When it comes to progressing in life, before the what and how must come the why.

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The brilliant Greek general Pyrrhus was eager to sail to Italy and use his considerable military prowess to subdue the Romans and revive the glory of his cousin, Alexander the Great.

Pyrrhus’ friend, the philosopher Cineas, asked him what they’ll do once they’ve defeated the warlike Romans. Pyrrhus replied that once Rome falls, they’ll have little trouble securing control of the rest of Italy and its vast wealth.

Cineas thought about the answer for a moment and then asked what they shall do once they’ve taken Italy.

“Sicily, nearby, stretches out her hands to us!” Pyrrhus said, followed by a quick explanation of how easily they would bring this politically troubled territory into the fold.

Cineas agreed that Pyrrhus’ plans to absorb Sicily next sounded plausible and asked if the capture of the island would end their expedition.

Quit to the contrary, Pyrrhus said, Sicily would be used as a staging ground to sail to Libya, Africa, and Carthage and extend his empire to include these great lands. And once he has conquered so much territory, Pyrrhus said, how could any of his remaining enemies in Greece be able to resist him?

They surely couldn’t, Cineas admitted, and such victories would give Pyrrhus the military and economic muscle needed to win back Macedon and then the rest of Greece. But Cineas had yet another question: once they’ve established their dominance everywhere, Cineas said, what shall they do?

Pyrrhus thought about it and laughed, answering that they could then lead a life of leisure and entertainment and daily drinking parties.

Cineas interrupted his friend to inquire as to what exactly was holding them back from having a drinking party now. Why did they have to conquer the world first?

Pyrrhus had no answer, and ultimately embarked on his ill-fated Italian and Sicilian campaigns, which proved too costly in men and material and were eventually abandoned.

Now, what’s my point for telling this historical anecdote? Well, it strikes at the heart of an issue we must face in all our endeavors if we are to succeed, and that’s the issue of…


Why start if we may have to stop one day? Why sacrifice the time, comfort, money, or energy? Why hang our goals over heads like Swords of Damocles?

In a culture such as ours that worships work ethic and productivity, these questions are especially important. Without purpose to guide us in our lives, we can easily fall into the mindless pursuit of busyness for its own sake. (Click here to tweet this!)

So take anything you’re working toward or considering–a better body, a better job, a better relationship–and explore the question of why. How well can you answer? How does it make you feel?

If your answers lack conviction or if your enthusiasm cracks under the inquiries, you’re not going to make it. When things get tough–and they always do–you’re going to start asking these questions again. And if you can’t find inspiration in your answers, you’re going to find despair.

The interesting thing about whys is I’ve noticed that many of the greatest achievers in history were not driven by flowery ideals but instead by stark, simple ideas.

At his peak Tiger Woods was the greatest golfer to ever play the game. He didn’t just win tournaments–he crushed his competitors in a way the sport had never seen, leaving them so far behind they simply had no hope of contesting his lead.

In an interview conducted with Tiger during his prime, he was asked what drove him to practice so hard and play so dominantly. His reply? One word: “winning.” The interviewer paused for a moment, no doubt expecting something more profound or inclusive, and asked if that was really it. In golf, that’s it, Tiger said.

I love that. There’s incredible power in its simplicity.

When you’re knee deep in shit and don’t know North from South, lyrical musings won’t cut it–you need a single, definite, primal concept to keep you moving. You don’t need need a handful of sparklers; you need a chunky ember that never loses its glow.

Going back to Pyrrhus, one of the most gifted generals of all time, why did he want to go through all the trouble of building his empire? Was it really to rest in the end? Of course not.

Like his cousin before him, who had conquered most of the known world by the age of thirty, Pyrrhus’ why was glory. While that word may inspire nothing in you or me, it represented the essence of life to great military commanders like Pyrrhus and Alexander.

And that’s the real point of this article: if you take the time to find the whys that inspire you, then you too have the opportunity to see what you’re really capable of.