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99 Problems

A mentor doesn’t show you how to do something. They challenge you to be better, to level up. They aren’t dumping their work on you, they are inspiring curiosity.

Earlier this year, my boss challenged me to become a more creative problem solver. Eventually it turned into a 30 day Challenge called 99 Problems, where we learned to cultivate a more curious mindset. We would try to diagnose three problems a day, ranging from mundane to significant, to practice seeing opportunity in all parts of life. We evolved that into brainstorming 99 solutions, where we turned that curiosity into problem solving.

One night we sat down to discuss our problem solving and had the idea of drawing two random topics and connecting them into one crazy innovation. That moment of creation, repeated over and over, draw after draw was intoxicating. It was an inspired conversation, and my only regret was not recording it in some way.

Riding the high of that night, I went out and bought a microphone, downloaded some audio editing software and started learning how to make a podcast. Quickly the Idea Machine was born, and while we had early growing pains, it’s starting to develop into an exciting new Gameshow.

Who knows where the Idea Machine will take us, but that’s not the point of this article. The takeaway is that a good mentor will rarely give you a straight answer to anything, instead encouraging your own exploration. They will be there to prod you at the right moments, but they will also know when to step back to let you find your own path.

If I am ever lucky enough to mentor someone, I can only hope to inspire their curiosity, and enable their personal exploration like my manager once did.

Published inLearn