When Alexander saw the breadth of his domain, he wept for there were no more worlds to conquer.  —Plutarch

Of all the “good” problems to have, the best might be “post achievement depression”. It comes by way of the arrival fallacy—a term coined by the psychologist Tal Ben-Shahar from his excellent book Happier. The idea has been around for a while but it’s heralded by the phrase “I’ll be happy when ….” When I get that career reward, land that publication, earn that raise, retire, etc.

We work hard for those goals, imagine what it will be like to attain them, build up the anticipation, and then watch the anticipation crystallize into expectation. Expectation diminishes the joy. Then we fulfill the goal and, well, whoop-de-doo.

Like a dog chasing a car, we’re left to wonder what’s next once we actually catch it. Do we just chase a bigger car?

Probably. Because the chase is what’s most fun. Steve Jobs frequently said the journey is the reward. He was right.

To that end, the trick might be diversification. Multiple chases. Built on something more enriching than a mere single outcome. That makes for a completely different game and, from a strategy standpoint, it has better probabilities. It’s the equivalent of developing a portfolio as opposed to investing in a single stock. Not a big portfolio, mind you, but still something more than one chase.

In a broader portfolio, profits don’t come from a single investment, a single chase. They come from a collection of independent, uncorrelated investments. It’s a garden with multiple crops.

But this is nuanced, see, because you can’t try to be a business mogul and the world’s greatest harmonica player at the same time. There is still an overarching goal that drives the design of this portfolio and the sequence of action.

There are more details to come because this is another fundamental idea in this week’s book review, “How To Fail At Almost Everything And Still Win Big.” For now, just know that this effects everyone—even the best of the best. Yesterday featured a story about Michael Jordan. He’s the greatest basketball player of all time but, after three NBA championships and an Olympic gold medal, felt like a proverbial Alexander and had to find some other realm to conquer.

So he went to baseball. Another car to chase. One that made him “feel like a kid again.” It wasn’t a bad move. Not at all. Just further proof of our insatiable need for a chase rather than a catch.

Photo of a wonderful doggie by Stewart Black from Flickr