An endless series of difficult but achievable hills

Lightning rarely strikes. Instead, achievement is often the result of stepwise progress, of doing something increasingly difficult until you get the result you seek.

For a comedian to get on the Tonight Show in 1980 was a triumph. How to get there? A series of steps… open mike nights, sleeping in vans, gigging, polishing, working up the ladder until the booker both saw you and liked you.

Same thing goes for the CEO job, the TED talk on the main stage, the line outside the restaurant after a great review in the local paper.

Repeating easy tasks again and again gets you not very far. Attacking only steep cliffs where no progress is made isn’t particularly effective either. No, the best path is an endless series of difficult (but achievable) hills.

Just about all of the stuck projects and failed endeavors I see are the result of poor hill choices. I still remember meeting a guy 30 years ago with a new kind of controller for the Atari game system. He told me that he had raised $500,000 and was going to spend it all (every penny) on a single ad during the Cosby show. His exact words, "my product will be on fire, like a thresher through a wheat field, like a hot knife through butter!" He was praying for lightning, and of course, it didn't strike.

There are plenty of obvious reasons why we avoid picking the right interim steps, why we either settle for too little or foolishly shoot for too much. Mostly it comes down to fear and impatience.

The craft of your career comes in picking the right hills. Hills just challenging enough that you can barely make it over. A series of hills becomes a mountain, and a series of mountains is a career.