The Path to Progress, Fulfillment & Fun: Taking Risks

No risk, no reward. 

This is the rule in business, in investing and in relationships. All the wonderful things that make life special. 

Growing up as the eldest son in a Taiwanese immigrant family, I’m as conservative as they come. The regular path was what was drummed into me. Get good grades in school (that did not quite happen), get a good safe job at an established company or organization. Safe but boring. 

But when I turned 22 I left Canada in search of adventure, summer school in England, backpacking in Europe. Then it was off to Asia for a 2 year stint, before ending up in San Francisco. 

I look back at all the best things that happened to me. Backpacking in Europe and meeting some fascinating people, living in Taiwan and meeting my wife which led to my wonderful daughter Amber. A fulfilling career in a fast growing startup, an international career at Yahoo! And now a venture capital investor & sometime newsletter writer. None of which would have happened without taking some risk, a bit of luck and lots of hard work. And I should add, all off the beaten paths of my peer group and family expectations at that time. 

Life is about taking chances. Not stupid jump off the Golden Gate Bridge drunk without a parachute risk. But calculated risks. 

In venture capital and Angel investing it’s called Asymmetric risks. Ones with unfathomable payoffs but with the potential loss of only what you put in. 

And this is not the choice of  joining Goldman Sachs over McKinsey. That’s not really a risk frankly. Real risk is joining a no name underfunded technology or biotech startup that may die in a few months but has the chance to dramatically improve how we live. That’s true risk. 

You never know where the random meeting, call or investment will take you. It could lead to life changing wealth, lifelong friendships, a life partner or a nugget of insight that will change how you view the world. 

There is this scene in Nolan’s classic sci-fi movie “Inception”, where the Japanese industrialist says to the protagonist: “So do you want to take a leap of faith….or become an old man filled with regret… waiting to die alone.”

An interesting and fulfilling life requires taking risks. Progress in life and the world requires taking risks. It requires a leap of faith. Many of them, all the time on a regular basis. Be brave and take action. You may be surprised by where life takes you….in a good way.