatically true. I'd like to be content when that perhaps inconvenient moment happens.

Within the comedy and drama of life is a paradox: if some of my greatest creations spring forth from deep set feelings of inadequacy, how am I ever supposed to feel content? Perhaps the solution lies in the journey rather than in the destination.

I am in the process of creating what's most important to me, even if it's not obvious in the moment.

If I look up one day in the cold and the dark and the rain and see Death coming my way, that may be the only position to exit happy in. With Hope. And Grace.

I am grateful for my grandfather's affair. I'm here and over this next three years I am spending myself on what I hope is my work of art – a book every three months to share what I have learned from my network of entrepreneurs, mentors, friends, guides, climbing partners, favorite speakers and writers, kids, parents, wife and Phil. I have priced each book at $19.64, the year of my birth. I think it's good value given what all these people have to share. Order yours here. Please share this article. Art's better when seen and heard by the people who need to see and hear it.