If you could ask one person, alive or dead, only one question, who would you ask and what would you ask?

Questions are a powerful thing. They are the heart and soul of good conversations. They guide people to think about certain things and ultimately help people understand one another better. I love questions. But a key part of powerful and insightful questions is the person you ask.

Imagine asking a commercial airplane pilot a detailed question about frying fish on a professsional level. Great question, wrong person. Bobby Flay would have been perfect. But that’s what today’s question really is. Given the opportunity, what one question would you ask anyone dead or alive?

Here’s my thoughts and answer to this question.

There are so many great people to speak with in the world. There’s Elon Musk, Mark Zuckerberg, and Jeff Bezos that’s alive and killing the game. I could only imagine the amounts of knowlegdge I could gain from speaking with one of the them. And that could be one question’s worth of knowledge. I know my life would be changed. It was changed before when meeting Mark Parker, the CEO of Nike.

The only difference is there was a lot more than one question to work with. But that was real life. With an amazing opportunity like this, I can only imagine what could be garnered from the people dead. Naturally, it feels like more of an impossible moment to ask that question to someone who is gone. So goodbye to the startup kings of our generation.

So with a lot of thought there’s two people I think of that would spark my interest to ask questions. The two would be Houdini the great magician who died in his prime or Steve Jobs the business legendary who revolutionize the world with sleek consumer technology. They’re both people I think about often and whos stories I feel have inspired many aspects of my life.

But there can only be one. Magic is a hobby of mine, business is my calling. So I would choose to speak with Steve Jobs, one of the greatest entrepreneurs of our era. And the question I would ask him is a very simple one. It can be answered by many people. But I think him being so wildly successful all to have is life cut drastically short gives him a unique perspective.

I would ask Steve, “Was it all worth it?” That’s it. He’s lived an amazing life. He had more money to his name than some small countries. He accomplished unfathomable feats that no one can take away from him. But it all took an unrealistic amount of dedication and obsession to his craft. He had to make many big, life-changing sacrifices to reach his levels of success.

My life and goals have pulled me in a similar direction. I’ve spent a lot of time obsessing over the mechanics and details of my business and career path. It’s sometimes an inhumane level of dedication. I know that the levels of success I strive for requires these levels of sacrifice. That’s something I willing to do. What I don’t know is… Is it all worth it? And I think all it takes is a small yes or no from someone like Steve Jobs that achieved it all and lost it too early, to forever impact the outcome of my life.

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