Ask simple questions

Ask simple questions
Punch card.
“Doesn’t logic tell us that simple questions should also be the easiest to answer? No. Simple questions can be profound, and answering them requires us to make stark and honest—and sometimes painful—self-assessments.” — Peter Drucker, The Five Most Important Questions You Will Ever Ask About Your Organization (1993)

Jack Dangermond is an unlikely billionaire. He started his company (ESRI) in 1969 out of his beat-up old station wagon. Yes, his station wagon. He didn’t even have a garage. The category he would go on to dominate didn’t exist in 1969. He created the category. And Jack didn’t raise any venture capital money. Instead, he built the company from scratch and he still owns it.

Jack started out painstakingly feeding punch cards into the earliest computers to launch the field of geographic information systems (GIS). As I write this in 2024, ESRI is estimated to be valued at $5.5 billion and after 55 years of fierce competition, ESRI is still the dominant GIS vendor. No company even comes close.

Jack Dangermond is no ordinary entrepreneur. He’s a legend, an elusive and eccentric character that few people get to meet, let alone spend time with. But in the summer of 2002, a friend of mine, who worked at ESRI, arranged for me a private audience with Jack Dangermond himself. I was star stuck, dumbfounded, and scared out of my wits. I wasn’t supposed to be interviewed that day, let alone by Jack Dangermond himself. But that’s what happened.

I spent two hours with him. It did not go well.

As soon as he sat down, Jack Dangermond dispensed with all pleasantries and pounced with one simple, profound, and utterly unexpected question: “what do you love?”

Then he sat back and watched as I devolved into a child. He continued to barrage me with simple questions. That day I learned a lot about myself.

I knew Jack Dangermond only gave me the gift of his precious time out of respect and admiration for my friend who worked for him.

For weeks and months and years after that fateful meeting, I pondered the implications of my disastrous audience with the legendary Jack Dangermond. I resolved to answer the simple questions he asked me.

“We needed to stop asking about the meaning of life, and instead to think of ourselves as those who were being questioned by life—daily and hourly. Our answer must consist, not in talk and meditation, but in right action and in right conduct. Life ultimately means taking the responsibility to find the right answer to its problems and to fulfill the tasks which it constantly sets for each individual.” — Viktor E. Frankl, Man's Search for Meaning (1946)

Ask simple questions

Ask yourself simple questions, then do your best to answer them. What do you love? What do you hate? What do you fear? What makes you lose track of time? What are you willing to die for? Who are you willing to die for? What are you willing to sacrifice for your dreams? What are your dreams? What is your plan?

Some answers will take years to arrive by, and some answers may change over time. It may also take years to craft the right question. That too is an art into itself.